Key Lime Sailing Club and Cottages Logo

Welcome to our unique little hideaway. Secluded, serene, and perfectly located, our self-contained cottages have everything you need for a relaxing waterfront vacation.

There are no hidden charges – your stay includes:.

  • Unlimited private sailboat use
  • Snorkeling equipment
  • Stand-up paddle boards
  • Fishing gear
  • Use of BBQ grills
  • Onsite parking

In the evening, just walk or paddle around to local dining and dancing. Or stay on site and enjoy Key Largo’s incredible sunsets from one of the area’s most intimate settings… the Key Lime Sailing Club & Cottages. Easy to reach, hard to forget!

Key Largo Snorkel Charters

This was my 10th year of staying at KLSC in early March – it continues to be my vacation site of choice – and I’m already in the book or 2016. Great location, amenities and staff. It doesn’t get any better than this.
We had the most wonderful vacation. I want to thank you and your staff. It felt like everyone went out of their way to see our vacation was more then we expected. And it was. If anyone ask me where to go on vacation I only have one answer, “The Key Lime Sailing Club!”
Totally enjoyed our trip,staff was great, my wife had never sailed. She is hooked now, will be back soon, thank you for a great vacation.
Can’t say enough about the staff, perfect! Enjoyed all the watercraft available for use, kids loved the place:) Really enjoyed our stay, Talofa was great, the people and staff really made the trip awesome!
We had an amazing vacation at the Key Lime Club and so much fun sailing in the Keys! The staff were MORE than helpful and so fun to talk with. Loved the relaxed atmosphere, the family feeling at the tiki, and being able to use the water toys was a big plus. Give our love to Captain G, Irene, James and CJ! And thanks again for the sunset sail and the hospitality! We’ll surely recommend the Key Lime Club to others:)
We had a fantastic time. All of the water equipment was awesome! It was so nice not to have to worry about bringing all of that stuff with us. Our home was also equipped with tons of movies and games. What an excellent option for a family to have. Thank you KLSC!
We had a great time at KLSC. The staff was especially wonderful and attentive! We loved it there.
Sailing was great and your staff was very accommodating and top notch.Hello to Capt. G, Irene and Jeff
Perfect for our family vacation. Not over commercialized and a great place to get outside and discover things! Out boys loved it.
We were so pleasantly surprised at Key Lime North! Breathtaking, beautiful, and very hard to leave! Sandra, Nick, and Heather were wonderful, helpful, and will be our lifetime friends. Paulie made everything special including remembering birthdays and beyond! Captain Sheldon was a fantastic sailing instructor. Nothing beats this vacation!
We LOVED our stay and your hospitality. Everyone went above and beyond to make the stay enjoyable, including John from Michigan who took us out in his sailboat one afternoon. That was definitely our treasure of the week, spending time visiting with him while sailing. Diamond in the rough, so glad we stayed! Definitely would book here again if the Keys were our destination.

We Still Have Cottages Available, Request to Book!

Key Largo Cottages

Our Sailboats

If you’re an experienced sailor we invite you to use one of our own 22′ sailboats with your cottage rental at no additional charge. there’s no better way to relax and enjoy the keys.

Our 22 foot Catalina or O’Day single-masted sailboats are perfect for cruising the calm waters of Florida Bay. Just grab your cooler, walk to our dock, and point the bow into the horizon. Explore the Florida Keys in style! Leave and return when you like…after all, you don’t want to be tied to any schedule when you’re on vacation.

Sailboats

And if sailing isn’t for you, try our kayaks, canoes, standup paddle boards, rowboats, or even one of the floats we make available to our guests at the dock. The point is: take to the water! It’s the Florida Keys way of life!

Even relatively new sailors can enjoy the Bay on one of our easy-handling day cruisers. It’s great family fun, and a big part of the reason Key Largo Cottages remains so popular with our guests. Find out for yourself!

22′ SAILBOAT RENTALS

Rent a 22’ Catalina Sailboat and sail around the beautiful Key Largo bay area for only $300/day plus taxes. Note: We mainly rent the cottages with a free sailboat but on a case to case basis we may have an extra sailboat that we can rent out. Just call when you are in town and we will see if we can help you get your sailing needs taken care of.

Morning Star Sailing Charters Logo

Captain Only Charters

Captain only charters your sailboat. your captain.

florida keys rental with sailboat

Meet your yacht at our home in Soper’s Hole

“Know your charter is going to be perfect, without any drama.”

florida keys rental with sailboat

Experience exhilarating Sailing and Nature.

“Discover the Islands of the Florida Keys.”

florida keys rental with sailboat

“Morning Star Charters.”

florida keys rental with sailboat

Let the day Start and stop when and where you desire.

“The Perfect Get-a-way”

florida keys rental with sailboat

“Enjoy the feeling of being welcomed into the Morning Star sailing family”

florida keys rental with sailboat

Sailing at it’s best

“Morning Star Charters is the longest established Sailing snorkeling Charter company in the Florida Keys.”

florida keys rental with sailboat

Enjoy self-prepared Meals from your well equipted galley while surrounded by incredible beauty

“All the water toys you could want, available to rent right here at Morning Star Charters.”

florida keys rental with sailboat

Morning Star Charters, Sailing, Snorkeling, Kayaking, Sunset Sails, Cottages and Sailboat Rentals in the Florida Keys / Key Largo. Sailing and land based Sailing Vacations.

Blue Ocean Yacht Charters

 Key West & Marathon, Florida

We specialize in private luxury yacht & sailing charters at affordable prices. we offer day charters as well as multi-day charters., why blue ocean yacht charters.

Blue Ocean Yacht Charters, located in Key West, Florida, makes yacht rentals affordable and life-changing.  We offer private multi-day bareboat charters to amazing destinations like The Dry Tortugas and the Florida Keys.  Just looking for a day charter?  Look no further.  We offer four hour, eight hour, and 24 hour charters as well multi-day charters.

All our yachts come fully equipped to make your private boat charter experience what you’re looking for. We offer motor and sailing yachts that provide the best boat rental experience.  

Accommodations

 waterfront accommodation.

“CONCHED OUT” is our 2 bedroom house, each with a Queen size bed. This unit will accommodate 4 people.

You can easily do a day trip to Key West or Everglades National Park

Our ideal location, the middle Keys, will allow you to venture out in either direction. You can easily do a day trip to Key West or Everglades National Park .

Key Largo is very famous for their John Pennecamp State Park which has beautiful patches of coral reefs. Sombrero Reef , off of Marathon, is also another great place to snorkel or scuba dive.

Hawk’s Cay Resort, only 2 miles down the road, offers scuba divers reef trips, with equipment. There are also numerous dive shops available in the area. For you snorkelers, we offer a small selection of “complimentary” snorkel gear.

Long Key State Park , which is 4 miles from our vacation rental units, is a great place for a walking tour of the old hammocks – the vegetation of the Florida Keys before development. There are lots of shorebirds, songbirds, and waterfowl; plus, many species of native palms and hardwoods. At this state park you can also rent canoes and explore the natural mangrove channels.

At our Florida Keys rental with sailboats , you have the use of our kayaks and bicycles – or just sit under the coconut trees with one of our good books from our library. Enjoy a Florida Keys romantic sunset from our dock, be sure to look for the “green flash”.

Reservations

Availability & pricing.

To request a reservation at conchkeysailboat, simply complete this form and click “Submit”. We’ll contact you as soon as possible to confirm the availability and finalize your reservation.

[contact-form-7 id=”171″ title=”Contact form 1″]

30 S Conch Ave, Marathon, FL 33050, USA

+1 305-340-9578

[email protected]

We are located on the island of Conch Key, mile marker 63, just past the Long Key Bridge. This bridge is approximately 2.4 miles. You will find the mile markers (small green signs) along the side of US 1. Key Largo is mile marker 120 and Key West is mile marker 0. Conch Key is on the bayside of U.S. 1.

We’re very proud of our reputation. Our vacation rental units are very clean and comfortable. Upon check-in you will notice colorful hibiscus flowers and conch shells scattered around the walkways and inside the rental unit.

Call for an appointment to tour the facility and visit with us.

Call +1 305-340-9578

Or email us at: [email protected]

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Get Away to Key West and Explore the Florida Keys by Sailboat

Did you know there's an international airport perched out in the Gulf of Mexico at Key West? Serviced by all major US airlines and with frequent flights from main airports in the East and South, Key West is so easy to get to. That's where you'll find our boat charter operators, who have a range of sail and motor boats for you to explore this unique corner of the USA.  

Along the Florida Keys the holidaymaking options are numerous. Enjoy the aquatic environment with countless opportunities to snorkel, swim, kayak, paddleboard and more, while totally relaxing on board, or ashore on one of the Keys' beautiful beaches. Enjoy an evening meal in one of the upmarket restaurants that dot the Keys, shop and enjoy the nightlife in the major centers of population, and get close to nature at one of several locations designated State Parks. 

While pandemic concerns are limiting travel options, consider Key West as your next boat charter vacation destination. Local ordinances reflect the need to keep everyone protected and make this a safe destination. The communities are welcoming and open for business. 

florida keys rental with sailboat

Some of the highlights to experience on a Florida Keys Sailing Charter Vacation 

Your Florida Keys adventure likely begins and ends at Key West, which is closer to Cuba than Miami yet connected to the US mainland by the 90-mile long Overseas Highway that's an experience in itself. Most sailing charter visitors arrive by air and take the short transfer to one of the charter bases located on the island. Famous for its coral reefs, local architecture, historic sites and nightlife, charming Key West is well worth some time before or after your charter.  

Like most charterers however, you will probably be keen to go sailing and start exploring the chain of cays that make up this most southerly part of the Continental USA. Two great things about sailing here are that distances between attractions can be as short as you'd like them to be, and anchorages are plentiful, if shallow in places. A seven-day charter Key West to Key Largo and return is easily achievable. 

Travelling out of the Stock island marina, it's less than 30 nautical miles to Baihia Honda Key, a popular stopover. In the vicinity there's a variety of stunning beaches, some say the best in the world. Looe Key has some of the best snorkelling you'll experience on your vacation. 

A similar distance to that travelled above will take you from Bahia Honda Key to Long Key, via Marathon, a major sport fishing town of 10,000 people surrounded by the bountiful sea. Stop a while and enjoy a seafood lunch, or you may prefer to do Marathon on the return. At Long Key enjoy the natural surroundings, the greenery and the birdlife. 

Perhaps after two days of sailing that have taken you from Key West more than half way to the mainland, you're ready to take it a bit easier. Less than ten nautical miles onward you'll come to Indian Key Historic State Park at Islamorada. Nearby is the San Pedro Underwater Archeological Preserve, another one of the numerous state parks along the Keys. The San Pedro was a Dutch ship sunk during a hurricane in 1733. What remains lies in 18 feet of water 1.25nm south of Indian Key, easily accessible to good swimmers. 

From Indian Key, it's a further 20nm sailing distance to Key Largo. Apart from the shops, bars and restaurants, most of the attractions are aquatic-based as they are all along the Keys. A visit to the Florida Keys Wild Bird Rehabilitation Center can be rewarding, a reminder of the fragility of nature in this delicate place. 

If you enjoy walking while on vacation, the Florida Keys Overseas Heritage Trail is accessible to many points along your sailing route. 

Browse our yachts for charter in Florida Keys

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  • Matching any competitive offer
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  • We do more than just book yachts!

We will match any discount website offer on charter boat price, and still provide our customary high level of service.

The Essential Guide to Sailing Holiday Charters

The Sail Connections Essential Guide to Bareboat and Crewed Sailing Holiday Charters is jam-packed full of useful tips for getting the most out of your next boat charter. And it is FREE to download.

Enquire about a charter...

For a personal proposal structured to meet your needs, with advice on all aspects of your sailing charter.

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Bareboat Charter

A bareboat charter means the charterer, as Captain, is solely responsible for the safe operation of the vessel, including all aspects of navigation, anchoring, docking, and controlling the vessel under sail or power. Key West is considered an advanced sailing destination and for the safety of other passengers and the vessel, it is vital the charterer have sufficient experience aboard vessels of a similar size & type as what you are seeking to hire. We also require there be one other person aboard to act as first mate, with enough boating experience to handle the vessel in the event the Captain is injured or goes overboard.

All of our bareboat charters have a 5 day/4 night minimum which is the ideal amount of time to experience one of our Florida Keys sailing itineraries .

Am I qualified?

Sail with confidence, am i qualified for bareboat charter.

The Florida Keys is considered an advanced sailing destination, offering great natural beauty in sometimes rare peaceful isolation. There are almost exclusively anchorages in our cruising grounds subject to tidal changes and currents, including open anchorages in the Westerly Island groups.

Our bareboat charter application will help us evaluate your sailing experience to establish your skill level, and that of your first mate, as suitable to these conditions. This application should be filled out in full, providing as much information as possible to validate your skills and experience. Please submit the requested documents together in order to complete the application process. No booking should be considered confirmed until this application has been approved by the reviewing Charter Base Manager. You may be contacted directly to answer any questions they may have.

Bareboat Charter General Qualifications & Requirements

•30 days or 400 miles in the last three years as named Captain on an equivalent size & type of yacht(s).

•ASA, US Sail, RYA or ICC certification to an equivalent Bareboat Charter level for Monohull & Multi Hull for Catamaran.

•Physically capable of handling the vessel in all situations & conditions (i.e. Managing sails, lines & anchor).

•Must have a qualified First Mate who completes a Crew Resume for approval.

•Must present a valid US driver’s license, or International Passport to verify identity and DOB.

•We reserve the right to approve your application on the condition of having a Check-Out Captain aboard for the first day (or more) at your expense, which would be agreed to in advance as a condition of approval.

•For applicants under the age of 30 or over 74 additional crew requirements may apply.

Don’t be discouraged if your experience isn’t quite strong enough yet. We offer several ways to assist charterers to meet the requirements. As well as being able to offer an ASA instructor accompany you on your bareboat charter so you can achieve your ASA Sailing Certifications , we can also arrange a one or two day refresher for an experienced mariner that might need to get familiar with some of the more advanced systems on newer boats, or just brush up on skills if it’s been awhile. These programs are very flexible and can be personalized to each charter guest.

Download our Captains Application: Captains Application for Sailing Vessels

First Mate’s Application for Sailing Vessels

For Power Vessels

During the charter check-in process, which takes approximately 2½ hours, you will receive a very comprehensive yacht systems orientation, inventory review, safety briefing, and a chart briefing of the cruising area to ensure you are comfortable with your float plan and the vessel. It is required that the Captain & First Mate arrive at the same time and attend the vessel check -in.

Optional Orientation cruise If you are chartering a manufacturer of boat for the first time and would like to do a short orientation sail to familiarize yourself with all the systems and equipment while under way, we highly recommend an orientation sail with a Captain familiar with your sailing vessel. It takes about an hour and they charge $150.00. This is an excellent way to do a shake down sail to make sure you can enjoy your vessel with confidence. This must be booked in advance to ensure there is a Captain available. This is not intended to teach boat handling skills.

6651 Maloney Ave, Unit 1 Key West, FL 33040

[email protected] 800-650-6940

KEEP IN TOUCH

Destination and charter fleet updates, special offers, and more

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The Florida Keys

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Featured Yachts in Florida Keys

Sovereign Main

Sovereign | From US$ 45,000/wk

Latest florida keys yachting news.

Horizon Yacht launches 34m motor yacht CROWNED EAGLE – the fifth FD110

Horizon Yacht launches 34m motor yacht ...

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Florida Keys Yacht Charter

Often considered America 's Caribbean Islands the Florida Keys yacht charter offers spectacular locations to explore.

You will often read references to a 'jade necklace' or a 'string of pearls' in descriptions of the many (800+) islands that stretch off into the sea. The Keys have become increasingly busy over the last few years with an increase in cruise ship and other tourism. The keys feature plenty of energy ashore, but to get away into the quieter areas a charter yacht is the only way to go.

florida keys rental with sailboat

Photos: 1. A diver explores the coral reef in the Florida Keys National Marine Sanctuary off Key Largo - The reef system in the Keys is the only contiguous coral barrier reef in North America - Photo by Bob Care-Florida Keys News Bureau; 2. A Florida Keys fishing guide positions his angler to cast for a bonefish off Key Largo- Photo by Bob Krist-Florida Keys News Bureau; 3. Sunset in Key Largo- Florida Keys- paints a pretty picture at the Kona Kai Resort -Photo by Bob Krist-Florida Keys News Bureau

The first Key to come across on your cruise south will be Key Largo . Over the years Key Largo has become a busy weekender retreat from the mainland. As you sail further down though the Keys you will finally come to the last one, Key West .

The Florida Keys are sheltered by the only living coral reef in the United States. The Keys are well known to yacht charterers for the spectacular scuba diving and snorkelling, kayaking and eco-tours, dolphin watching, island hoping and fishing.

The types of yacht charter available in the Florida Keys are all the main types including motor, sailing, bareboat charter, skippered, crewed yachts, catamaran, power boat, sailboat, luxury yachts and super yacht charter.

The Florida Keys features a year round calendar of special events such as fishing tournaments, international yacht races, motor yacht races, Fantasy Fest, a lighted boat parade and Florida's own 10 day long Mardi Gras. We recommend charter yachts with a draft of under 4 or 5 ft (1.3 - 1.5m), as with a catamaran, so that you can get in to all the best areas within the Florida Keys.

Key West Yacht Charter

Key West has the ideal year round climate for yacht charter. Key West is a very unique town being the southernmost US city where history and tradition meets natural beauty and serenity. This city has real estate titles that date back to the King of Spain! Within walking distance from the historic Seaport District you will find palm-lined streets, tropical gardens, Ernest Hemingway's home, fine shops, art galleries, quaint restaurants and cafes. You can walk in the footsteps of Thomas Edison, Lou Gehrig, Harry Truman, and Tennessee Williams. You will also discover lively bars and pubs along with street musicians, jugglers, mimes and artists.

It is not unusual for charter guests to day sail their charter yachts using Key West as a base. They will sail and explore the keys during the day, utilising the restful anchorages, and then return to the first class marinas at night to experience Key West's nighttime entertainment. Remember to radio ahead to reserve marina space, as Key West is a busy part of the Florida Keys.

Below is a selection of fabulous Florida Keys charter yachts - please, contact us for additional vessels and more information here .

  • Florida Keys Charter Itinerary
  • Browse Florida Keys Charter Yachts
  • Luxury Motor Yachts for Charter in Florida Keys
  • Luxury Sailing Yachts for Charter in Florida Keys
  • Luxury Catamarans for Charter in Florida Keys
  • Florida Keys Yacht News

Florida Keys Yacht Charter Enquiry

"I have just emailed your post charter feedback to you. It doesn't say nearly enough about how well and hard you worked on this deal. I am a retired commercial real estate broker who understands the importance of the deal-maker in the deal. You are a deal maker of the first order." E. G - chartered in Florida Keys.

Yachting Destinations Near the Florida Keys

In close proximity to the Florida Keys are a number of exciting sailing destination.

Delta Pacific Northwest

New England

New England Lighthouse In Late Afternoon The Portland Head Light At Portland Maine USA

Napa Valley

Yachts for charter in the florida keys, queen miri | from eur€ 1,125,000/wk.

Exterior

KENSHO | From EUR€ 850,000/wk

Luxury Superyacht KENSHO By Admiral Yachts

WAYFINDER | From EUR€ 375,000/wk

Yacht Support Vessel WAYFINDER Cruising With Tenders

STARSHIP 185' | From US$ 275,000/wk

Luxury Yacht STARSHIP 185 With A Slide

MARIA | From US$ 230,000/wk

The 52m Yacht MARIA

LADY ELAINE | From US$ 225,000/wk

Exterior - Main

GIGI | From US$ 225,000/wk

The 49m Yacht HARMONY

TCB | From US$ 215,000/wk

Luxury Superyacht TCB

MYSORAH | From US$ 200,000/wk

MYSORAH (ex Major Wager)

ASPEN ALTERNATIVE | From US$ 199,000/wk

Motor Yacht Aspen Alternative

FAM | From US$ 195,000/wk

Forward: Yacht FAM's Cruising Captured

GLORY | From US$ 179,000/wk

Luxury yacht AKULA

ZOOM ZOOM ZOOM | From US$ 175,000/wk

Running

AVALON | From US$ 155,000/wk

Running Shot

FOCUS | From US$ 150,000/wk

Yacht FOCUS - Profile Underway

AQUASITION | From US$ 150,000/wk

Profile Aspect Aboard Yacht BIG ZIP

RELENTLESS | From US$ 150,000/wk

Exterior

PERSISTENCE | From US$ 140,000/wk

Superyacht PERSISTENCE

ANTELOPE IV | From US$ 140,000/wk

Motor yacht Elsea - an example of Italyachts 43m superyacht

CLAIRE | From US$ 139,500/wk

Forward Aspect On Yacht CLAIRE

Florida Yacht News

Luxury yacht INVICTUS available for charter in select destinations in the USA and Bahamas

Luxury yacht INVICTUS available for ...

Florida charter yacht REAL SUMMERTIME offering 10% discount

Florida charter yacht REAL SUMMERTIME ...

38m superyacht GLORY offering charters around Florida and the glorious Bahamas

38m superyacht GLORY offering charters ...

Remodelled superyacht PERSISTENCE offered for charter in Florida

Remodelled superyacht PERSISTENCE ...

Charter yacht disclaimer.

This document is not contractual. The yacht charters and their particulars displayed in the results above are displayed in good faith and whilst believed to be correct are not guaranteed. CharterWorld Limited does not warrant or assume any legal liability or responsibility for the accuracy, completeness, or usefulness of any information and/or images displayed. All information is subject to change without notice and is without warrantee. A professional CharterWorld yacht charter consultant will discuss each charter during your charter selection process. Starting prices are shown in a range of currencies for a one-week charter, unless otherwise marked. Exact pricing and other details will be confirmed on the particular charter contract. Just follow the "reserve this yacht charter" link for your chosen yacht charter or contact us and someone from the CharterWorld team will be in touch shortly.

Captain Hook's | Serving Marathon, Big Pine Key and Key West

Florida Keys Boat Rentals

Marathon  boat rentals.

Fun and Reliable Rental Boats in Marathon with Keyzboats Boat Rentals!

If you want to be a captain for the day or a week, our Florida Keys boat rentals are just what you need! Pilot your own rental boats throughout the Marathon waters. Enjoy fishing, snorkeling, diving, and sightseeing all within the privacy of your own rental. You can discover your own secret fishing spots, dive and snorkel the beautiful reefs, or just soak up the sun at the sandbar. KeyzBoats employees can give you some insight on the new hot spots whether you are looking for that trophy fish or just to catch some rays! All of their rental boats meet the approved Coast Guard safety equipment requirements, are fuel efficient and well maintained. Call today and be captain for a day (or more!).

florida keys boat rentals, marathon key boat rentals, boat rentals marathon

Rental Boat FAQ

Are we free to travel anywhere.

Yes! KeyzBoats may have a distance from Capt. Hook’s restriction with your rental boats.  Please check with them before you decide to go long distances with your rental. KeyzBoats will advise you on the shallow areas when you pick your rental. It’s always important to watch the water closely in the shallow areas and look for markers that indicate safe depths.

Are your rental boats equipped for fishing?

Yes, KeyzBoats have several boats equipped for fishing including outriggers, livewells and plenty of storage for your future dinner.

Can we use the boat at night?

No, KeyzBoats do not come with the lights required for night time operation. 

How many passengers can I bring?

Each boat is rated for a different number of riders. It depends on the size of the boat. We have varying sizes up to 12 passengers. Deck boats, in general, are rated for more passengers.

Great Experience

"My husband and I had a great time snorkeling with Captain Hooks! Our crew took the time to explain everything, brought us to a great spot, and we got to see an iconic corral! It was our 1st time snorkeling and it was such a great experience we will definitely do it again!"

Friendly Crew

"Great excursion to two reefs under the directions of Captain Dave. Boat holds about thirty people of teams of about five to six divers or snorkelers with a Diver Master who is very attentive. The boat also has a very outgoing and friendly crew. Experience a four hour tour that passes by too quickly due to the fun. Please don't forget to bring tips for the Diver Masters and the crew."

Great Snorkeling Trip

"Great snorkeling trip and brochure perfect day in Marathon. Captain Mike, David & Kevin did a great job. Recommended for everyone."

Middle Keys Rental Boats

Affordable, Fun for Fishing, Snorkeling, Diving & Sightseeing, Rent a Boat Here in the Middle Keys

There’s a new boat rental business in town – KeyzBoats – and they do an awesome job! We have been working with them for about a year now and they have been super.  Click the button below to check out their business and their available rental boats.

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(305) 684-9031

Reef Marine Logo

Boat Charters, Fishing Rentals, & Snorkel Tours

Established in 1989, Reef Marine Inc. is proud to call Islamorada home. We know the Florida Keys like no one else, and our wide array of watersports rentals and boat tours keep our satisfied customers coming back to us time after time again. Our low prices may get us noticed, but we’re just as proud of our superior service. Contact us at (305) 684-9031 today to  request a reservation for your next aquatic adventure.

Boat Rentals

Boat Rentals

Snorkeling

Fishing Charters

Boat Tours

Ready for a New Adventure?

Excitement awaits in the famous waters from Key Largo to Islamorada and beyond. Explore miles of pristine coastline, gorgeous beaches, turquoise waters, and coral reefs as you cruise along with Reef Marine.

Family-Fun Boat Rentals

If you'd rather be at the wheel during your aquatic adventures, we also have boats for rent by the hour, day, or week. Whether you're hitting your secret fishing hole with some buddies or taking the family out for a relaxing day on the water, we've got you covered. All our vessels are pet friendly, so bring Fido along, and rest assured that you'll find everything you need on board.

Snorkeling Tours

Snorkeling Tours

Want to jump right into the water and explore the coral reefs? Join one of our snorkeling tours , and our experienced guides will take you to some of the most beautiful locations along the coastline. Visitors typically see plenty of fish, beautiful corals, and may even encounter dolphins, turtles, and manatees while swimming along the reef.

Boat Charters & Tours

Since many anglers flock to the Florida Keys to experience world-class fishing, some of our most popular boat charters are fishing trips. But there are other options too, including eco tours and sunset cruises. And best of all, everything can be customized to suit your needs. Come aboard and see why we love living in the Keys.

Whatever activity you choose for your time in the Florida Keys, we’d love to help you create lasting memories! Take a look at our current specials , and then call Reef Marine at (305) 684-9031 to request a reservation

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TROPICAL BOAT RENTALS

305-481-7006

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RESERVE YOUR BOAT!

florida keys rental with sailboat

25' Sea Chaser

florida keys rental with sailboat

26' Sea Hunt

florida keys rental with sailboat

27' Sea Chaser

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32' Glasstream

florida keys rental with sailboat

30' Pro-Line

florida keys rental with sailboat

33' HydraSport

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34' HydraSport

florida keys rental with sailboat

WHY BOOK WITH TROPICAL?

We pride ourselves in offering professional and quality service since 2007 and look

forward to  welcoming you onto our boats.  Our fleet of rental boats are well maintained,

equipped (Coast Guard approved)  and ready for you to take out for great boating fun

in the beautiful waters of the Florida Keys.   Please contact us to make your boat rental

arrangements.  If your Florida Keys accommodation does  not have dockage, no problem,

you'll be able to use our dock at Tropical Boat Rentals that is centrally  located in Marathon,

Florida.  We are very organized and have excellent customer service.  We utilize our slow

season to do body work on the boats, to keep them in great shape and keep them updated

to make sure that our customers receive top of the line boats.

Our entire Fl Keys rental boats are deep V-Offshore T-top boats with Four Stroke Yamaha motors, GPS, depth finders, and outriggers. Take a week-long fishing trip of a lifetime in our world-famous Florida Keys and Key West waters or just enjoy a day of cruising and a picture-perfect sunset with your family. The choice is yours…we’re just here to help make your vacation dreams come true!

We are proud of our attention to detail by providing a quality boat rental for our Florida Keys and Key West customers. We are always available for answers to your questions or if you have some type of problem and need assistance, we are a phone call away! So, please accept our personal invitation to make the most out of your Florida Keys and Key West vacation by renting one of our top-of-the line boats.

Our living coral reef has so much to see while you snorkel or scuba dive from one of our rental boats. Our Fl Keys boat rentals are able to take you to the reef, they are ocean going boats. Many coral reef patches can be found off the Florida Keys – Molasses Reef, Hen and Chickens, Tennessee Light, Sombrero Light. Also, scuba dive destination dives – Spiegel Grove wreck, USCG Duane & USCG Bibb, The Eagle, and many more. We meticulously inspect each Fl Keys rental boat before it leaves our dock with a long check list. We also make sure you are comfortable in your rental boat by showing you how to use all the equipment. We are happy to take you out for a spin on your choice of Fl Keys rental boat to show you just how comfortable our boats are!

florida keys rental with sailboat

WHAT DO PEOPLE THINK OF US?

The boat was great and the Yamaha 4-stroke really put it over the top. We fished all day and could go wherever we wanted. I will definitely be back to rent again and I will tell all my friends about Tropical Boat Rentals, you’re the best.

“ Mr. Fassett, I wanted to write and thank you for your fine service this summer. My family, along with several friends and their families rented two boats from Tropical in June and your service and boats were superb. You and your boats were where they were supposed to be when they were supposed to be. And the boats worked and ran flawlessly! I have never had a rental boat experience in the Keys that came close to what you provided. Thanks for doing your part to make our vacation terrific!! “

CALL US (8am - 7pm EST)

91 Ave A, Marathon, FL 33050

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Rent the best Florida Keys yachts

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How to rent a yacht in florida keys, find the perfect boat.

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Why Boatsetter?

As the global leader in peer-to-peer boat rentals, Boatsetter offers an easy, safe and accessible way to experience on-the-water adventure. With boat rentals in 600+ locations, finding a boat is easy and with the option to tap into the largest network of USCG licensed captains, boating experience is not required.

Boating with Boatsetter

Get out on the water worry-free, knowing our insurance covers every boating trip

Choosing the right boat rental platform is essential to your peace of mind while on the water. That's why we've gone the extra mile to focus on safety through our exclusive partnership with GEICO Marine and BoatUS. As the first and only boat rental marketplace to offer insurance on every peer-to-peer rental, you are protected during all rentals with insurance coverage and on-water assistance through TowBoatUS.

Got questions?

Frequently asked questions

What makes Boatsetter different from other boat rental platforms?

What makes Boatsetter different is peace of mind. Boatsetter is the first and only boat rental marketplace to offer insurance on every peer-to-peer boat rental. We know choosing the right boat rental platform is essential to your experience while on the water. That's why we've gone the extra mile to focus on safety through our exclusive partnership with GEICO Marine and BoatUS. As the first and only boat rental marketplace to offer insurance on every peer-to-peer rental, you are protected during all rentals with insurance coverage and on-water assistance through TowBoatUS.

How to rent a boat on Boatsetter?

At Boatsetter, our mission is to make getting out on the water as easy as possible. With our intuitive booking system, you can rent a boat as soon as today. -First, you must determine your budget and the type of boat you want to rent. -Next, decide where you would like to boat and the kind of boat you would like to spend the day on. -Finally, determine if you will be needing a boat captain and reach out to the boat owner. That’s it! You’re officially on your way to a fantastic day out on the water.

How much does it cost to rent a boat?

The cost to rent a boat depends on whether you are renting for a half-day or a full day, the boat features and the boat size can impact your boat rental price. Rental prices can range from $200 to $1,000 plus depending on the boat rental itself and the length of time of the rental.

How many people can fit on the boat rental?

The number of people who can fit on boat rental largely depends on the boat’s size and how many life jackets are on board. Currently the coast guard allows a maximum of 10-12 people on a Boatsetter boat rental.

How much does it cost to rent a yacht?

The cost of renting a yacht depends on the boat’s size and the amount of time you’ll use the yacht. The onboard amenities and luxurious accommodations also dictate the price. You can contact our yacht specialists for a custom quote by visiting https://www.boatsetter.com/luxury-yacht-charters .

How old do you have to be to rent a boat?

You must be 18 years old to rent a captained boat and 25 years old if you would like to rent a bareboat charter.

Do I need a boating license to rent a boat?

Boating license requirements vary from state to state. As a renter, you are responsible for understanding local state requirements.

Can you rent a yacht for the day?

Boatsetter allows you to rent a yacht for the day. Single-day yacht rentals are available for a select number of yachts. To chat with a yacht specialist please visit https://www.boatsetter.com/luxury-yacht-charters .

Can you rent a yacht for the week?

Boatsetter allows its customers to rent a yacht for the week. Renting a yacht for a week gives you more access to the wide range of yachts available on our platform. You can either book a rental directly through the site or connect with one of our charter specialists to plan your trip here: https://www.boatsetter.com/luxury-yacht-charters .

Can you rent a yacht for the month?

Booking a month-long yacht rental is a detailed and hands-off process when working with our team of yacht charter specialists. We tailor each yacht charter to our client's specific wants and needs. Our luxury yacht charter specialists can be reached at (954) 715-4114 or by visiting https://www.boatsetter.com/luxury-yacht-charters .

How to rent a private yacht?

Renting a private yacht is a very detailed experience that caters to your exact needs while onboard one of our luxury yachts. To plan your private yacht rentals experience please visit https://www.boatsetter.com/luxury-yacht-charters .

How much does it cost to rent a pontoon boat?

The cost of renting a pontoon boat depends on the size, location, and rental time of the boat. Prices can range anywhere from $200 for a half-day rental or just under a $1,000 for longer rentals.

How much does it cost to charter a yacht?

The cost to charter a yacht varies depending on the boat size and the length of the charter. Prices typically range from less than $1,000 to $5,000 plus if you’re wanting to charter the yacht overnight.

How much does it cost to rent a boat for the day?

The cost of renting a boat for the day on average ranges from $200 to $1200. The cost to rent a boat varies depending on the size of the boat and the length of time that you will be using the boat.

How does the boat insurance work?

Boat insurance typically covers loss caused by things such as fire, sinking, storms, and collisions. The extent of the coverage varies depending on the policy.

Do I need my own insurance to rent a boat?

You do not need boat insurance when renting with Boatsetter. Coverage is provided under the Peer-to-Peer Boat Rental Policy, which is underwritten by GEICO Marine Insurance Company. The policy was written from the ground up as a stand-alone recreational boat rental insurance policy covering the period of time that the boat is being rented and is available for all non-commercially insured boats.

Does Boatsetter screen renters?

Yes. We use a system called Cognito to ensure that payment information matches the renter's identity. We also require renters taking out a captained boat to be at least 18 years old and on a bareboat to be at least 25 years old.

Is listing my boat on Boatsetter free?

Yes! Listing a boat is completely free. We only take a commission when your boat is rented. We only make money when you do!

What if I'm not comfortable having a renter drive my boat?

If you are not comfortable having a renter drive your boat, we have an expansive network of licensed and experienced captains. Once your boat is listed, you can filter through our network of captains and favorite captains in your area that you would like to operate your boat.

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Miami

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TOP BOAT!...

Great experience on JetSet! great boat and great crew! would definitely recommend!

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We had a really great experience on David's boat. The captain and crew (Lester and Marie) we really nice and...

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Went out on David's boat for the second time. And once again it was an all around great experience! Captain Lester...

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Best captain and co host. Very friendly. Kept the boat clean and travel was very smooth. Highly suggest. GREAT SERVICE

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Had such a fun time! Everyone was great and Yani makes amazing drinks!

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My second time renting this boat, and smooth sailing yet again! Always clean, hospitable, and easy pick up location.

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Boat vacation rentals in Florida Keys

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Top-rated boat rentals in Florida Keys

Guests agree: these boat rentals are highly rated for location, cleanliness, and more.

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Boat in Tavernier

Island Sanctuary Islamorada

Stay aboard the eco-friendly two-story 63 ft River Queen with a 360 degree view with beautiful sunrises and sets, mored 1/8 mi offshore in a quite harbor close to shopping center, movie theater, hospital, bars & restaurants. A 10-foot dinghy with small outboard to come & go from shore "ONLY", nowhere else. I also offer Personal Training, deep tissue work & Life Coach sessions. I live on the vessel about a hundred yards from you so if there are any questions, etc. I will be there to assist you.

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Home in Miami

Luxury Home in Brickell Miami, 5 min to the Beach!

This amazing home situated in a convenient location of Miami, was professionally designed and accommodated to suit your vacation needs. Enjoy our chef inspired large fully equipped kitchen, our ample sophisticated and modern bathrooms, as well as our comfortable bedrooms, upgraded with fine linens and hotel quality mattresses. The Roads is an incredible neighborhood in the limits of Brickell, filled with sidewalks, roundabouts, wide tree lined streets surrounded by tropical native Miami plants.

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Condo in Miami

The Love Lounge Miami Beach & its 420 Friendly

READ THE REVIEWS to see how much of an effort we make to ensure you have the BEST TIME while here. This place is in SOUTH BEACH MIAMI not the venetian causeway. The place has 2 TVs, 2 Queen beds. Prime Location 💯. NO CIGARETTE SMOKING, NO ANIMALS ALLOWED & NO SHOES INSIDE. Keep in mind that other people live within the building, so be aware of the noise but HAVE FUN. This is not a hotel; this is an Air bnb. You will NOT find a better deal on MIAMI BEACH in this area with a host like Vincent.

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Boat in Key West

Amazing 4 Bdrm, 4 Bath Catamaran - Purpus

Enjoy all the comforts of home including 4 luxurious staterooms with queen sized beds each with its own private bathroom, a full kitchen with everything needed for on board meal prep, spacious living areas down below and above on the decks. The boat is in great condition and has been well maintained inside and out. Purpus is docked in a first class marina with access to free parking, restaurants, bars, ships store, pools, coffee shop and laundry. Charter options available for additional fee.

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Boat in Fort Lauderdale

Graceland Las Olas Boathouse Treehouse by Beach

A short walk to the beach and downtown, Graceland is where your boat house becomes a tree house on a high tide. This 1979 remodeled vintage double cabin is a hidden gem, an exotic experience for the most sophisticated travelers. Situated conveniently on Las Olas, Grace (formerly Athena) is a short walking distance to the bustling downtown & the sunny beaches of Fort Lauderdale. The boat has 2.5 cabins & 2 full en-suite bathrooms with salt water heads. Host lives onsite and available as needed.

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Make Memories and Enjoy Sunsets on Euphoria

PLEASE READ ALL THE SECTIONS IN THE LISTING. 31ft BOAT ANCHORED at 1.5 mile off Key West NOT IN A MARINA. Transportation to the boat by water shuttle, fee not included in stay. REMEMBER ITS A BOAT, FUN EXCITING, ACCEPTANCE OF TRANSIENCE AND IMPERFECTIONS. THE AESTHETIC IS SOMETIMES DESCRIBED AS ONE OF APPRECIATING BEAUTY THAT IS IMPERFECT, IMPERMANENT AND INCOMPLETE IN NATURE. Embracing simplicity, nature imperfection and find joy, peace that nothing is perfect in this world. Enjoy Life

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Boat in Key Largo

Yacht/Catamaran ON THE WATER in a Key Largo marina

You Must contact us before booking, the boat is often booked far in advance with multi-day sailing trips which do not reflect on this calendar. Enjoy a unique vacation experience on our comfy sailing catamaran, docked, inside a small Key Largo marina. 3 full suites with bathrooms means 6 people comfortably sleep. This listing is for the catamaran INSIDE the marina, for sail trips, message us! Ask us about our TripAd\/is0r reviews too! Our guests always love their sailing adventures!

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ALL INCLUSIVE! Snorkel/Sail/Spear Fish/Fishing/Fun

You will love staying on this 45' GulfStar Sloop. The boat boasts 2 BR, 1.5 bath with shower, full working galley, A/C throughout and plenty of room to relax down below. Every reservation comes with a sunset sail along with day sailing, snorkeling or fishing. Layout and be lazy on the spacious deck or whatever you would like to do! Visit SailAway GetAways on FB for more detailed view. **Unfortunately one night reservations do not allow time for excursions. Except a sunset sail.**

florida keys rental with sailboat

Boat in Islamorada

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

florida keys rental with sailboat

Last Minute Discount! 48' Yacht & Beautiful Resort

Enjoy exclusive use of this 48-foot yacht all to yourselves, with the opportunity to get close to ocean life. This yacht is docked at the Perry Hotel & Marina, with free access to two stunning waterfront swimming pools, live music, three restaurants, complimentary shuttle service, & more. Come and go on the yacht anytime, day or night. Participating in an ocean excursion on this yacht is mandatory & comes at an extra charge. Inquire here about our other yachts in our fleet

florida keys rental with sailboat

Boat in Miami

Sailboat with a view

EnjoyScenics views of downtown Miami and the entry port.On the other side the islands that connect it to Miami beach. The boat is on a mooring, with unique 360 degrees view. At same time require to go from shore with a dinghy .we provide the service. We include 1 roundtrip per day then it's $10 per roundtrip . Regular hours it's from 730 am till midnight. We have some exceptions for after hours with previous arrangements and during the ultra festival till 3am.

florida keys rental with sailboat

Townhouse in Key Largo

Beautiful Oceanside Mariner's 3 Bedroom Townhome

This marina facing 3 bedroom townhome is spacious and beautifully decorated. Relax with the whole family at this peaceful place to stay. The Oasis pool is probably the nicest pool in Key Largo with Ocean views and beach entrance it is a great spot for any age. Boater's would love this very well maintained Marina. Tennis and Pickle ball on site. Game room for kids and adults to enjoy. Many restaurants, watersports, and excursions nearby.

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Today Is The O'Day!

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Luxury Living on the Water

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Island Life Boat Rentals

Photo of Island Life Boat Rentals - Cedar Key, FL, US. 18' Pontoon boat with livewell

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Cedar Key Marina

Cedar Key, FL 32625

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Pontoon Boat Rentals for the avid fisherman or just to cruise around the islands! …

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Your Guide to a Florida Keys Road Trip: Key Largo to Key West

Posted: March 12, 2024 | Last updated: March 13, 2024

<p>One of the <a href="https://www.rd.com/list/best-states-road-trip/" rel="noopener noreferrer">best state road trips</a> in America has to be the sun-kissed drive from Key Largo to Key West in the Florida Keys. This road, known as the Florida Keys Overseas Highway, takes you through a 125-mile island chain that begins just south of Miami. It hopscotches over 42 bridges and five islands, and has turquoise waters stretching in every direction into the Atlantic Ocean, Florida Bay and Gulf of Mexico.</p> <p>So if you're looking for the perfect <a href="https://www.rd.com/article/atlantic-coast-road-trip/" rel="noopener noreferrer">Atlantic Coast road trip</a> or <a href="https://www.rd.com/list/best-budget-friendly-beach-destinations/" rel="noopener noreferrer">cheap beach vacation</a>, look no further than this <a href="https://www.rd.com/article/the-ultimate-american-road-trip-guide/" rel="noopener noreferrer">road trip guide</a> from Key Largo to Key West. And if you'd rather travel from Key West to Key Largo, rest easy—the route works either way. There are shuttles that run from Key Largo to Key West, but keep in mind, you'd be missing out on all the fun in between.</p> <p>By the way, once you embark on the Florida Keys Overseas Highway, you'll notice that many sites along the way use mile markers (MM) in their address. We use those mile marker points in this story to help you navigate the drive.</p> <p><strong>Get <em>Reader's <b><i>Digest</i></b></em><b>’s</b> </strong><a href="https://www.rd.com/newsletter/?int_source=direct&int_medium=rd.com&int_campaign=nlrda_20221001_topperformingcontentnlsignup&int_placement=incontent" rel="noopener noreferrer"><strong>Read Up newsletter</strong></a><strong> for more travel, humor, cleaning, tech and fun facts all week long.</strong></p>

Your road trip guide to the Florida Keys

One of the best state road trips in America has to be the sun-kissed drive from Key Largo to Key West in the Florida Keys. This road, known as the Florida Keys Overseas Highway, takes you through a 125-mile island chain that begins just south of Miami. It hopscotches over 42 bridges and five islands, and has turquoise waters stretching in every direction into the Atlantic Ocean, Florida Bay and Gulf of Mexico.

So if you're looking for the perfect Atlantic Coast road trip or cheap beach vacation , look no further than this road trip guide from Key Largo to Key West. And if you'd rather travel from Key West to Key Largo, rest easy—the route works either way. There are shuttles that run from Key Largo to Key West, but keep in mind, you'd be missing out on all the fun in between.

By the way, once you embark on the Florida Keys Overseas Highway, you'll notice that many sites along the way use mile markers (MM) in their address. We use those mile marker points in this story to help you navigate the drive.

Get Reader's Digest ’s   Read Up newsletter for more travel, humor, cleaning, tech and fun facts all week long.

<p><strong>Mile marker:</strong> 108–90</p> <p>The first of the Florida Keys you'll hit after driving about an hour south from Miami en route from Key Largo to Key West is, well, Key Largo. Often referred to as the Dive Capital of the World, Key Largo includes one must-see stop: John Pennekamp Coral Reef State Park (MM 102.5), the first underwater preserve in the United States.</p> <p>Experienced and novice snorkelers and SCUBA divers will be enthralled by the teeming marine life that lives just below the water's surface, like parrot fish, barracudas and sea turtles. More experienced divers enjoy exploring the USS Spiegel Grove, one of the largest ships ever intentionally sunk to create an artificial reef where pretty fish can thrive.</p> <p>Back on dry land, travelers can wander nearly six miles of trails at Dagny Johnson Key Largo Hammock Botanical State Park, home to more than 80 species of plants and animals. You can also peruse the work of local artists at myriad galleries.</p> <p><strong>Best beach:</strong> Cannon Beach, found within John Pennekamp Coral Reef State Park, has shallow waters that are perfect for wading. You may even spot cannons and anchors on the beach that remain from a 1715 Spanish shipwreck.</p> <p><strong>Where to eat: </strong>Dig into the catch of the day at The Fish House, Key Largo Conch House or Snook's Bayside Restaurant & Grand Tiki Bar, some of the best <a href="https://www.rd.com/list/traditional-restaurant/">traditional restaurants</a> in the area. If you'd rather turf than surf, check out Jimmy Johnson's Big Chill.</p> <p><strong>Where to stay:</strong> If you can't get enough of the underwater world, stay at <a href="https://www.tripadvisor.com/Hotel_Review-g34344-d218568-Reviews-Jules_Undersea_Lodge-Key_Largo_Florida_Keys_Florida.html" rel="noopener noreferrer">Jules' Undersea Lodge</a>, the world's first underwater hotel. If you'd rather keep dry, try the adults-only <a href="https://www.tripadvisor.com/Hotel_Review-g34344-d13980722-Reviews-Bungalows_Key_Largo-Key_Largo_Florida_Keys_Florida.html" rel="noopener">Bungalows Key Largo</a>.</p> <p class="listicle-page__cta-button-shop"><a class="shop-btn" href="https://www.tripadvisor.com/Hotel_Review-g34344-d218568-Reviews-Jules_Undersea_Lodge-Key_Largo_Florida_Keys_Florida.html">Book Now</a></p>

Mile marker: 108–90

The first of the Florida Keys you'll hit after driving about an hour south from Miami en route from Key Largo to Key West is, well, Key Largo. Often referred to as the Dive Capital of the World, Key Largo includes one must-see stop: John Pennekamp Coral Reef State Park (MM 102.5), the first underwater preserve in the United States.

Experienced and novice snorkelers and SCUBA divers will be enthralled by the teeming marine life that lives just below the water's surface, like parrot fish, barracudas and sea turtles. More experienced divers enjoy exploring the USS Spiegel Grove, one of the largest ships ever intentionally sunk to create an artificial reef where pretty fish can thrive.

Back on dry land, travelers can wander nearly six miles of trails at Dagny Johnson Key Largo Hammock Botanical State Park, home to more than 80 species of plants and animals. You can also peruse the work of local artists at myriad galleries.

Best beach: Cannon Beach, found within John Pennekamp Coral Reef State Park, has shallow waters that are perfect for wading. You may even spot cannons and anchors on the beach that remain from a 1715 Spanish shipwreck.

Where to eat: Dig into the catch of the day at The Fish House, Key Largo Conch House or Snook's Bayside Restaurant & Grand Tiki Bar, some of the best traditional restaurants in the area. If you'd rather turf than surf, check out Jimmy Johnson's Big Chill.

Where to stay: If you can't get enough of the underwater world, stay at Jules' Undersea Lodge , the world's first underwater hotel. If you'd rather keep dry, try the adults-only Bungalows Key Largo .

<p><strong>Mile marker:</strong> 90–63</p> <p>Next up en route from Key Largo to Key West is the fisherman's paradise known as Islamorada. Considered the Sport Fishing Capital of the World, it's where backcountry sport fishing and saltwater fly-fishing got their start. Countless seasoned boat captains are ready for hire to take you out to catch the wahoo, marlin, mahi-mahi and tuna that swim in these waters.</p> <p>There's an even quirkier way to interact with fish here: hand-feeding the tarpon off the docks of Robbie's Marina (MM 77.5). Since 1976, countless Keys visitors have stopped to feed them, and more than 100 kinds of fish gather at the docks for their daily snacks. Feeding the fishies there is so popular, it's been named the No. 1 activity in all the Florida Keys.</p> <p>Islamorada is also a terrific spot to kitesurf, stand-up paddleboard, <a href="https://www.rd.com/list/best-hiking-trails/" rel="noopener noreferrer">go for a hike</a> or take a bicycle ride. Stop by the Laura Quinn Wild Bird Sanctuary, where injured or displaced birdies now make their homes. Or visit the History of Diving Museum, which boasts one of the world's largest collections of diving helmets.</p> <p><strong>Best beach:</strong> Anne's Beach is popular with families (and dogs) because of its shallow waters and lack of waves. Take a walk along the boardwalk or enjoy a picnic at one of the covered tables.</p> <p><strong>Where to eat:</strong> For a quintessential casual Florida Keys meal, go to the Hungry Tarpon. If you want more elegant fare, make reservations at Chef Michael's for creatively inspired local dishes.</p> <p><strong>Where to stay:</strong> When it's time to lay your head for the night, check in to one of the new oceanfront suites at <a href="https://www.tripadvisor.com/Hotel_Review-g34346-d84610-Reviews-Cheeca_Lodge_Spa-Islamorada_Florida_Keys_Florida.html" rel="noopener noreferrer">Cheeca Lodge & Spa</a>, or your own cottage at <a href="https://www.tripadvisor.com/Hotel_Review-g34346-d113464-Reviews-The_Moorings_Village-Islamorada_Florida_Keys_Florida.html" rel="noopener">The Moorings Village & Spa</a>.</p> <p class="listicle-page__cta-button-shop"><a class="shop-btn" href="https://www.tripadvisor.com/Hotel_Review-g34346-d84610-Reviews-Cheeca_Lodge_Spa-Islamorada_Florida_Keys_Florida.html">Book Now</a></p>

Mile marker: 90–63

Next up en route from Key Largo to Key West is the fisherman's paradise known as Islamorada. Considered the Sport Fishing Capital of the World, it's where backcountry sport fishing and saltwater fly-fishing got their start. Countless seasoned boat captains are ready for hire to take you out to catch the wahoo, marlin, mahi-mahi and tuna that swim in these waters.

There's an even quirkier way to interact with fish here: hand-feeding the tarpon off the docks of Robbie's Marina (MM 77.5). Since 1976, countless Keys visitors have stopped to feed them, and more than 100 kinds of fish gather at the docks for their daily snacks. Feeding the fishies there is so popular, it's been named the No. 1 activity in all the Florida Keys.

Islamorada is also a terrific spot to kitesurf, stand-up paddleboard, go for a hike or take a bicycle ride. Stop by the Laura Quinn Wild Bird Sanctuary, where injured or displaced birdies now make their homes. Or visit the History of Diving Museum, which boasts one of the world's largest collections of diving helmets.

Best beach: Anne's Beach is popular with families (and dogs) because of its shallow waters and lack of waves. Take a walk along the boardwalk or enjoy a picnic at one of the covered tables.

Where to eat: For a quintessential casual Florida Keys meal, go to the Hungry Tarpon. If you want more elegant fare, make reservations at Chef Michael's for creatively inspired local dishes.

Where to stay: When it's time to lay your head for the night, check in to one of the new oceanfront suites at Cheeca Lodge & Spa , or your own cottage at The Moorings Village & Spa .

<p><strong>Mile marker:</strong> 63–40</p> <p>Marathon is the island chain's top boating destination—and for good reason. The area boasts nearly 2,400 boat slips and plenty of facilities to accommodate sailors passing through. But you don't need your own boat to enjoy Marathon and its waters.</p> <p>For a truly different experience, hop on over to Cruisin' Tikis and have a floating tiki bar adventure. Sunset, mangrove and harbor cruises are all available, as is a swim-stop cruise for a chance to jump into the water.</p> <p>While you're here, you should also visit Pigeon Key, an island that is accessible by boat, trolley or walking the 2.2-mile Old Seven Mile Bridge. It has a museum to explore, either on a guided tour or on your own. The Bridge is open for walking, running, bicycling, rollerblading and, of course, watching the killer sunrises and sunsets.</p> <p><strong>Best beach: </strong>Sombrero Beach is one of the prettiest beaches in the Florida Keys—not to mention one of the <a href="https://www.rd.com/list/best-florida-beaches/">best beaches in Florida</a>. And it's not just popular with humans; sea turtles nest here between April and October.</p> <p><strong>Where to eat: </strong>For any meal, stop by Castaway, which has been serving guests for more than 70 years. Or make a night of it at Hide Away Café, which has an extensive wine list.</p> <p><strong>Where to stay:</strong> The <a href="https://www.tripadvisor.com/Hotel_Review-g34347-d6784786-Reviews-Faro_Blanco_Resort_Yacht_Club-Marathon_Florida_Keys_Florida.html" rel="noopener noreferrer">Faro Blanco Resort & Yacht Club</a> is set on the waterfront and gives you a taste of marina life. <a href="https://www.tripadvisor.com/Hotel_Review-g11962583-d113469-Reviews-Lime_Tree_Bay_Resort-Layton_Long_Key_Florida_Keys_Florida.html" rel="noopener">Lime Tree Bay Resort</a> on Long Key has spacious townhomes for rent.</p> <p class="listicle-page__cta-button-shop"><a class="shop-btn" href="https://www.tripadvisor.com/Hotel_Review-g34347-d6784786-Reviews-Faro_Blanco_Resort_Yacht_Club-Marathon_Florida_Keys_Florida.html">Book Now</a></p>

Mile marker: 63–40

Marathon is the island chain's top boating destination—and for good reason. The area boasts nearly 2,400 boat slips and plenty of facilities to accommodate sailors passing through. But you don't need your own boat to enjoy Marathon and its waters.

For a truly different experience, hop on over to Cruisin' Tikis and have a floating tiki bar adventure. Sunset, mangrove and harbor cruises are all available, as is a swim-stop cruise for a chance to jump into the water.

While you're here, you should also visit Pigeon Key, an island that is accessible by boat, trolley or walking the 2.2-mile Old Seven Mile Bridge. It has a museum to explore, either on a guided tour or on your own. The Bridge is open for walking, running, bicycling, rollerblading and, of course, watching the killer sunrises and sunsets.

Best beach: Sombrero Beach is one of the prettiest beaches in the Florida Keys—not to mention one of the best beaches in Florida . And it's not just popular with humans; sea turtles nest here between April and October.

Where to eat: For any meal, stop by Castaway, which has been serving guests for more than 70 years. Or make a night of it at Hide Away Café, which has an extensive wine list.

Where to stay: The Faro Blanco Resort & Yacht Club is set on the waterfront and gives you a taste of marina life. Lime Tree Bay Resort on Long Key has spacious townhomes for rent.

<p><strong>Mile marker:</strong> 40–4</p> <p>After crossing the Old Seven Mile Bridge out of Marathon, you'll find yourself in the Lower Keys, where natural habitats and wildlife refuges thrive. It's no wonder this part of the Florida Keys is known as the Natural Keys. You might even want to consider taking an <a href="https://www.rd.com/article/ev-road-trip/">electric vehicle on this road trip</a> so you don't disturb the animals.</p> <p>Your best chance to spot a native Key deer, a subspecies of the Virginia white-tailed deer that somehow made its way south, may be in the National Key Deer Refuge, comprised of 9,200 acres stretching from Bahia Honda Key to Sugarloaf Key on the edge of the Gulf of Mexico. More than 20 endangered and threatened plant and animal species can be found within the refuge. Take a quiet walk at dusk or dawn for your best chance to glimpse a Key deer, or join a ranger-led tour to learn more about the area.</p> <p>Aside from all the eco-friendly fun, Stock Island is well worth a stop. Their maritime history goes back generations, and the marina is filled with shrimping and fishing boats. Artists have been flocking to Stock Island, too, and share their works in galleries dotted across the small island.</p> <p><strong>Best beach: </strong>The shallow, clear water and white sand at Calusa Beach make it a locals' favorite. The beach is a perfect spot for snorkeling too.</p> <p><strong>Where to eat: </strong>In addition to the freshest of seafood, Big Pine Rooster serves up ribs and a special-recipe meatloaf. Or sip like the locals at No Name Pub, located on Big Pine Key.</p> <p><strong>Where to stay:</strong> Consider the waterfront <a href="https://www.tripadvisor.com/Hotel_Review-g34659-d603177-Reviews-Sugarloaf_Lodge-Sugarloaf_Key_Florida_Keys_Florida.html" rel="noopener noreferrer">Sugarloaf Lodge</a>, stay in an Airstream at <a href="https://www.tripadvisor.com/Hotel_Review-g34085-d113460-Reviews-Big_Pine_Key_Resort-Big_Pine_Key_Florida_Keys_Florida.html" rel="noopener noreferrer">Big Pine Key Resort</a> or pop a tent on one of the reserved campsites at Bahia Honda State Park.</p> <p class="listicle-page__cta-button-shop"><a class="shop-btn" href="https://www.tripadvisor.com/Hotel_Review-g34659-d603177-Reviews-Sugarloaf_Lodge-Sugarloaf_Key_Florida_Keys_Florida.html">Book Now</a></p>

The Lower Keys

Mile marker: 40–4

After crossing the Old Seven Mile Bridge out of Marathon, you'll find yourself in the Lower Keys, where natural habitats and wildlife refuges thrive. It's no wonder this part of the Florida Keys is known as the Natural Keys. You might even want to consider taking an electric vehicle on this road trip so you don't disturb the animals.

Your best chance to spot a native Key deer, a subspecies of the Virginia white-tailed deer that somehow made its way south, may be in the National Key Deer Refuge, comprised of 9,200 acres stretching from Bahia Honda Key to Sugarloaf Key on the edge of the Gulf of Mexico. More than 20 endangered and threatened plant and animal species can be found within the refuge. Take a quiet walk at dusk or dawn for your best chance to glimpse a Key deer, or join a ranger-led tour to learn more about the area.

Aside from all the eco-friendly fun, Stock Island is well worth a stop. Their maritime history goes back generations, and the marina is filled with shrimping and fishing boats. Artists have been flocking to Stock Island, too, and share their works in galleries dotted across the small island.

Best beach: The shallow, clear water and white sand at Calusa Beach make it a locals' favorite. The beach is a perfect spot for snorkeling too.

Where to eat: In addition to the freshest of seafood, Big Pine Rooster serves up ribs and a special-recipe meatloaf. Or sip like the locals at No Name Pub, located on Big Pine Key.

Where to stay: Consider the waterfront Sugarloaf Lodge , stay in an Airstream at Big Pine Key Resort  or pop a tent on one of the reserved campsites at Bahia Honda State Park.

<p><strong>Mile marker:</strong> 4–0</p> <p>You've made it to the end! Closer to Cuba than Miami, Key West is known for its nightly sunset celebrations, party atmosphere and laissez-faire vibe, but it's really so much more.</p> <p>If you're a writer or bookworm, you'll certainly want to make plans to visit the Ernest Hemingway Home & Museum, where you should keep an eye out for the famous six-toed cats. Then wander through Key West's Bahama Village, a 12-block area of historic homes and restaurants.</p> <p>Consider a day trip to Dry Tortugas National Park, about 70 miles west of Key West in the Gulf of Mexico, where you'll find some <a href="https://www.rd.com/list/states-hidden-gems/">hidden gems</a>. The island, accessible by boat or seaplane, is popular for snorkeling and feeling like you're on your own private island, not to mention touring the Civil War–era fort.</p> <p><strong>Best beach: </strong>Fort Zachary Taylor Beach—or Fort Zach, as locals call it—predates the Civil War and boasts the island's very best sandy stretch.</p> <p><strong>Where to eat: </strong>No visit to Key West is complete without a meal at Blue Heaven, where you can dine with wandering roosters for breakfast, lunch and dinner. Or snag a spot on the tiny balcony at Santiago's Bodega for tapas and flowing wine.</p> <p><strong>Where to stay:</strong> The boutique <a href="https://www.tripadvisor.com/Hotel_Review-g34345-d227346-Reviews-The_Gardens_Hotel-Key_West_Florida_Keys_Florida.html" rel="noopener noreferrer">Gardens Hotel</a>, the adults-only Kimpton Hotels <a href="https://www.tripadvisor.com/Hotel_Review-g34345-d296023-Reviews-Kimpton_Ridley_House-Key_West_Florida_Keys_Florida.html" rel="noopener noreferrer">Ridley House</a> or the new <a href="https://www.tripadvisor.com/Hotel_Review-g34345-d21408966-Reviews-The_Capitana_Key_West-Key_West_Florida_Keys_Florida.html" rel="noopener noreferrer">Capitana Key West</a>, to name a few. Wherever you stay, you're sure to find your place in Key West, and it's likely you'll follow so many others' lead and start planning your return visit before you even leave.</p> <p class="listicle-page__cta-button-shop"><a class="shop-btn" href="https://www.tripadvisor.com/Hotel_Review-g34345-d227346-Reviews-The_Gardens_Hotel-Key_West_Florida_Keys_Florida.html">Book Now</a></p>

Mile marker: 4–0

You've made it to the end! Closer to Cuba than Miami, Key West is known for its nightly sunset celebrations, party atmosphere and laissez-faire vibe, but it's really so much more.

If you're a writer or bookworm, you'll certainly want to make plans to visit the Ernest Hemingway Home & Museum, where you should keep an eye out for the famous six-toed cats. Then wander through Key West's Bahama Village, a 12-block area of historic homes and restaurants.

Consider a day trip to Dry Tortugas National Park, about 70 miles west of Key West in the Gulf of Mexico, where you'll find some hidden gems . The island, accessible by boat or seaplane, is popular for snorkeling and feeling like you're on your own private island, not to mention touring the Civil War–era fort.

Best beach: Fort Zachary Taylor Beach—or Fort Zach, as locals call it—predates the Civil War and boasts the island's very best sandy stretch.

Where to eat: No visit to Key West is complete without a meal at Blue Heaven, where you can dine with wandering roosters for breakfast, lunch and dinner. Or snag a spot on the tiny balcony at Santiago's Bodega for tapas and flowing wine.

Where to stay: The boutique Gardens Hotel , the adults-only Kimpton Hotels Ridley House  or the new Capitana Key West , to name a few. Wherever you stay, you're sure to find your place in Key West, and it's likely you'll follow so many others' lead and start planning your return visit before you even leave.

<p>Road-tripping from Key Largo to Key West, it's easy to appreciate all the natural beauty. That said, the Keys aren't just a terrific destination for <a href="https://www.rd.com/article/what-is-ecotourism/">eco-travelers,</a> but artists and history buffs too.</p> <p>It's easy for artists to find inspiration throughout the Florida Keys. Fortunately for road-trippers, there are many spots to stop and admire their work. One of the largest artists' communities in the Florida Keys is Stock Island in the Lower Keys, just about three miles from the commercial area of Key West. What was once a shrimping boat marina is now a blend of fishermen and painters, sculptors and other artisans who have created an energetic and supportive community.</p> <p>For history buffs, in addition to Pigeon Key in Marathon and the Civil War–era Fort Jefferson in Dry Tortugas National Park, other must-stops in Key West include the Audubon House & Tropical Gardens, Harry S. Truman Little White House and the Southernmost Point in the continental United States.</p>

Art and history in the Florida Keys

Road-tripping from Key Largo to Key West, it's easy to appreciate all the natural beauty. That said, the Keys aren't just a terrific destination for eco-travelers, but artists and history buffs too.

It's easy for artists to find inspiration throughout the Florida Keys. Fortunately for road-trippers, there are many spots to stop and admire their work. One of the largest artists' communities in the Florida Keys is Stock Island in the Lower Keys, just about three miles from the commercial area of Key West. What was once a shrimping boat marina is now a blend of fishermen and painters, sculptors and other artisans who have created an energetic and supportive community.

For history buffs, in addition to Pigeon Key in Marathon and the Civil War–era Fort Jefferson in Dry Tortugas National Park, other must-stops in Key West include the Audubon House & Tropical Gardens, Harry S. Truman Little White House and the Southernmost Point in the continental United States.

<p>Now that you're inspired to hit the road, it's time to start planning. After <a href="https://www.rd.com/article/road-trip-cost/" rel="noopener noreferrer">budgeting for a road trip</a>, your next step is to decide whether you will travel south from Key Largo to Key West, or north from Key West to Key Largo. Or maybe you'll opt for a roundtrip.</p> <p>If you're starting off in Key Largo, it's important to note that the Florida Keys Overseas Highway begins at the Miami-Dade/Monroe County line. So if you're flying to Florida, Miami International Airport (MIA) is the way to go. If you begin in Key West, the airport (EYW) is on the island.</p> <p>If you're already driving one of the <a href="https://www.rd.com/list/best-road-trip-cars/" rel="noopener noreferrer">best road trip cars</a> to get to Florida, you're all set. But if you need a loaner, choose one of the <a href="https://www.rd.com/list/best-cars-to-rent-for-a-road-trip/" rel="noopener noreferrer">best cars to rent for a road trip</a>. Consider packing these <a href="https://www.rd.com/list/road-trip-essentials/" rel="noopener noreferrer">road trip essentials</a> and download some of the <a href="https://www.rd.com/article/best-podcasts-for-road-trips/" rel="noopener noreferrer">best podcasts for road trips</a> to make the miles fly by.</p>

Planning your Florida Keys road trip

Now that you're inspired to hit the road, it's time to start planning. After budgeting for a road trip , your next step is to decide whether you will travel south from Key Largo to Key West, or north from Key West to Key Largo. Or maybe you'll opt for a roundtrip.

If you're starting off in Key Largo, it's important to note that the Florida Keys Overseas Highway begins at the Miami-Dade/Monroe County line. So if you're flying to Florida, Miami International Airport (MIA) is the way to go. If you begin in Key West, the airport (EYW) is on the island.

If you're already driving one of the best road trip cars to get to Florida, you're all set. But if you need a loaner, choose one of the best cars to rent for a road trip . Consider packing these road trip essentials and download some of the best podcasts for road trips to make the miles fly by.

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Will the HGTV Dream Home winner move from New York to live on Anastasia Island , Florida?

Time will tell what Marie Fratta, a veteran elementary school teacher from Westchester County, New York, will do. Fratta, who was picked out of 130 million entries for the 2024 HGTV Dream Home sweepstakes, was notified by the home and garden television network of her epic prize, and HGTV announced the news May 22, 2024, months after the contest ended. Voting was from Dec. 22, 2023, to Feb. 15, 2024 on HGTV and Food Network sites.

Like others before her, Fratta has to choose whether to become a Sunshine State resident or to take the cash option. The Anastasia Island location is the latest Florida site for the HGTV Dream Home sweepstakes contests since it started in 1997. Over the years, there have been five HGTV Dream Homes in Florida, more than any other state. On the flip side, there have been only two people from Florida who won an HGTV Dream Home since the sweepstakes contest began. Still, that's seven HGTV Dream Home ties to the Sunshine State.

Here's more info about the houses here and the Florida winners.

2024 HGTV Dream Home on Anastasia Island, Florida

The 2024 HGTV Dream Home on Anastasia Island, Florida, was  designed by architect Michael Stauffer  and built by local builder Glenn Layton Homes. The home's interior design was by Brian Patrick Flynn. The  three-bedroom, four-bathroom home  is about 3,300 square feet with views of the Matanzas River and the St. Augustine Lighthouse. Value of the total  Anastasia Island HGTV Dream Home  package was estimated at just over $2.2 million. In total, as winner of the 2024 HGTV Dream Home, Maria Fratta of Westchester County, New York, will receive:

  • Keys to the fully furnished home, which, according to rules, includes home furnishings, fixtures, artwork and merchandise for an approximate retail value of $2,069,595
  • A new Mercedes-Benz E Class sedan worth about $70,000, according to the rules
  • $100,000 cash

If Fratta decides to take the cash option, she'll receive $650,000 in cash, per contest rules.

2016 HGTV Dream Home on Merritt Island, Florida

FLORIDA TODAY reported David Rennie of Shelton, Connecticut,  won the 2016 HGTV Dream Home on Merritt Island , Florida, along with $250,000, a 2016 Bryant Sperenza model boat and 2016 GMC Acadia Denali car. The 3,150-square-foot remodeled home had Indian River water views in its backyard. It was a three-bedroom, two-story home off South Tropical Trail. Features included water views, a grand staircase, luxury dog house, pool and private dock. It had outdoor lounging areas, Florida-inspired decor, bold colors, three bathrooms and two half-bathrooms. Rennie, HGTV said, was chosen from 127 million entries.

HGTV valued the 2016 HGTV Dream Home prize package at $1.7 million. Rennie  chose the cash option , and the house was eventually listed at $1,530,000 a month after Rennie won, according to a  2016 story in FLORIDA TODAY . Real estate sites show the 2016 HGTV Dream Home on Merritt Island, Florida eventually sold for $1.3 million , FLORIDA TODAY reported.

Florida woman won 2009 HGTV Dream Home in California

Cheryl Smith of Lakeland, Florida, won the 2009 HGTV Dream Home in Sonoma, California.

Smith did not keep the three-bedroom, 3 1/2-bath home, and it was on the market for $2.2 million, according to a July 2009 SFGate.com story : "The Florida couple who won this year's dream-home lottery sold the property to developer Steve Ledson, who is now reselling it. Ledson designed and built the home for HGTV on his Armstrong Estates, a new development built to resemble a 'heritage neighborhood.' Surrounded by century-old oak trees, the home resembles a Victorian farmhouse, with generous spaces and front and back porches. A large family room opens to a patio and outdoor kitchen. HGTV had valued the home plus its decorator-selected furniture and a new car at $2 million."

2008 HGTV Dream Home in Islamorada, Florida

Stephanie Dee of Solon, Iowa, won the 2008 HGTV Dream Home in Islamorada, Florida.

HGTV notified Dee of her three-story "island oasis" grand prize in March 2008, and a family vacation to visit followed in June of that year. According to a January 2009 story on twincities.com , Stephanie Dee described the Islamorada home as "beautiful" and "amazing," with an ocean view from every floor.

By August 2009, the HGTV Dream Home was put on the market and eventually sold.

Florida postmaster won 2007 HGTV Dream Home in Colorado, years after winning a Florida lottery prize

Robert O'Neill of Brandon, Florida , won the 2007 HGTV Dream Home in Winter Park, Colorado.

According to a  March 2007 story on timesnews.net , O'Neill also won $13,000 from the  Florida Lottery  shortly after he retired in 1999. Eight years later, the story says, O'Neill won the Colorado HGTV Dream Home, which included the fully furnished 4,400-square-foot lodge-style home, a 2007 GMC Acadia, a matching "HGTV Doggy Dream Home" and $250,000 in cash for a total prize value of $2.5 million. Features of the four-bedroom, five-bathroom home included a wet bar, a kids "bunk room," a loft, stunning views of the Rocky Mountains, rustic exposed beams, stone fireplaces, a hot tub and patio.

Though O'Neill beat the odds of 41 million-to-1, the retired postmaster put the 2007 HGTV Dream Home up for sale shortly after winning the contest. Interested buyers popped up from across the country, Dennis Saffell, owner and broker of Coldwell Banker Mountain Properties, said in a  November 2007 Sky-Hi Daily News story . A pair of surgeons and their families from Denver eventually bought the dream home for about $2 million, the  Sky-Hi Daily News story  states: "We had a lot of people looking at it ... for its fame of being an HGTV home. And it ended up selling to someone who had no idea it was an HGTV home. They bought it because they liked it," Saffell had told  skyhinews.com .

2003 HGTV Dream Home in Mexico Beach , Florida

John Groszkiewicz of Erie County, Pennsylvania, won the 2003 HGTV Dream Home in Mexico Beach , Florida.

Features of the home include a great room, primary suite, bunk house, garden room and green house, as well as a private deck and zen-like spa deck. It also had access to the water and a boat house equipped with a fishing boat.

According to a  2006 article from the Pittsburg Post-Gazette , Groszkiewicz and his family visited the HGTV Dream Home several times before selling it shortly after Labor Day 2003 for about $800,000.

1999 HGTV Dream Home in Rosemary Beach, Florida

Belinda Brown of Kingston, Tennessee,  won the 1999 HGTV Dream Home in Rosemary Beach , Florida.

According to HGTV , the house nicknamed "tropical retreat" had a tin roof that reflected heat, making it cooler inside the home. The home and garden network highlighted the Dream Home's "wonderfully-livable outdoor room, called a loggia, from the Italian word for 'living place.' The loggia is furnished just like an indoor living space, with comfortable, inviting furniture and separate living and dining areas," the HGTV blog post read.

A February 2018 countryliving.com story states Belinda Brown tried to rent out her Rosemary Beach, Florida, Dream Home, but she sold it after two years.

Contributing: Samantha Neely, USA TODAY Network-Florida

Sangalang is a lead digital producer for USA TODAY Network-Florida. Follow her on  Twitter  or Instagram at  @byjensangalang . Support local journalism.  Consider subscribing to a Florida newspaper .

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