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Florida Keys
Key Largo - ALL

Key Largo
Islamorada - ALL

Islamorada, Plantation Key, Tavernier, Windley Key
Marathon - ALL

Boot Key, Coco Plum Beach, Conch Key, Duck Key, Grassy Key, Key Colony Beach, Long Key, Marathon, Seabird Key, Sombrero Beach
Lower Keys - ALL

Big Pine Key,
Big Torch Key, Cudjoe Key, Little Torch Key, Melody Key, Ramrod Key, Sugarloaf Key, Summerland Key
Key West - ALL

Key West, Old Town

Florida Keys Vacation Rentals - All Listings

Welcome to the Florida Keys, where your next vacation rental is awaiting you. Click on one of the cities above or on the map to see a list of Florida Keys vacation rentals available.

Select Florida Keys Vacation Rental Properties:
Key West Charm
Key West
Weekly rates from
$3,500

4 Bedrooms

Big Pine Key
Monthly Rates From
$4,500

6BR 3BA
Ocean side Water front Vacation Rental in the Florida Keys
Marathon
Weekly rates from
$1,600

4 BR 4 BA
Sleeps 4-10

Grassy Key
Marathon

Weekly Rates From
$5,500

6BR 5.5BA

Summerland Key
Lower Keys

Monthly Rates From
$6,900

4BR 4BA

Key West
Monthly Rates From
$5,500

5BR 5.5BA
Key Largo Yacht Rental
Key Largo
Yacht Rental
Weekly Rates From
$840
Luxury Beach Home Vacation Rental in Marathon Florida
Marathon
Email for Weekly
Rates

4 BR 4.5 BA
Vacation Rental Condo with Private Beach and Pool in Key Colony Beach, Florida
Key Colony Beach
Weekly rates from
$1,000

2 BR 2 BA
Oceanfront Condo Rental in Key Largo Florida
Key Largo
Nightly rates from
$199

2 BR 2 BA
Vacation Condo Rental in Key Largo Florida
Key Largo
Nightly rates from
$199

2 BR 2 BA
Ocean View Luxury Vacation Rental in Key West Florida
Key West
Weekly rates from
$2,000

3 BR 2 BA
Key West Vacation Rental Condo
Key West
Weekly rates from
$1,200

2 BR 2 BA

Bayside Keys FL
Weekly rates from
$$1,095

varies BR 2 BA

keys kottage
Weekly rates from
$1,200

2 BR 2 BA
 
Select Florida Keys Vacation Property Managers:

TrumanAnnex.com
Key West, Florida
Rates Vary
We are the exclusive on-site rental agency for the Truman Annex and Key West Golf Club.
Lara Group
Florida Keys Vacation Rentals
Florida Keys, Florida
Rates Vary
Florida Keys Vacation Rentals manages hundreds of vacation rental properties ranging from luxurious to budget-conscious throughout The Florida Keys including Key West, the Lower Keys, the Middle Keys, Islamorada & Key Largo.
Lara Group
Rent KW Vacations
Key West, Florida
Rates Vary
Rent a private home, cottage, villa, or condo as an alternative to your typical Key West hotel stay.

American-Paradise
Florida Keys, Florida
Rates from $1,100 / week
American Paradise Florida Keys Vacation Rentals.
Keys Holiday Rentals in the Florida Keys
Keys Holiday Rentals
Florida Keys, Florida
Rates Vary
Let me put my knowledge, experience, and dedication to work for you. Give me a call today and I will immediately get to work for you.
Vacation Rentals from Barefeet Rentals
Barefeet Rentals
Key Largo
Rates Vary
Barefeet Rentals is located in the Upper Florida Keys on the island of Key Largo and only a short drive to Islamorada, surrounded by the azure waters to the east of the Atlantic Ocean and the calm bay waters of the northern Gulf of Mexico known locally as Florida Bay.
Vacation Rentals in Key West Florida from Vacation-Homes-of-Key-West.com
Vacation Homes of Key West
Key West
Rates Vary
From charming little cottages to elegant luxurious estates, experience the original island charm of Key West through our variety of top quality vacation rental properties.

At Home In Key West Inc.
Key West, Florida
Rates Vary
Located throughout Key West many homes, cottages and compounds are open for vacation rentals.

Reny My Island
Key West, Florida
Rates Vary
Your Florida Keys Vacations Destination for Waterfront Homes & Condo's, Free Private Islands & Houseboat Rentals. Marathon Florida, known as the "Heart of the Keys" is suitably located in the middle of the Florida Keys.

Florida Keys The American Caribbean

Dividing the Atlantic Ocean in the east from the Gulf of Mexico in the west rests the Florida Keys; the only living, coral barrier reef in North America. The Florida Keys is an archipelago of about 1700 isles and full of distinctive plant and animal species. The 110 miles of the Florida Keys offers many activities to those who venture there. Sport fishing, diving, snorkeling, and boating are equally popular and visitors can hike trails, go bird watching, camp and take eco-tours amongst the islands. Life is easy going and there are world famous fishing opportunities everywhere. Explore a tropical destination in America without leaving the United States and book a Florida Keys vacation rental.

Key West - The Last Resort
Everything which was old is new again in Key West and Old Town. Also known as the last resort, Key West is the southernmost city in the continental U.S. and is well known for its bustling nightlife, culture, and the restoration of old homes and businesses. Tour the streets where mimes, musicians and artists entertain your imagination or sip coffee in a nearby sidewalk café. There are plenty of open-air bars and pubs where you can dance the night away. Key West is host to festivals, fishing tournaments, powerboat races, Pride Week, Fantasy Fest and other cultural activities. The 2 x 4 mile island is packed with resorts, hotels, B&B’s, campgrounds and of course, Key West vacation rentals. Everything is just a short distance away and if your own tw feet can’t carry you to your nearest destination, there are plenty of taxis, tour trains, trolleys, mopeds and pedicabs to get you where you want to go. There surely is something for everyone, especially for fisherman. Fly fish, or try wreck and reef fishing for tarpon, bonefish, shark, barracuda, grouper, cobia, kingfish or snapper. If fishing isn’t on the list, maybe scuba diving is. Take night dives on wrecks or snorkel amongst the tropical fish and lush marine plant life. Golf at the Key West Golf Club, get spooked on a ghost tour, visit the Ernest Hemingway Museum, or visit the Key West Aquarium to be dazzled by rare and exotic creatures.

Lower Keys – Relaxed and Low Key
For the most relaxed atmosphere and easy access to the water, stay in a Lower Keys vacation rental.
Here, every day is just as pleasant as the next and is arguably the most beautiful 30 mile stretch in the Florida Keys. Don’t expect to find too much of the modern world in the Lower Keys, as commercial development is limited. Dip your feet in rare white sandy beaches of Bahia Honda State Park as you make your way into the Lower Keys from Marathon. It is said that Bahia Honda State Park contains one of the most beautiful beaches in the world and is also home to rare plants and flowers. Pitch a tent at the campgrounds, launch a boat in the marina, or park the RV because you’ll want to stay here where the views are eye-catching and picturesque. Big Pine Key is home to the Looe Key Marine Sanctuary and the National Key Deer Refuge. Here, shops host day and nighttime diving and snorkeling adventures where up to a 150 varieties of fish can be seen. Pine Key is also the main shopping hub of the Lower Keys were tourists can shop for a variety of arts, crafts and other treasures. Arrange a small plane ride or skydive from Sugarloaf Key or accommodate yourself in lovely vacation rentals in Summerland Key, Big Torch and Little Torch Keys, Cudjoe Key, Big Coppitt Key, and Ramrod Key.

Marathon – The Heart of the Florida Keys
Making your way up the famous Seven Mile Bridge from the Lower Keys, you’ll come upon the heart of the Florida Keys: Marathon. Marathon is best known for its many vacation resorts, homes, and luxury accommodations and its here where tourists can find the well kept communities of Sombrero Beach and Key Colony Beach. Other great Marathon vacation rentals starting from the Seven Mile Bridge are located in Pigeon Key, Knight Key, Boot Key, Crawl Key, Grassy Key, Duck Key, Conch Key, and Long Key. There’s the Turtle Hospital in Marathon and The Dolphin Research Center in Grassy Key where tourists can learn and swim with bottle nose dolphins. With a Marathon vacation rental, visitors will enjoy some of the best water sports in the world including, snorkeling, diving, and fishing from the docks of Boot Key Harbor. There are great opportunities to shop for gifts and crafts or dine at some of the nicest restaurants the Florida Keys can offer. Guests can also kayak in the shallow waters, camp, or even venture off on eco-tours. Perhaps one of the best kept secrets is Crane Point Hammock where visitors can enjoy nature trails and get an eyeful of wild flowers and tropical trees. The 64 protected acres of Crane Point Hammock are also home to the Marathon Wild Bird Center, the Museum of Natural History, and the Children’s Museum where children can marvel at the 15,000-gallon Tropical Lagoon.

Islamorada – World Famous Sport Fishing
Just south of Key Largo rests Islamorada: the sport fishing capital of the world. Guests of Islamorada vacation rentals can catch sailfish in the winter months or enter in one of the numerous fishing tournaments held each year. Islamorada is a fisherman’s paradise, containing the oceans most sough after game fish: bonefish, tuna, tarpon and sailfish. For the freshest seafood, bring your catch to a local restaurant and have it cooked for you. Visitors can fish for fun along wrecks and reefs or scuba-dive amongst the tropical marine life at the Windley Key Quarry Fossil Reef. At Windley Key, visitors can walk amongst the trails and view dolphins and sea creatures at the Windley Key’s Theater of the Sea. Additional trails and camping opportunities are offered at the Long Key State Recreational Area. Tour with charter boat captains and back country guides at Islamorada and shop at the many arts and crafts stores offered in Plantation Key. There’s always a wide variety of water activities which include: kayaking, jet skiing, parasailing, boating, and romantic sunset cruises. Waterfront restaurants are the perfect setting for watching the sunset over the purple isles of Islamorada.

Key Largo – Diving Capital
Get the ultimate diving experience in the Florida Keys by visiting the John Pennekamp State park in Key Largo. Here, visitors can take guided trips to the park and to sunken wrecks to view fascinating coral formations. John Pennekamp State Park was the first underwater park in the United States and is also home to the Coral Reef Theater. Guests can snorkel, dive, canoe, kayak and even camp on its grounds. Getting to Key Largo is easy; it’s the first stop down the Overseas Highway after leaving the mainland of Florida. Kayakers, birders and eco-tourists will love Key Largo’s close proximity to the Everglades National Park in the east. The Florida Keys National Marine Sanctuary contains the wreck of Spiegel Grove, a navy ship sunk to create a new coral reef and there is also a large unsettled area of Key Largo, devoted to protecting the American Crocodile. Key Largo is mainly known for its diving adventures, but is also famous for sport fishing as well. Sailfish, bonefish, redfish, and tarpon can be caught along the Atlantic Shallows or in the Florida Bay. For those looking to experience this underwater world of Key Largo, there are numerous Key Largo vacation rentals, resorts, and hotel accommodations.
 
Featured Locations:
Old Town Key West City Key West Summerland Key Sugarloaf Key Ramrod Key Little Torch Key Cudjoe Key Lower Keys Long Key Grassy Key Duck Key Boot Key Key Colony Key Colony Beach Conch Key Sombrero Beach MarathonCity Marathon Tavernier Plantation Key Windley Key Islamorada2 Islamorada Key LargoCity Key Largo

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