
Vacation rentals in Florida Keys
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Florida Keys
Guests agree: these stays are highly rated for location, cleanliness, and more.

ATLANTIS...Ocean Front Cottage Retreat!
ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need for the perfect getaway. Boat dock (25ft), HD TVs, washer & dryer, S/S appliances & gas cooking! Complimentary kayaks & bikes plus access to all the Venture Out Residential Condominium Community amenities: heated pool, Jacuzzi, kiddie pool, tennis, basketball & bocce courts, ocean bay swimming area, marina w/fuel, boat ramps & wash station, and a convenience market on-site!

Captain’s Quarters Ahoy Mateys! Florida, Keys
This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.

Turtle-By-The-Sea: the Best Deal in KCB!
A perfect get-away for couples or budget travelers, Turtle-by-the-Sea is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home. Shoot us a message & start planning your dream Keyscation!

Oceanfront Lookout Point w/two Kayaks & Deck
Lookout Point is Wide open breathtaking Water View , Amazing Sunrises with a cup of Morning coffee, Refreshing breeze, Sound of water and Rustle of palm trees will start your day… Fishing right from the property, Kayaking. Taking sunbath on Chaise lounges or Reading books or just sitting under Tiki having a nice conversations and enjoying beautiful scenery of the view. You will see fishes jumping out of water, seagulls trying to catch up it , you might see manatee swimming by or dolphins.

Charming Key Largo Cottage on the Water w/Kayaks!
Charming "Tiny House" Cottage on a main canal just two units from open water. Amazing location for boaters, fisherman and alike. This is a quaint and close knit RV park where you can keep to yourself or wander around and enjoy happy hour with new local friends. Bar none the best kayak, paddle board and fishing area. Two Tandem (each kayak accommodates two people) Kayaks and two paddle boards included in rental. Great outdoor space to dock your boat, fish off of or enjoy a few cocktails!

Flakey's
Flakeys, short for Florida Keys is everything you would expect to find on the small Caribbean island. Its paradise! Located in the heart of Islamorada there is no need for a car. You can walk or bike to the best restaurants, bars, beaches and shops this island has to offer. On Morada Way in the middle of the Art and Culture district. Everything at Flakeys is brand NEW! All new appliances, furniture and decor. Shabby Island Chic! Affordable, super clean and you can't beat the location.

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.

My Little Oasis3 Waterfront Retreat Key Largo
Best of the Best, very exclusive, located on the oceanfront with a million dollar view, this tiny house is on a higher level than the others, is comfortable and cozy. It is ideal for a couple who want to escape. The property is located on a residential island, restaurants, bars, stores and grocery stores are within a 15 minute drive from the property. Note: The upstairs room is not comfortable for seniors or adults, the ceiling height is 4 feet (an adult has to walk on his knees

Hidden Beach unit 1 The Perfect Place to stay
This place is extraordinary. There is nothing like it in Key West. Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlantic Ocean nestled between Key West’s best restaurant (Louie’s Backyard) and the beautiful, luxurious Reach Resort.Here, you can enjoy spectacular views and sunsets from one of the islands only private beaches or you can stroll through Old Town, an amazing architectural and botanical treasure.

New Aqua Lodge 2Beds 1 Bath with Full Kitchens
This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

Cudjoe Key Home with a View
We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina. On the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.

Private Pool Tropical Oasis - Centrally Located
Centrally located in the Florida keys, this beautiful three-bedroom home is steps away from fishing, restaurants, boat rentals and water sports. The property features a private and lush backyard filled with your own private pool, loungers and outdoor games. In the evening, unwind with a refreshing drink under the outdoor lighting or in the heated pool. The villa includes a high chair, pack and play, bed rails, booster seat, baby gate and kids dishware.
Popular amenities for Florida Keys vacation rentals
Florida Keys beach vacation rentals

Stunning Waterfront Condo with Double Balconies

2 bedroom & 25' Boat Dock Waterfront Atlantic Side

Romantic Bayside Guesthouse peaceful beach sunsets

Houseboat Getaway In Marathon

Beachfront Villa - Florida Keys

Hunter 26 Sailboat

NEW! CASA AZUL - Golf Cart, 2 Kings, Pool, Kayaks

Modern Beach Lake-Front House in Miami !
Private vacation rentals in Florida Keys

*August/September specials* off Grid Boat Key West

Waterfront Cozy Cottage with Boat Ramp & Dock!

Beach House in Marathon with Amazing Backyard!

Florida Keys Resort-Style Home w/ Pool & Dock 5/3

b watervibe

Beach House, Private Pool, Dock, Gulf View Sunsets

NEW! Private Pool, 50’ Dock, Kayaks, Waterfront

Las Olas
Florida Keys house rentals

Best Location in Marathon & KCB!

Tiny Home on Waterfront | Bay Views | Deck | Pool

Everglades-Homestead. Tropical Retreat. Miami-Keys

3/2 Home w Dock, lagoon, kayaks!

4BR 3B, Heated Pool & Spa, 60' Dock

Tropical Keys Retreat | Pool | Hot Tub | Cinema

Starlight Serenity - Hideaway with Stunning Views

Golf Coast Oasis near Sombrero Beach
Frequently Asked Questions
Where is Florida Keys located?
Florida Keys is a chain of islands stretching off the southern tip of Florida, surrounded by the Atlantic Ocean and Gulf of Mexico. The area is known for tropical scenery, marine life, and distinct communities rooted in maritime traditions.
When is the best time to visit Florida Keys?
Visitors often favor late winter and spring for milder temperatures around 66–81°F (19–27°C) and lighter rainfall. Summer months can be warmer, reaching near 91°F (33°C), with more frequent showers, but activities continue year-round.
What are some things to do near Florida Keys?
You can explore local coral reefs by snorkeling or diving, visit historic sites in Key West, and enjoy kayaking or fishing around the islands. The region also has public beaches, galleries, and culinary experiences shaped by coastal influences.
How is the weather near Florida Keys?
Florida Keys has a subtropical climate, with winter temperatures near 61–76°F (16–25°C) and warmer summers reaching 78–91°F (25–33°C). Rain is more frequent from May to October, so light clothing and sun protection are recommended throughout the year.
All about Florida Keys
From vibrant Key West to the mysteriously named No Name Key, the Florida Keys offer historical intrigue and geographical wonder in a graceful archipelago, stretching out from the Everglades towards Havana. Postcard-worthy turquoise waters make the Keys a popular destination for sports fishing, scuba diving, and boating. If you fancy a more leisurely set of activities during your visit, boat rides in the tropical sun and snorkeling let you set your own pace for exploring the dazzling coral islands.
The strong culinary culture of the Keys is centered around fresh seafood, from mahi-mahi to snapper to blackfin tuna, alongside other edible delights, like Key lime pie on a stick. For those wanting to explore both land and sea, consider venturing into the Mel Fisher Maritime Heritage Museum or the Key West Shipwreck Treasure Museum, both of which are excellent forays into the impact the ocean has had on the history of these islands.
What are the top things to do in Florida Keys?
Duval Street
Duval Street, running from Mallory Square to the Southernmost Point marker, is one of Key West’s most lively streets. Host to museums, shops, galleries, and cafes, Duval Street is great not only for people-watching, with its many annual parades and events, but also for learning about the history of the Florida Keys, with attractions such as the Ernest Hemingway Home and Museum, and the former Strand Theater.
Dry Tortugas National Park
Dry Tortugas National Park, 70 miles from Key West, is only accessible by boat or plane, but is a worthwhile stop on any trip to the Florida Keys. An archipelago of seven beach-ringed islands, one is taken up entirely by the preserved ruins of Fort Jefferson, which stands guard over the coral, seagrass, and shipwrecks that welcome snorkelers from around the world. Popular snorkeling spots are the Historic Coaling Pier, Fort Jefferson's moat wall, and Garden Key. Boaters can explore around Loggerhead Key's Little Africa Reef and the Windjammer Wreck.
Marathon
Not to be confused with the activity, or the location of the same name in Greece, Marathon is the sportfishing center of the Florida Keys. Charters are easily arranged here for deep-sea, reef, and flats fishing. A variety of beaches and beachfront restaurants line the strip, while the former Seven Mile Bridge on the island makes a scenic path for walkers, joggers, and cyclists.
Destinations to explore
- Miami Vacation rentals
- Four Corners Vacation rentals
- Miami Beach Vacation rentals
- Orlando Vacation rentals
- Fort Lauderdale Vacation rentals
- Tampa Vacation rentals
- Hollywood Vacation rentals
- Kissimmee Vacation rentals
- Key West Vacation rentals
- Cape Coral Vacation rentals
- Clearwater Vacation rentals
- St. Petersburg Vacation rentals
- Guesthouse rentals Florida Keys
- Mansion rentals Florida Keys
- Townhouse rentals Florida Keys
- Ski-in/ski-out rentals Florida Keys
- Rentals with an accessible height bed Florida Keys
- Private suite rentals Florida Keys
- Vacation home rentals Florida Keys
- RV rentals Florida Keys
- Rentals with a sauna Florida Keys
- Rentals with a home theater Florida Keys
- Boat rentals Florida Keys
- Pet-friendly rentals Florida Keys
- Rentals with a hot tub Florida Keys
- Rentals with lake access Florida Keys
- Houseboat rentals Florida Keys
- Fitness-friendly rentals Florida Keys
- Rentals with breakfast Florida Keys
- Serviced apartment rentals Florida Keys
- Bed and breakfasts Florida Keys
- Rentals with an accessible height toilet Florida Keys
- Beach house rentals Florida Keys
- Rentals with a patio Florida Keys
- Villa rentals Florida Keys
- Apartment rentals Florida Keys
- Luxury rentals Florida Keys
- Rentals with a washer and dryer Florida Keys
- Beach condo rentals Florida Keys
- Rentals with a kayak Florida Keys
- Campsite rentals Florida Keys
- Hotel rooms Florida Keys
- Waterfront rentals Florida Keys
- Cottage rentals Florida Keys
- Tiny house rentals Florida Keys
- Rentals with a fireplace Florida Keys
- Smoking-friendly rentals Florida Keys
- Bungalow rentals Florida Keys
- Rentals with pools Florida Keys
- Resort rentals Florida Keys
- Rentals with outdoor seating Florida Keys
- Rentals with an EV charger Florida Keys
- Boutique hotels Florida Keys
- Rentals with beach access Florida Keys
- Rentals with a fire pit Florida Keys
- House rentals Florida Keys
- Beachfront rentals Florida Keys
- Family-friendly rentals Florida Keys
- Condo rentals Florida Keys
- Bayfront Park
- Everglades National Park
- Brickell City Centre
- University of Miami
- Dolphin Mall
- Sombrero Beach
- Kaseya Center
- Bayside Marketplace
- LoanDepot Park
- John Pennekamp Coral Reef State Park
- Zoo Miami
- CG Cosmetic Surgery
- Key Biscayne Beach
- Dadeland Mall
- Biscayne National Park
- Crandon Beach
- Biltmore Golf Course Miami
- Schnebly Redland's Winery & Brewery
- Mia Aesthetics Miami
- Calusa Campground
- Coral Castle
- Avana Plastic Surgery
- Miami International Mall
- Homestead-Miami Speedway
- Things to do Florida Keys
- Art and culture Florida Keys
- Tours Florida Keys
- Nature and outdoors Florida Keys
- Food and drink Florida Keys
- Sports activities Florida Keys
- Sightseeing Florida Keys
- Things to do Florida
- Wellness Florida
- Art and culture Florida
- Tours Florida
- Entertainment Florida
- Sightseeing Florida
- Food and drink Florida
- Sports activities Florida
- Nature and outdoors Florida
- Things to do United States
- Tours United States
- Sightseeing United States
- Entertainment United States
- Sports activities United States
- Art and culture United States
- Wellness United States
- Nature and outdoors United States
- Food and drink United States





