Florida Keys vacation rentals

Book unique homes, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Florida Keys

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

Guest favorite
Guest suite in Marathon
Casa Mariposa: Easy walk to Sombrero Beach
Book your relaxing getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated a top 15 cozy retreat in the Keys, 1 0f 24 amazing AirBNB rentals in the Keys, and, in 2023, 1 of 23 Amazing Airbnbs In Florida Keys. Step out from your private suite to our 50' lap pool surrounded with tropical foliage, large patio, and tropical gardens. Avoid beach parking fees with a short walk from your suite at Casa Mariposa! Contact us if you are interested in other lengths of stay.
May 16 – 23
G$39,527 GYD per night
4.98 out of 5 average rating, 177 reviews
Guest favorite
Home in Marathon
Oceanfront Tiny Villa in the Heart of the FL Keys
Welcome to your happy place in paradise! Our oceanfront villa is located on Duck Key right outside of Marathon and next to the world famous Hawks Cay Resort. Halfway between Key Largo and Key West, it’s the perfect location to explore all our island paradise has to offer. Enjoy world class fishing, diving and snorkeling or kick back with a cold beverage and enjoy a stunning sunset on one of our covered porches. And always remember…it’s 5 o’clock somewhere!!
May 30 – Jun 6
G$88,170 GYD per night
4.96 out of 5 average rating, 114 reviews
Guest favorite
Guesthouse in Key Largo
Bayside Cabin beach romantic sunsets & fishing.
Cabin /Guesthouse beach fishing pier, sunsets watching romantic peaceful setting lush gardens with private parking access to all for you to enjoy and relax surrounded by nature wildlife at its best birds, iguanas, manatees, dolphin’s, eagles only a short walk to the beach and fishing pier, enjoy the immense boats cruising by, relax sipping your favorite cocktail. Bring your snorkeling gear and fishing tackle you will catch dinner 4 sure 😂
Aug 9 – 16
G$37,269 GYD per night
4.88 out of 5 average rating, 362 reviews

Popular amenities for Florida Keys vacation rentals

Florida Keys beach vacation rentals

Guest favorite
Condo in Key Colony Beach
Keys Breeze Ocean View Condo & Pool - Key Colony
Oct 9 – 16
G$51,239 GYD per night
4.98 out of 5 average rating, 187 reviews
Guest favorite
Cottage in Islamorada
1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON
Jul 5 – 12
G$35,376 GYD per night
4.85 out of 5 average rating, 121 reviews
Guest favorite
Tiny home in Key Largo
The Oasis in key largo with your own private beach
Dec 17 – 24
G$50,716 GYD per night
4.97 out of 5 average rating, 158 reviews
Guest favorite
Apartment in Key West
At Mine | Lovely Suite steps from Duval Street
May 11 – 18
G$62,787 GYD per night
4.93 out of 5 average rating, 949 reviews
Guest favorite
Cottage in Key Largo
Charming Key Largo Cottage on the Water w/Kayaks!
G$65,281 GYD per night
4.96 out of 5 average rating, 139 reviews
Guest favorite
Apartment in Key West
Bella Vita: 1B/1B Condo for 2 Just Steps off Duval
Dec 2 – 9
G$57,514 GYD per night
4.97 out of 5 average rating, 437 reviews
Guest favorite
Cottage in Little Torch Key
Waterfront Cozy Cottage with Boat Ramp & Dock!
Feb 8 – 15
G$98,564 GYD per night
4.91 out of 5 average rating, 142 reviews
Superhost
Houseboat in Key West
Happys Houseboat
Jun 2 – 9
G$80,426 GYD per night
4.85 out of 5 average rating, 162 reviews
Superhost
Condo in Tavernier
SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!
Sep 3 – 10
G$44,986 GYD per night
4.88 out of 5 average rating, 218 reviews
Superhost
Condo in Key Colony Beach
Beachside Unit 28 - Private Beach, Pool & Paradise
Nov 10 – 17
G$42,351 GYD per night
4.79 out of 5 average rating, 102 reviews
Guest favorite
Vacation home in Key Largo
Waterfront, GROUND LEVEL, Awesome Sunsets!!!
Jul 30 – Aug 6
G$44,846 GYD per night
4.99 out of 5 average rating, 134 reviews
Guest favorite
Home in Marathon
Sea Ray Cove , 75’ boat dock, 1 block from beach!
Dec 18 – 25
G$158,140 GYD per night
4.99 out of 5 average rating, 103 reviews

Private Florida Keys vacation rentals

Superhost
Villa in Marathon
New Aqua Lodge 2Beds 1 Bath with Full Kitchens
Dec 19 – 26
G$66,910 GYD per night
4.88 out of 5 average rating, 128 reviews
Guest favorite
Home in Key Largo
Your Keys Getaway!
Nov 5 – 12
G$34,542 GYD per night
4.9 out of 5 average rating, 343 reviews
Guest favorite
Home in Marathon
Marathon one-level home on the Marina - with slip!
Nov 25 – Dec 2
G$106,012 GYD per night
4.97 out of 5 average rating, 113 reviews
Guest favorite
Guesthouse in Key Largo
Oceanside, 1 bedroom, Bungalow in Key Largo
Dec 3 – 10
G$36,824 GYD per night
4.9 out of 5 average rating, 174 reviews
Guest favorite
Home in Islamorada
Flakey's
Oct 5 – 12
G$47,684 GYD per night
4.97 out of 5 average rating, 161 reviews
Guest favorite
Guest suite in Tavernier
POOL ! Key Largo! Tavernier! Welcome to Paradise!
Jun 24 – Jul 1
G$56,557 GYD per night
4.97 out of 5 average rating, 239 reviews
Superhost
Houseboat in Key West
The Crystalmarine Suite – Rustic Luxury on the Sea
Jan 31 – Feb 7
G$95,159 GYD per night
4.96 out of 5 average rating, 26 reviews
Guest favorite
Home in Marathon
Beach House, Private Pool & Dock, Gulf Sunset view
Nov 2 – 9
G$102,777 GYD per night
4.97 out of 5 average rating, 29 reviews
Superhost
Home in Upper Sugarloaf Key
Bungalows at Sugarloaf Beach - The Lighthouse
Jul 29 – Aug 5
G$150,006 GYD per night
4.84 out of 5 average rating, 38 reviews
Guest favorite
Guest suite in Key Colony Beach
Turtle-By-The-Sea: the Best Deal in KCB!
May 5 – 12
G$33,851 GYD per night
4.99 out of 5 average rating, 78 reviews
Guest favorite
Home in Key Largo
The Paradise 2
Sep 19 – 26
G$61,547 GYD per night
5.0 out of 5 average rating, 37 reviews
Guest favorite
Tiny home in Key Largo
Oceanfront Lookout Point w/two Kayaks & Dock
Dec 30 – Jan 6
G$50,313 GYD per night
4.98 out of 5 average rating, 53 reviews

Florida Keys home rentals

Guest favorite
Home in Cudjoe Key
Newly Renovated Oceanside House with Pool
Apr 16 – 23
G$73,677 GYD per night
4.89 out of 5 average rating, 178 reviews
Guest favorite
Home in Key Largo
Key Largo Waterfront Home with Tiki & Boat Dock
Apr 23 – 30
G$52,285 GYD per night
4.96 out of 5 average rating, 131 reviews
Superhost
Home in Key Colony Beach
Waterview from three sides, Cabana Club, 30' Docks
Dec 9 – 16
G$62,115 GYD per night
4.82 out of 5 average rating, 127 reviews
Guest favorite
Home in Key Largo
Little Cottage on an island
May 12 – 19
G$31,371 GYD per night
4.98 out of 5 average rating, 64 reviews
Guest favorite
Home in Marathon
P30 - 1200 30th
Aug 17 – 24
G$91,512 GYD per night
5.0 out of 5 average rating, 8 reviews
Guest favorite
Home in Marathon
Paradise in the Keys
May 31 – Jun 7
G$156,855 GYD per night
5.0 out of 5 average rating, 16 reviews
Guest favorite
Home in Marathon
Searenity Vacation Rental! Pool, Tiki Hut, Dockage
Sep 23 – 30
G$76,336 GYD per night
4.97 out of 5 average rating, 64 reviews
Superhost
Home in Marathon
Oceanfront mermaid house pool and dock
Feb 10 – 17
G$104,570 GYD per night
4.93 out of 5 average rating, 56 reviews
Guest favorite
Home in Marathon
100' Dockage, Pool, Kayaks, Paddle Board, Bikes!
Jan 11 – 18
G$121,600 GYD per night
5.0 out of 5 average rating, 29 reviews
Guest favorite
Home in Duck Key
Private Pool Tropical Oasis - Centrally Located
Nov 15 – 22
G$99,914 GYD per night
5.0 out of 5 average rating, 27 reviews
Guest favorite
Home in Key Colony Beach
IrishPirate! KCBw/Cabana C Pool, Beach, Bikes&MORE
Aug 16 – 23
G$67,971 GYD per night
5.0 out of 5 average rating, 28 reviews
Guest favorite
Home in Marathon
4BR Sombrero Beach House on Canal w Dock & Pool
Oct 26 – Nov 2
G$110,306 GYD per night
5.0 out of 5 average rating, 5 reviews

Your guide to Florida Keys

All About The 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.


The best time to stay in a vacation rental in Florida Keys

The best time to look for Florida Keys vacation rentals is between March and May. There are typically fewer crowds during this time and the weather is still warm without being humid, unlike in the muggier summer months.. The islands also host a variety of events in the spring. The 7 Mile Bridge Run in April is an annual marathon spanning the entirety of one of the island’s bridges. The Taste of Key West, also in April, is an annual celebration of the various cuisines that call the archipelago home, and feature everything from fine dining to seafood shacks and food trucks. The Key West Songwriters’ Festival in May has been going strong for 25 years and features dozens of performers across genres such as country, reggae, and rock.


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

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