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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.

Superhost
Apartment in Key West
Bella Vita: 1B/1B Condo for 2 Just Steps off Duval
1B/1B condo located in Old Town less than 1/2 block from Duval St. & a couple blocks from the Southernmost Point, Hemingway House & many other Key West attractions. Bella Vita accommodates 2 adults only and features a large porch with chairs & table, living room with leather sofa, galley kitchen with bar seating, king-size bed with Tempurpedic mattress, desk area, bathroom with large walk-in shower, wi-fi, sound machine, 2 Smart TVs, DVD players & BlueTooth stereo system with CD player & radio.
$275 per night
Superhost
Home in Key West
Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
Romantic Retreat is a free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.
$328 per night
Superhost
Condo in Key Colony Beach
Oceanfront Breeze Condo Stunning Views, Beach/Pool
Newly renovated ocean front condo with gorgeous, unobstructed views from every window. Unit #30 is a studio condo on the 1st floor only steps away from the private beach and heated pool. #30 features a fresh, clean interior with brand furnishings, bathroom and kitchen stocked with everything (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Guests enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.
$269 per night

Florida Keys beach vacation rentals

Superhost
Apartment in Key West
Key West - Sunrise ❀ The Green House
$279 per night
Superhost
Apartment in Key West
Duval St Apartment w/ Balcony w/parking Adult Only
$375 per night
Superhost
Guesthouse in Key West
Old Town - Room Opens to Pool and Garden
$268 per night
Superhost
Apartment in Key West
Duval Balcony - Street Suite
$265 per night
Superhost
Vacation home in Key West
Historic Cigar House. 3rd floor Suite W/Kitchen
$298 per night
Superhost
Apartment in Key West
Poolside Truman Annex 2 Bed | Conch Life Condo
$361 per night
Superhost
Apartment in Key West
Studio Blu - Key West, FL - Hip Studio in Old Town
$176 per night
Superhost
Tiny home in Key West
Modern studio half block from Duval with parking
$215 per night
Superhost
Condo in Key West
La Dolce Vita, Old Town Steps to Duval! 3 blks bch
$305 per night
Superhost
Tiny home in Key Largo
The Oasis in key largo with your own private beach
$195 per night
Superhost
Condo in Tavernier
SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!
$213 per night
Superhost
Apartment in Key Largo
Waterfront Studio 1| Kayaks | Pool |Bay View |Wifi
$169 per night

Private vacation rentals in Florida Keys

Superhost
Guest suite in Tavernier
POOL ! Key Largo! Tavernier! Welcome to Paradise!
$205 per night
Superhost
Cottage in Cudjoe Key
ATLANTIS...Ocean Front Cottage Retreat!
$549 per night
Superhost
Guesthouse in Key Largo
Bayside Cabin beach romantic sunsets & fishing.
$186 per night
Superhost
Condo in Key West
Large 2/2 Waterfront Condo Great View Pool & Dock
$156 per night
Superhost
Cottage in Islamorada
FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO
$146 per night
Superhost
Condo in Key West
A Perfect Getaway
$334 per night
Superhost
Apartment in Key West
KW Luxury 2/2 Beachfront resort Tropical Oasis
$411 per night
Superhost
Condo in Key West
Ocean Front Studio private Sandy Beach in Key West
$144 per night
Superhost
Condo in Key West
Hidden Beach unit 2, The Perfect Place To Stay
$592 per night
Superhost
Condo in Key Colony Beach
Beachside Unit 28 - Private Beach, Pool & Paradise
$240 per night
Superhost
Tiny home in Key Largo
Oceanfront Lookout Point w/two Kayaks & Dock
$229 per night
Superhost
Bungalow in Key West
Atlantis House's Palm Suite-voted top 25 in USA
$394 per night

Florida Keys fishing vacation rentals

Superhost
Condo in Key Largo
Oceanfront Condo w/Lake, Kayak, Paddleboard & Bike
$311 per night
Superhost
Apartment in Key Largo
Seaside Vista - Ocean Front 2/1 with dockage
$178 per night
Superhost
Home in Key Largo
Outdoor Paradise - Beach, Boats, Snorkeling & Sun!
$152 per night
Superhost
Apartment in Miami
Beautiful One Bedroom Condo 16ft Ceilings At The W
$279 per night
Superhost
Apartment in Sunny Isles Beach
SUNNY ISLES OCEAN VIEW HOTEL ROOM!!! (+hotel fees)
$109 per night
Superhost
Guest suite in Homestead
Entire Studio Near The Everglades & Key West.
$56 per night
Superhost
Condo in Key Largo
Kawama Suntastic @ Key Largo
$192 per night
Superhost
Apartment in Key Largo
“Kawama Sunset”2 BD/3-D Corner/ Lagoon-Free Cancel
$221 per night
Superhost
Boat in Key West
ALL INCLUSIVE! Snorkel/Sail/Spear Fish/Fishing/Fun
$728 per night
Superhost
Condo in Palm Beach
Tropical Beach Condo - Pool, Parking, 86" TV, WiFi
$154 per night
Superhost
Cottage in Miami Lakes
* Lake Cottage * SpaLike Bath *
$102 per night
Superhost
Guesthouse in Palm Beach
Palm Beach Island Private Carriage House!
$243 per night

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.

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