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Key West vacation rentals

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Top-rated vacation rentals in Key West

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

Condo in Key West
WALK TO BEACH, MALLORY SQUARE, DUVAL STREET
Key West is like a little piece of the Caribbean, always warm with lovely turquoise waters. It's a short walk to Mallory Square, Hemingway's Home, the Truman White House, Duval Street, a Maritime Museum and the Eco Discovery Center. You're just a walk away from Zachary Taylor Park (where you can do yoga on the beach, swim, snorkel, or hang hammocks between the palms). We’re near numerous shops, restaurants, and museums. Enjoy coffee in the morning, wine at night on our oversized deck.
$330 per night
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Home in Key West
Relaxing Getaway - Duval Duplex - Free parking
Come stay in paradise! Golf cart available for rent! We are perfectly located one block from Duval Street but in a tranquil and relaxing location. We are only 3 blocks from the beach, 3 blocks from an off site pool, a short walk to southernmost point, and right in the heart of Key West. Close to everything. The location can’t get any better! free parking! Newly renovated & comes with a king size bed, outdoor furniture and beach chairs. This is everything you need! 28 day stays available!
$277 per night
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Guest suite in Key West
Tennessee Williams' Rose Tattoo Apartment Old Town
The Tennessee Williams' "Rose Tattoo" Studio is located in the locals area of Old Town, Key West. It is a quick 5 to 10 minute bike ride from Duval, or 15 minute walk. About 10 blocks on residential streets. This large studio is on the upper floor of a century old Key West converted commercial building. The Oscar winning film the "Rose Tattoo" was filmed partially here on location in the 1950s. This home is a monthly rental.
$110 per night
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Stay near Key West's top sights

Photo of Mallory Square
Mallory Square100 locals recommend
Photo of Southernmost Point of the Continental US
Southernmost Point of the Continental US64 locals recommend
Photo of The Ernest Hemingway Home and Museum
The Ernest Hemingway Home and Museum103 locals recommend
Photo of Fort Zachary Taylor Historic State Park
Fort Zachary Taylor Historic State Park47 locals recommend
Photo of Key West Butterfly and Nature Conservatory
Key West Butterfly and Nature Conservatory56 locals recommend
Photo of Higgs Beach
Higgs Beach21 locals recommend

Key West house rentals

Home in Key West
Lil' Bit- Updated Cottage In Quiet Neighborhood!
$265 per night
Home in Key West
Home Away from Home with Free parking
$328 per night
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Home in Key West
Gulf Getaway - Quiet Condo w/ Pool and Parking!
$432 per night
Home in Key West
Mango Cottage- 2 bedroom 2 bath with private pool
$631 per night
Home in Key West
Private 2BR with Pool in Old Town Key West
$420 per night
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Home in Key West
Downtown Waterfront 2/2 Dock & Pool Pet-Friendly
$359 per night
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Home in Key West
Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
$498 per night
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Home in Key West
Royal Poinciana Cottage-
$448 per night
Home in Key West
Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
$510 per night
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Home in Key West
Charming home in Old Town, walk to shops & restaurants - dog-friendly
$145 per night
Home in Key West
Robinson Crusoe Cottage- Shared Pool
$483 per night
Home in Key West
Lennon's Lodge, Luxury Accommodations for up to 6!
$661 per night
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Key West cottage rentals

Cottage in Key West
Cozy Cottage with Porch, WiFI, AC, & Amazing Walking Locale - Small Dogs OK
$350 per night
Cottage in Key West
Tranquil Dog-friendly Getaway with Shared Pool, WiFi, & AC - Snowbirds Welcome
$384 per night
Cottage in Key West
Namaste : A blissful one bedroom cottage designed with relaxation in mind.
$484 per night
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Cottage in Key West
The Dancing Rooster
$661 per night
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Cottage in Key West
Darling of Duval in Old Town - Estate Cottage + Spa + Last Key Services…
$526 per night
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Cottage in Key West
Paradise in the off-season. Book Now for summer!
$327 per night
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Cottage in Key West
1 bedroom Cottage
$342 per night
Cottage in Key West
Pete's East Cottage: Cypress east cottage steps from Duval
$361 per night
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Cottage in Key West
Colony Poolside: A charming bungalow near Duval Street
$341 per night
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Cottage in Key West
Oasis in old town Key West - private heated pool!
$180 per night
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Cottage in Key West
Bali Hideaway: A studio cottage that's perfect for two
$367 per night
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Cottage in Key West
The Sunshine House, Best Location in Key West!
$160 per night

Key West bungalow rentals

Bungalow in Key West
Island Style --
$545 per night
Bungalow in Key West
Fleming-O in Old Town close to Duval
$491 per night
Bungalow in Key West
Atlantis House's Banyan Suite-voted top 25 in USA
$355 per night
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Bungalow in Key West
Secret Courtyard- Lush tropical Hideaway just steps from Duval street
$656 per night
Bungalow in Cudjoe Key
Cudjoe Key OCEANFRONT 2B/2B in gated community!!
$221 per night
Bungalow in Key West
NEW LISTING! Newly renovated tropical oasis! POOL!
$436 per night
Private room in Key West
Heated Pool. Dog friendly. 30-day min. rental.
$150 per night
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Bungalow in Key West
Atlantis House's Palm Suite-voted top 25 in USA
$398 per night
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Bungalow in Cudjoe Key
Island Therapy
$215 per night
Bungalow in Key West
Beautiful three bedroom bungalow with Private pool
$425 per night
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Bungalow in Cudjoe Key
Treasure Isle at Parks End - Venture Out 062
$259 per night

Stays in Truman Annex

Rental unit in Key West
Poolside Truman Annex 2 Bed | Conch Life Condo
$597 per night
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Condo in Key West
Key West Paradise Poolside
$450 per night
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Rental unit in Key West
Key West - Sunset ❀ The Green House
$417 per night
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Condo in Key West
Spacious, waterfront condo w/ a full kitchen, shared pool, & furnished balcony
$552 per night

Your guide to Key West

All About Key West

Key West is a town that overflows with zest: turquoise waters and sandy beaches, dive bars that never seem to close, stunning sunsets, pastel-hued homes, great American literary legacies, and a sordid haunted past. Chow down on key lime pie and conch fritters, snap a pic at the southernmost point of the continental United States, and take in as much sea and sun as your eyes can handle.

Key West sits right across the Florida Strait from Cuba, and the influence can be felt in many of the island’s favorite haunts, where you can learn to dance the salsa, sample locally distilled rum, and pile your breakfast plate high with sweet fried plantains and savory beans. However you spend your days, make sure that you’re back in Mallory Square before sunset, when live music from restaurant patios and vendors’ stalls fills the pedestrian-only square and people celebrate the show-stopping sunset with all the fanfare it deserves.


When is the best time to stay in a vacation rental in Key West?

Winter is the most popular season in Key West, as the hot weather draws sun-seekers to the beaches, especially around the December holidays. You can also come in spring for sun and fewer crowds — despite Key West’s bustling nightlife scene, it isn’t typically hit by Spring Break crowds like other places in Florida. It’ll be warm enough to get in the water and enjoy beach time, with fewer people than in winter. Despite a September to November hurricane season, autumn is also a good time to check out Key West’s museums or to revel in the hedonistic Fantasy Fest while enjoying cooler air.


What are the top things to do in Key West?

Snorkeling

Home to the only living Barrier Reef in the continental United States, Key West has some of the most incredible snorkeling in the world. Head out to the cluster of tiny islands known as the Dry Tortugas National Park for the best of the best: this area is home to unspoilt coral reefs, hundreds of species of tropical fish, starfish, and conch.

Ghost tours

Key West is rumored to be one of the most haunted cities in America, in juxtaposition with its sunny, good-time appearance. For fans of classic horror, be sure to ask about a famous local doll and the film franchise he inspired. Listen to ghost stories on board a spooky train tour, go on a guided walk around town, or check out the quirky inscriptions on the local graves at the cemetery.

Key lime pie

Key lime pie can be found on just about any menu here, from dive bars to high-end bistros, and with good reason — the island’s eponymous pie is zesty, creamy, and delicious. Traditionally made from tangy key lime juice and a rich, sweet custard of egg yolk and condensed milk atop a crust, everybody from home cooks to renowned chefs has their own take on how it should be made. Try as many versions as you can while you’re here, and join in on the debate of cooked versus uncooked filling, graham cracker versus pie crust, and whipped cream versus meringue topping.

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