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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.

Hotel room in Key West
The Sanchez House Room #3
There is no better welcome to Key West than staying in local and famous folk artist Mario Sanchez's birth home. This home was built in the 1860's in the heart of the historic Gato and Merrero cigar factory villages. Featuring original Dade County pine construction, and located right on historic Duval Street, the Sanchez House is guaranteed to offer the historic atmosphere and living a part of Key West many visitors want to experience. Sit on the balcony and enjoy the trade winds & Ocean Breeze.
Individual Host
SUPERHOST
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.
Individual Host
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Private room in Key West
Mallory House Room #2
There is no better place for your Key West stay than Mallory House. This historic circa 1890’s home is located on Duval Street in the Gato Cigar Factory Village. Mallory House is steps away from famous attractions, restaurants, cafés, bars and shops. Stay within close proximity to the Southernmost point and beach, the Hemingway house and lighthouse. Enjoy a complimentary cup of coffee on our spacious balcony overlooking world famous Duval Street.
Individual Host
SUPERHOST

Vacation rentals for every style

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Stay near Key West's top sights

Photo of Fort Zachary Taylor Historic State Park
Fort Zachary Taylor Historic State Park47 locals recommend
Photo of Harry S. Truman Little White House
Harry S. Truman Little White House27 locals recommend
Photo of Southernmost Point of the Continental US
Southernmost Point of the Continental US64 locals recommend
Photo of Higgs Beach
Higgs Beach21 locals recommend
Photo of Key West Butterfly and Nature Conservatory
Key West Butterfly and Nature Conservatory56 locals recommend
Photo of Mallory Square
Mallory Square100 locals recommend

Key West house rentals

Home in Key West
McCartney's Manor - Deluxe K Suite W/Pvt. Spa!
Individual Host
SUPERHOST
Home in Key West
Downtown Waterfront 2/2 Dock & Pool Pet-Friendly
Individual Host
SUPERHOST
Home in Key West
Private 2BR with Pool in Old Town Key West
Individual Host
SUPERHOST
Home in Key West
Lil' Bit- Updated Cottage In Quiet Neighborhood!
Professional Host
Private room in Key West
A Little Place in Key West
Individual Host
SUPERHOST
Private room in Key West
Old Town - Room Opens to Pool and Garden
Individual Host
SUPERHOST
Home in Key West
Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
Individual Host
SUPERHOST
Home in Key West
Home Away from Home with Free parking
SUPERHOST
Home in Key West
Relaxing Getaway - Duval Duplex - Free parking
SUPERHOST
Home in Key West
John Truman's Hideaway~ Walk to Duval Street from
Professional Host
Home in Key West
Mango Tree Cottage
Home in Key West
Casita de Catherine by AvantStay | Cute Cottage w/ Hot Tub and Spacious Patio, 1 Block to Duval St!
Professional Host

Key West beach vacation rentals

Hotel room in Key West
The Sanchez House Room #1
Individual Host
SUPERHOST
Rental unit in Key West
Duval Balcony - Street Suite
Individual Host
SUPERHOST
Rental unit in Key West
Key West - Sunrise ❀ The Green House
Professional Host
Rental unit in Key West
Key West - Sunset ❀ The Green House
Professional Host
Condo in Key West
Large waterfront 2/2 end unit with boat slip
Individual Host
SUPERHOST
Rental unit in Key West
Small furnished efficiency, walk to Duval St.
Individual Host
SUPERHOST
Rental unit in Key West
Duval Street Suite full kitchen Old Town with pool
SUPERHOST
Townhouse in Key West
Poolside Cottage #412
Professional Host
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Guest suite in Key West
Luxury King Loft (no kitchen)
Individual Host
SUPERHOST
Rental unit in Key West
Duval Balcony Spanky's Retreat
Individual Host
SUPERHOST
Rental unit in Key West
Queen Studio
Individual Host
Rental unit in Key West
At Mine | Lovely Suite steps from Duval Street
Individual Host
SUPERHOST

Key West condo rentals

Condo in Key West
Ocean Front Studio private Sandy Beach in Key West
Individual Host
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Condo in Key West
Ocean front 1BR/1BA Suite w/ kitchen & living rm
Individual Host
SUPERHOST
Condo in Key West
Hidden Beach unit 1 The Perfect Place to stay
Individual Host
SUPERHOST
Condo in Key West
Key West Studio a short walk from Higgs & Duval
Individual Host
Condo in Key West
The Island Suite @ KW vacation
Condo in Key West
Duval Corner- Newly Renovated Condo steps to Duval
Professional Host
Condo in Key West
Lovely 1 BR condo in the heart of Old Town
Condo in Key West
Duval Street Suite on Duval Free Parking and Pool
SUPERHOST
Condo in Key West
KeyWest Oceanfront Christmas Eve Sat Dec 17 to 24
Individual Host
Condo in Key West
Fully renovated 2/2 bath condo w/ shared pool!
Professional Host
SUPERHOST
Condo in Key West
La Dolce Vita, Old Town!Steps to Duval! 3 blks bch
Individual Host
SUPERHOST
Condo in Key West
Hidden Beach Duplex, Best Place in Key West
Individual Host
SUPERHOST

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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