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Key West vacation rentals

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Top-rated vacation rentals in Key West

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Garden House Cozy King Room

One-of-a-kind place accommodations in the heart of Old Town. These rooms feature one queen bed that can accommodate up to two people. Our Adults Only accommodations come complete with a quaint swimming pool and spa, in addition to, a free continental breakfast served daily.

$273 per night
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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.

$107 per night
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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.

$175 per night

Vacation rentals for every style

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Key West house rentals

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Mango Tree Cottage
$130 per night
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A Little Place in Key West
$156 per night
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*Casa Amelia* Pet friendly, Monthly Old Town home
$350 per night
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Home Away from Home-Beautiful Duval Getaway
$248 per night
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Private 2BR with Pool in Old Town Key West
$230 per night
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Live Like a Local in this Key West Conch Cottage
$150 per night
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Paradise Palms
$315 per night
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Old Town - Room Opens to Pool and Garden
$295 per night
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The Eagle’s Nest (w/ heated pool)
$192 per night
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Airy & Bright Home with Pool in Old Town
$235 per night
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Little Hemingway House Villa
$225 per night
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Private Paradise with Heated Waterfall Pool
$257 per night

Key West condo rentals

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Come to my Deck for a time you won’t forget!
$216 per night
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Ocean front 1BR/1BA Suite w/ kitchen & living rm
$521 per night
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Hidden Beach unit 1 The Perfect Place to stay
$465 per night
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Atlantic Ocean Studio
$387 per night
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2 BR Condo Banyan Tree, Key West,FL
$349 per night
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Key West Studio a short walk from Higgs & Duval
$118 per night
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Beautiful Condo with Deck, Patio, & Pool - Walk to Duval Street & Beaches
$283 per night
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Sky Loft On Southard // Immaculate Condo In Perfect Location w/ Shared Pool
$384 per night
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Bright Condo with Homey Feel, Entertainment & Private Parking - Beach Nearby
$206 per night
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**CIELO AZUL @ THE BEACH CLUB** Oceanfront Condo / Pools + LAST KEY SERVICES...
$270 per night
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Duval Corner // Newly renovated condo steps from Duval St!
$283 per night
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Sailor's Sanctuary - A Renovated Condo in Old Town
$200 per night

Key West apartment rentals

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Bella Vita: 1B/1B Condo for 2 Just Steps off Duval
$275 per night
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Studio Suite with Shared Hot Tubs, Patio, Kitchenette - Steps from Beach, Dogs OK
$173 per night
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Studio Condo w/ Entertainment, Full Kitchen & Private Parking - Central Location
$159 per night
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Historic First Floor Caroline St w/Pool Sleeps 3
$80 per night
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Mango Hideaway steps off World Famous Duval street
$382 per night
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Tropical Garden Oasis 2/2 Apartment In Old Town
$100 per night
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Luxurious upstairs apartment with pool #3
$300 per night
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Duval Balcony Spanky's Retreat
$248 per night
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Key west in town studio with free bikes
$224 per night
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Oceanbreeze Cottage
$130 per night
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Old Town Studio Apartment • Walk Everywhere!
$117 per night
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Duval Balcony - Street Suite
$279 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.


How do I get around Key West?

Air travelers can fly straight into Key West International Airport (EYW), from which point you can hop on a shuttle bus to get to the center of town, or rent a car to drive to your vacation rental. You could also fly into Miami International Airport (MIA) or Fort Lauderdale-Hollywood International Airport (FLL), and grab the Key West shuttle bus from either, directly to your destination. By land, you’re looking at around a four-hour drive from Miami, or less than five-hours drive from Fort Lauderdale. Once settled at your Key West house rental, you won’t need a car; most people prefer to soak up the lively atmosphere on foot, bike, scooter, or golf cart (all of which are available to rent on the island).


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.