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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.

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SUPERHOST
Entire rental unit · Key West
At Mine | Lovely Suite steps from Duval Street
Beautifully renovated boutique hotel suite steps from Duval Street. This property is situated on a quiet street and offers a private pool and peaceful accommodation for vacationers and business travelers. The unit features a comfortable Queen-sized bed, hangers, TV, and AC. Indulge in Key West's warm weather year-round. This special place is close to everything, making it easy to plan your visit.
$141 per night
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Hotel room · Key West
Cabana Inn King Room (A) with Free Breakfast
Private Single Room located in a Boutique Hotel ⍙ The Cabana Inn, in the Heart of Key West. ☼☼☼ Located just a block from Duval Street, our adult-only Key West inn is hidden amongst the shady trees to create a tranquil paradise. Do not forget about our FREE Happy Hour and FREE Breakfast!
$143 per night
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SUPERHOST
Entire rental unit · Key West
Location, Location, Location! Low Budget Vacation!
Location, location, location! This studio is 1 block off Duval St, with Mallory Square, Capt Tony’s, Hog's Breath and Sloppy Joe’s just steps away. You will walk out the door and be right in the action. No $25 Ubers needed here. The apartment is all yours, with a private entrance (keypad entry) and private bath. It has a fridge, micro, toaster oven, electric burner, Keurig, high speed internet and TV with Netflix, but you won’t be spending much time indoors!
$107 per night

Vacation rentals for every style

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Stay near Key West's top sights

Photo of Mallory Square
Mallory Square34 locals recommend
Photo of Southernmost Point of the Continental US
Southernmost Point of the Continental US27 locals recommend
Photo of Fort Zachary Taylor
Fort Zachary Taylor26 locals recommend
Photo of The Key West Butterfly and Nature Conservatory
The Key West Butterfly and Nature Conservatory36 locals recommend
Photo of Higgs Beach
Higgs Beach9 locals recommend
Photo of Truman Little White House
Truman Little White House8 locals recommend

Key West house rentals

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SUPERHOST
Private room · Key West
Old Town - Room Opens to Pool and Garden
$179 per night
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SUPERHOST
Entire home · Key West
Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
$307 per night
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SUPERHOST
Entire home · Key West
2/2 Fully Updated Old Town Waterfront Corner Condo
$218 per night
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SUPERHOST
Entire home · Key West
Private 2BR with Pool in Old Town Key West
$159 per night
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Entire home · Key West
Lil' Bit / Updated Cottage In Quiet Neighborhood!
$133 per night
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SUPERHOST
Entire home · Key West
Private Paradise with Heated Waterfall Pool
$256 per night
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Entire home · Key West
John Truman's Hideaway~ Walk to Duval Street from
$222 per night
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Entire home · Key West
Pure Bliss, 3 bedroom luxury home
$289 per night
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SUPERHOST
Entire home · Key West
Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
$334 per night
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SUPERHOST
Entire home · Key West
Casa Cristol - Family Friendly Classic KW Charm
$687 per night
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Entire home · Key West
Casita de Catherine by AvantStay | Cute Cottage w/ Hot Tub and Spacious Patio, 1 Block to Duval St!
$200 per night
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SUPERHOST
Entire home · Key West
Waterfront Penthouse sleeps 16 w/Pool & Boat Dock
$375 per night

Key West condo rentals

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SUPERHOST
Entire condo · Key West
WALK TO BEACH, MALLORY SQUARE, DUVAL STREET
$185 per night
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SUPERHOST
Entire condo · Key West
Ocean Front Studio private Sandy Beach in Key West
$405 per night
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Entire condo · Key West
Lovely 1 BR condo in the heart of Old Town
$140 per night
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SUPERHOST
Entire condo · Key West
True Paradise
$168 per night
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Entire condo · Key West
Key West Downtown Treasure #1
$204 per night
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SUPERHOST
Entire condo · Key West
Hidden Beach unit 1 The Perfect Place to stay
$468 per night
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SUPERHOST
Entire condo · Key West
The Island Suite
$295 per night
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Entire condo · Key West
Come to my Deck for a time you won’t forget!
$204 per night
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SUPERHOST
Entire condo · Key West
Ocean front 1BR/1BA Suite w/ kitchen & living rm
$421 per night
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SUPERHOST
Entire condo · Key West
Sailor's Sanctuary - A Renovated Condo in Key West
$132 per night
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Entire condo · Key West
Duval Corner- Newly Renovated Condo steps to Duval
$276 per night
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SUPERHOST
Entire condo · Key West
Key West Studio a short walk from Higgs & Duval
$102 per night

Key West cottage rentals

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SUPERHOST
Entire cottage · Little Torch Key
Waterfront Cozy Cottage with Boat Ramp & Dock!
$320 per night
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SUPERHOST
Entire cottage · Key West
Oasis in old town Key West - private heated pool!
$181 per night
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SUPERHOST
Entire cottage · Key West
Private Cottage House in Old Town Key West!
$89 per night
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Entire cottage · Key West
"Great Old Town Cottage on White Street!"
$105 per night
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Entire cottage · Key West
Tranquil Dog-friendly Getaway with Shared Pool, WiFi, & AC - Snowbirds Welcome
$477 per night
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SUPERHOST
Entire cottage · Cudjoe Key
ATLANTIS...Ocean Front Cottage Retreat!
$555 per night
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Entire cottage · Key West
The Dancing Rooster
$465 per night
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Entire cottage · Key West
Cozy Cottage with Porch, WiFI, AC, & Amazing Walking Locale - Small Dogs OK
$394 per night
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Entire cottage · Key West
1 bedroom Cottage
$594 per night
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SUPERHOST
Entire cottage · Key West
Pete's West Cottage steps from Duval
$361 per night
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SUPERHOST
Entire cottage · Key West
Namaste : A blissful one bedroom cottage designed with relaxation in mind.
$484 per night
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SUPERHOST
Entire cottage · Cudjoe Key
Turtle Cove Views at Venture Out - 2BR/2BA Cottage +35’ Private Slip | 80’ Pool…
$222 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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  4. Monroe County
  5. Key West