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.

Rental unit 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.
$295 per night
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Condo in Key West
Modern 2BR Condo Old Town/Balcony & Pool
Come enjoy this fully updated 2/BR condo in the heart of Old Town. The perfect balance of being close to all the action & far enough away to enjoy a quiet getaway. Get comfortable in this clean & comfy home, which offers two private balconies, updated kitchen & modern bath. Desirable Southard Square is surrounded by tranquil tropical gardens & a heated 20x40 pool. Centrally located, this condo is 4 blocks from Duval St, Seaport Historic Pier & a short walk or bike ride anywhere on the island!
$137 per night
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Rental unit in Key West
At Mine | Lovely Suite steps from Duval Street
Beautifully renovated boutique hotel unit 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.
$328 per night
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Stay near Key West's top sights

Photo of Southernmost Point of the Continental US
Southernmost Point of the Continental US64 locals recommend
Photo of Mallory Square
Mallory Square100 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!
$179 per night
Home in Key West
Home Away from Home with Free parking
$331 per night
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Home in Key West
Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
$491 per night
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Private room in Key West
Old Town - Room Opens to Pool and Garden
$286 per night
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Home in Key West
Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
$521 per night
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Home in Key West
Private 2BR with Pool in Old Town Key West
$350 per night
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Home in Key West
Caribbean Cottage - 2BR/2BA Sleeps 6, Heated Pools
$300 per night
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Home in Key West
Cottage in Paradise Old Town hot tub, dog-friendly
$282 per night
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Home in Key West
Relaxing Getaway - Duval Duplex - Free parking
$287 per night
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Home in Key West
Fully Remodeled Home in Downtown
$430 per night
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Home in Key West
Margarita Cottage-
$364 per night
Home in Key West
Robinson Crusoe Cottage- Shared Pool
$441 per night

Key West condo rentals

Condo in Key West
Duval Street Suite on Duval Free Parking and Pool
$421 per night
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Condo in Key West
Atlantic Ocean Studio
$154 per night
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Condo in Key West
Sky Loft - Penthouse, Shared Pool & Downtown!
$486 per night
Condo in Key West
Best Location in Old Town Key West
$250 per night
Condo in Key West
Ocean front 1BR/1BA Suite w/ kitchen & living rm
$199 per night
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Condo in Key West
La Dolce Vita, Old Town!Steps to Duval! 3 blks bch
$327 per night
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Condo in Key West
*Come to my Deck for a time you won't Forget!
$285 per night
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Condo in Key West
Perfect 2BR Waterview | Balcony | Pool
$289 per night
Condo in Key West
Duval Corner- Newly Renovated Condo steps to Duval
$398 per night
Condo in Key West
Key West Downtown Treasure #2
$364 per night
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Condo in Key West
Tropical 1BR | Pool | Hot Tub | Central AC | W/D
$227 per night
Condo in Key West
Condo 2 br, Balcony, Private covered parking
$428 per night
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Key West apartment rentals

Rental unit in Key West
Royal Palm- 1 Block to Duval with Grill & Hot Tub!
$418 per night
Rental unit in Key West
Honeymoon Hideaway, King bed, Private Deck & Spa!
$449 per night
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Rental unit in Key West
Red Room at Grand Maloney Hotel with Pool!
$432 per night
Rental unit in Key West
The Green House ❀ Garden
$387 per night
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Rental unit in Key West
Harvey`s Haven
$459 per night
Private room in Key West
Mallory House Room #2
$195 per night
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Rental unit in Key West
Deckside Suite Small Efficiency
$359 per night
Rental unit in Key West
Cozy and fully equipped Apartment with pool #1
$343 per night
Rental unit in Key West
Banana Split - Pool, Parking & Private Balcony!
$419 per night
Rental unit in Key West
Key West - Sunrise ❀ The Green House
$382 per night
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Rental unit in Key West
At Mine | Lovely Suite steps from Duval Street
$328 per night
Rental unit in Key West
Central location Studio 1st-Floor | Deck
$182 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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