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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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  1. Entire condo
  2. Key West
Key West Studio a short walk from Higgs & Duval

This clean, cozy studio is located in old town, just a 10 minute walk to Higgs Beach and a 15 minute walk to Duval St. Grab a bike from the local shop next door and explore all Key West has to offer. You are close to all the great local restaurants and shops. There is also a full kitchen if you prefer to cook at home. The grill out back in the garden is perfect for a BBQ. There is snorkeling, boat tours, fishing, and water sports nearby.

ﺩ.ﺇ227 per night
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At Mine | Key West 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 A/C. Indulge in Key West's warm weather year-round. This special place is close to everything, making it easy to plan your visit.

ﺩ.ﺇ403 per night
  1. Private room
  2. Key West
Steps off Duval - Malaga - Beautiful Queen Room with private patio, INCLUDED IN THE PRICE: breakfast, happy hour, bicycles & parking.

One of 6 rooms at Andrews Inn! Neighbor with the Hemingway House, a beautifully decorated room with private bathroom. New AC, tower fan, a new queen-size NECTAR mattress, private little patio, desk, Smart TV with Netflix, free Wi-Fi, coffee machine, in-room refrigerator. We are an owner-operated Guest House where you will feel a lovely welcoming and a relaxing atmosphere. Included in the price: breakfast, happy hour, bicycles & parking. Best location in Key West!

ﺩ.ﺇ808 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 Fort Zachary Taylor
Fort Zachary Taylor25 locals recommend
Photo of The Key West Butterfly and Nature Conservatory
The Key West Butterfly and Nature Conservatory37 locals recommend
Photo of Southernmost Point of the Continental US
Southernmost Point of the Continental US26 locals recommend
Photo of Truman Little White House
Truman Little White House8 locals recommend
Photo of Higgs Beach
Higgs Beach9 locals recommend

Key West house rentals

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  2. Key West
A Little Place in Key West
ﺩ.ﺇ526 per night
  1. Entire home
  2. Key West
Mango Tree Cottage
ﺩ.ﺇ478 per night
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Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
ﺩ.ﺇ1,063 per night
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Home Away from Home-Beautiful Duval Getaway
ﺩ.ﺇ852 per night
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Private 2BR with Pool in Old Town Key West
ﺩ.ﺇ716 per night
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Relaxing Getaway - Duval Duplex - Free parking
ﺩ.ﺇ897 per night
  1. Entire home
  2. Key West
Entire home, dog friendly, yard, hot tub, parking
ﺩ.ﺇ437 per night
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  2. Key West
Hydration Station - Single Family home in Old Town
ﺩ.ﺇ551 per night
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Airy & Bright Home with Pool in Old Town
ﺩ.ﺇ632 per night
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Little Mermaid
ﺩ.ﺇ900 per night
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Private Paradise with Heated Waterfall Pool
ﺩ.ﺇ588 per night
  1. Entire home
  2. Key West
Live Like a Local in this Key West Conch Cottage
ﺩ.ﺇ551 per night

Key West cottage rentals

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Private Cottage House in Old Town Key West!
ﺩ.ﺇ433 per night
  1. Entire cottage
  2. Key West
"Great Old Town Cottage on White Street!"
ﺩ.ﺇ478 per night
  1. Entire cottage
  2. Key West
1 bedroom Cottage
ﺩ.ﺇ896 per night
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Oasis in old town Key West - private heated pool!
ﺩ.ﺇ441 per night
  1. Entire cottage
  2. Key West
Cozy Cottage with Porch, WiFI, AC, & Amazing Walking Locale - Small Dogs OK
ﺩ.ﺇ1,447 per night
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**CASA SERENDIPITY @ OLD TOWN** Historic 3BR/2BA Home & Pool + LAST KEY SERVICES...
ﺩ.ﺇ1,466 per night
  1. Entire cottage
  2. Key West
Tranquil Dog-friendly Getaway with Shared Pool, WiFi, & AC - Snowbirds Welcome
ﺩ.ﺇ2,009 per night
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The Sunshine House, Best Location in Key West!
ﺩ.ﺇ588 per night
  1. Entire cottage
  2. Key West
The Dancing Rooster
ﺩ.ﺇ1,805 per night
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  2. Key West
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
ﺩ.ﺇ1,671 per night
  1. Entire cottage
  2. Key West
A Touch of Bermuda in Key West
ﺩ.ﺇ1,322 per night
  1. Entire cottage
  2. Key West
Colorful Cottage w/Shared Pool, Central AC, WiFi, Washer/Dryer - Dog-Friendly!
ﺩ.ﺇ500 per night

Key West condo rentals

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Hidden Beach unit 1 The Perfect Place to stay
ﺩ.ﺇ1,561 per night
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Sailor's Sanctuary - A Renovated Condo in Key West
ﺩ.ﺇ446 per night
  1. Entire condo
  2. Key West
New listing! Inviting condo with a private deck and shared swimming pool
ﺩ.ﺇ566 per night
  1. Entire condo
  2. Key West
Come to my Deck for a time you won’t forget!
ﺩ.ﺇ715 per night
  1. Entire condo
  2. Key West
Lovely 1 BR condo in the heart of Old Town
ﺩ.ﺇ441 per night
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Ocean front 1BR/1BA Suite w/ kitchen & living rm
ﺩ.ﺇ1,546 per night
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  2. Key West
WALK TO BEACH, MALLORY SQUARE, DUVAL STREET
ﺩ.ﺇ695 per night
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  1. Entire condo
  2. Key West
Ocean Front Studio private Sandy Beach in Key West
ﺩ.ﺇ1,488 per night
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True Paradise
ﺩ.ﺇ661 per night
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The Island Suite
ﺩ.ﺇ1,017 per night
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Old Town condo w/pool, Frances St.
ﺩ.ﺇ547 per night
  1. Entire condo
  2. Key West
Bohemian Breeze @ Truman Annex
ﺩ.ﺇ893 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.

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Key West