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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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Pelican Cottage

Small cottage on property. Perfect for a Month long Key West getaway.

G$31,381 per night
SUPERHOST
  1. Private room
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Nuns Room, A single travelers delight!

You won’t want to leave this charming, one-of-a-kind space specially designed for a single traveler. If either your here for fun or for business traveling alone should always be done in style. Enjoy this light and airy room with ice cold A/C and a bed designed for one. Two full bathrooms available for use also on our second floor that are shared with 3 other rooms across the hall. ONE GUEST ONLY.

G$28,333 per night
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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.

G$24,895 per night

Vacation rentals for every style

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Key West house rentals

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  2. Key West
Home Away from Home-Beautiful Duval Getaway
G$52,839 per night
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Mango Tree Cottage
G$27,197 per night
SUPERHOST
  1. Private room
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Old Town - Room Opens to Pool and Garden
G$61,716 per night
SUPERHOST
  1. Entire home
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Private 2BR with Pool in Old Town Key West
G$48,117 per night
  1. Entire home
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Live Like a Local in this Key West Conch Cottage
G$31,381 per night
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Airy & Bright Home with Pool in Old Town
G$49,163 per night
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Little Hemingway House Villa
G$47,071 per night
SUPERHOST
  1. Private room
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Sunny King suite Clawfoot tub patio sm Kitchen
G$64,584 per night
SUPERHOST
  1. Entire home
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Blu on White - Work or Home School from Paradise!
G$90,406 per night
  1. Entire home
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*Casa Amelia* Pet friendly, Monthly Old Town home
G$73,222 per night
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Gulf Getaway // Family Friendly Corner Home in Waterfront Truman Annex
G$48,684 per night
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Casa Cristol - Family Friendly Classic KW Charm
G$156,486 per night

Key West condo rentals

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Come to my Deck for a time you won’t forget!
G$44,718 per night
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Hidden Beach unit 1 The Perfect Place to stay
G$97,281 per night
SUPERHOST
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Sailor's Sanctuary - A Renovated Condo in Old Town
G$41,841 per night
  1. Entire condo
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Bright Condo with Homey Feel, Entertainment & Private Parking - Beach Nearby
G$46,653 per night
  1. Entire condo
  2. Key West
ENJOY THE BEST DEAL IN THE KEYS!!
G$47,071 per night
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  1. Entire condo
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Atlantic Ocean Studio
G$80,963 per night
  1. Entire condo
  2. Key West
Duval Corner // Newly renovated condo steps from Duval St!
G$60,463 per night
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  1. Entire condo
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Soak in the sun, relax, eat, drink and be merry
G$26,988 per night
  1. Entire condo
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2 BR Condo Banyan Tree, Key West,FL
G$73,013 per night
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Hidden Beach unit 2, The Perfect Place To Stay
G$99,074 per night
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The Island Suite
G$84,728 per night
  1. Entire condo
  2. Key West
Colorful beachfront condo w/ ocean view balcony & shared hot tub/pool/tennis!
G$75,942 per night

Key West apartment rentals

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Studio Condo w/ Entertainment, Full Kitchen & Private Parking - Central Location
G$33,264 per night
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Small furnished efficiency, walk to Duval St.
G$20,921 per night
SUPERHOST
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Bella Vita: 1B/1B Condo for 2 Just Steps off Duval
G$54,542 per night
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Studio Suite with Shared Hot Tubs, Patio, Kitchenette - Steps from Beach, Dogs OK
G$35,983 per night
SUPERHOST
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Historic First Floor Caroline St w/Pool Sleeps 3
G$16,736 per night
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Historic 1st Fl Caroline St - Shared Pool Sleeps 2
G$21,967 per night
SUPERHOST
  1. Private room
  2. Key West
Mallory House Room #1
G$39,301 per night
SUPERHOST
  1. Entire rental unit
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Old Town Studio Apartment • Walk Everywhere!
G$24,477 per night
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  2. Key West
Location, Location, Location! Cute and Convenient!
G$27,197 per night
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  2. Key West
Sugar Pie Suite // Light & Bright Efficiency Studio Just 1 Block From Duval St!
G$52,868 per night
SUPERHOST
  1. Entire rental unit
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Tropical Garden Oasis 2/2 Apartment In Old Town
G$20,921 per night
SUPERHOST
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Duval Balcony Spanky's Retreat
G$59,266 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.