Discover a selection of 2,000 vacation rentals in Key West that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $90 per night, and houses and cottages are popular options for a stay in Key West. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Key West
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Destination guide

Book luxury vacation homes in Key West

Key West is one of the most popular places for luxury rentals in the Florida Keys. One of its highlights is The Ernest Hemingway Home and Museum, which is the former residence of the famous author. You could also visit the landmark for the southernmost point in the continental U.S. or check out Duval Street, a thrilling area filled with unique shops, waterfront dining, and lively bars. For more shopping, Mallory Square is a plaza with boutiques and shops offering a variety of goods and souvenirs. Key West also features an abundance of outdoor activities, such as surfing, diving, snorkeling, hiking, biking, and nature walks to see native wildlife.

Things to do

Admire local talent at Studios of Key West

Free-spirited Key West has long been a haven for artists and creatives. There's no better place to discover the scene than The Studios of Key West, a 3-story space showcasing works from local artists. Continue the theme at Hemingway House, a handsome Spanish Colonial estate that was once a sanctuary for the American novelist. If you want to meet one of Key West's most passionate eco-activists, head to Nancy Forrester's Secret Garden. From chirpy parrots to multicolored macaws, this backyard oasis offers a unique opportunity to get up close and personal with exotic Floridian birds.

Activities

Activities near Key West vacation homes

As the sun starts to set, Mallory Square gears up for a night of family-friendly fun. It's essentially one big street party, with fire breathers, tightrope walking dogs, tumbling acrobats and more. You'll also find plenty of action on Duval Street, a lively strip lined with neon-lit bars, theaters, galleries and boutiques. For a quieter scene, why not retreat to the deck of your Key West vacation rental villa for fruity Rum Runner cocktails and Floridian sunsets? For more action, you can snorkel at coral reefs, kayak in crystal-clear water, swim with dolphins, sail on catamarans and more.

Weather

Catch Key West's Fantasy Fest celebrations

Craving a dose of winter sunshine? Escape to Key West vacation rentals and you'll find yourself immersed in a tightknit community of locals. Chances are you'll soon be sharing key lime pie with your new neighbors. Locals cite spring as a Key West sweet spot. Crowds taper off and temperatures continue to hover around the 80s. Visit in the last week of October and you'll catch Key West's raucous Fantasy Fest celebrations. The 10-day street party sees the island come alive with pet parades, burlesque shows, costumed events, street food stalls and more.

Natural features

Pet-friendly vacations in Key West

With a footprint measuring in at just 7 square miles, Key West feels wonderfully intimate. It's part of the Florida Keys archipelago and sits just 90 miles from Cuba. You can find out more about the low-lying archipelago at the Florida Keys Eco-Discovery Center, a family-friendly learning space filled with interactive displays and rainbow-colored sea creatures. traveling with Fido? No problem. Floridians love their furry friends, which means you'll find plenty of pet-friendly Key West vacation rentals.

How to get there

How to get to and around Key West

Fly into Key West, FL (EYW-Key West Intl.), the closest airport, located 9.1 mi (14.6 km) from the city center.

How many vacation rentals are available around Key West?

Our 2021 property listings offer a large selection of 1,904 vacation rentals around Key West. From 990 house rentals to 114 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Explore destinations around Key West

Old Town Key West
1,160 vacation rentals
Historic Seaport
811 vacation rentals
Uptown - Upper Duval
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Meadows
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New Town
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Truman Annex
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White Street Gallery District
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Sunset Key
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Midtown
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The Meadows
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Downtown Key West
642 vacation rentals
Key West Historic District
1,179 vacation rentals
White St. Gallery
699 vacation rentals