Discover a selection of 2,000 vacation rentals in Key West, FL 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 $115 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, FL?

Our 2021 property listings offer a large selection of 2,101 vacation rentals around Key West. From 1,008 house rentals to 104 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the popular point of interests near where I can stay when traveling to Key West?

Vrbo offers a large selection of vacation rentals near lovely places in Key West. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Key West Golf Club: 2,064 vacation rentals
  • Mallory Square: 1,873 vacation rentals
  • Florida Keys National Marine Sanctuary: 1,876 vacation rentals
  • Harry S. Truman Little White House: 1,877 vacation rentals
  • Mel Fisher Maritime Museum: 1,877 vacation rentals

But there are many other points of interest around Key West listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Key West?

Yes, of course. Vrbo has 1,008 Houses in Key West. Our other popular types of vacation rentals in Key West include:

  • Cottages: 104 rentals available
  • Bungalows: 104 rentals available
  • Condos/Apartments: 693 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Villas and more.

Can I find a vacation rental with pool in Key West?

Yes, you can select your preferred vacation rental with pool among our 1,640 vacation rentals with pool available in Key West. Please use our search bar to access the selection of vacation rentals available.

Explore destinations around Key West

Key West Golf Club
2,064 vacation rentals
Mallory Square
1,873 vacation rentals
Florida Keys National Marine Sanctuary
1,876 vacation rentals
Harry S. Truman Little White House
1,877 vacation rentals
Mel Fisher Maritime Museum
1,877 vacation rentals
Florida Keys Eco-Discovery Center
1,876 vacation rentals
Nancy Forrester's Secret Garden
1,874 vacation rentals
Key West Tropical Forest and Botanical Garden
2,058 vacation rentals
Key West Wildlife Center
1,884 vacation rentals
Schooner Western Union
1,878 vacation rentals
Key West Aquarium
1,877 vacation rentals
Florida Keys Eco - Discovery Center
1,876 vacation rentals
Flagler Station Oversea Railway Historeum
1,876 vacation rentals
MLK Community Pool & Community Center
1,878 vacation rentals
Fort East Martello Museum and Gallery
2,059 vacation rentals
Key West Shipwreck Museum
1,877 vacation rentals
Key West Museum of Art and History
1,876 vacation rentals
Key West Cemetery
1,878 vacation rentals
Custom House Museum
1,876 vacation rentals
Studios of Key West
1,880 vacation rentals