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 $199 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.
Top rated rentals — Key West
Destination guide

Explore scenic beauty from a Key West villa rental

The unique island city of Key West is one of the best vacation spots for Florida villa rentals. You can experience mile after mile of emerald waters and coral reefs as you drive the Overseas Highway along the Florida Keys archipelago to the farthest southern point that is Key West. You've never had a vacation getaway quite like Key West. This historic former pirate haven is one of the best spots for snorkeling and diving anywhere in Florida. If you love shrimp or crabs, you are in for a delicious treat thanks to the fresh seafood restaurants in Key West.

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 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.


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 1,776 vacation rentals around Key West. From 1,077 house rentals to 124 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What is the best area to stay when traveling to Key West?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Key West:

  • Old Town: 1,106 vacation rentals
  • Historic Seaport: 816 vacation rentals
  • Uptown - Upper Duval: 261 vacation rentals
  • Meadows: 599 vacation rentals
  • New Town: 397 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

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:

  • Southernmost Point: 1,568 vacation rentals
  • Florida Keys National Marine Sanctuary: 1,568 vacation rentals
  • Fort Zachary Taylor Historic State Park: 1,567 vacation rentals
  • Schooner Western Union: 1,569 vacation rentals
  • Mallory Square: 1,569 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 1,077 Houses in Key West. Our other popular types of vacation rentals in Key West include:

  • Cottages: 124 rentals available
  • Bungalows: 124 rentals available
  • Condos/Apartments: 518 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 1,425 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

    Old Town
    1,106 vacation rentals
    Historic Seaport
    816 vacation rentals
    Uptown - Upper Duval
    261 vacation rentals
    599 vacation rentals
    New Town
    397 vacation rentals
    Truman Annex
    862 vacation rentals
    White Street Gallery District
    698 vacation rentals
    Bahama Village
    536 vacation rentals
    Sunset Key
    194 vacation rentals
    1,266 vacation rentals
    The Meadows
    623 vacation rentals
    617 vacation rentals
    Key West Historic District
    1,129 vacation rentals
    White St. Gallery
    683 vacation rentals