Destination guide

Paradise at Key West vacation home rentals

Covering a tiny footprint, you'll quickly feel at home in Key West. It never fails to enchant with colorful Caribbean homes, milky white moonflowers and an eccentric population of locals. As you get to know the island, you'll stumble across bohemian cafes filled with tropical plants, breezy seafood restaurants and "salty dog" bars that serve up ice cold beer and live music. Whether you're holidaying with friends, family or even flying solo, Key West vacation rentals unlock access to this quirky slice of Florida.

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.

Can I find a vacation rental around Key West?

Yes, our 2019 property listings offer a large selection of 1,747 vacation rentals near Key West. From 789 Houses to 530 Condos/Apartments, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Key West for a holiday or a weekend are on HomeAway.

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: 1,092 vacation rentals
  • Truman Annex: 859 vacation rentals
  • Uptown/Upper Duval: 258 vacation rentals
  • Bahama Village: 544 vacation rentals
  • Historic Seaport: 816 vacation rentals

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

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

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

  • South Beach: 1,565 vacation rentals
  • Southernmost Point: 1,564 vacation rentals
  • Red Barn Theater: 1,564 vacation rentals
  • Mallory Square: 1,565 vacation rentals
  • Fort Zachary Taylor Historic State Park: 1,562 vacation rentals

But there are many other points of interest around Key West listed on HomeAway 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. HomeAway has 789 Houses in Key West. Our other popular types of vacation rentals in Key West include:

  • Condos/Apartments: 530 rentals available
  • Cottages: 119 rentals available
  • Bungalows: 119 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 1,375 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
    1,092 vacation rentals
    Truman Annex
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    Uptown/Upper Duval
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    Bahama Village
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