Key West vacation rentals

We found 2,421 vacation rentals — enter your dates for availability

Select from 1283 houses, 296 apartments, and other vacation rentals to find the perfect place for your stay in Key West. Whether you’re staying in a vacation home with family, friends, or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, such as parking and air conditioning. Whatever you're looking for, you'll find a rental for everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Key West

Showing deals for:Jul 11 - Jul 18

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.

 

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.

Splash-happy in Key West

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.

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.

Transportation to and around Key West

Fly into Key West Intl. Airport (EYW), the closest airport, located 3 mi (4.8 km) from the city center.

Frequently asked questions

What is the best area to stay in Key West when booking a vacation rental?
Make a booking for a vacation property in Old Town Key West and experience one of Key West’s most popular areas. South Beach and Simonton Beach are much-loved attractions here that’ll entertain you during your visit.
What is the most popular type of vacation rental accommodation in Key West?
The most in-demand types of vacation rentals in Key West are condos. Looking for something different? Vrbo has a variety of options to match the needs of our guests, so you’ll see vacation properties in all shapes and sizes. The perfect home away from home is waiting for you — grab yours today.
How much does it cost to rent a vacation rental in Key West?
A range of things can determine how much you pay for a vacation rental in Key West, like the season, length of stay and type of property. But, all of our vacation homes have one thing in common — incredible value. Simply enter your travel dates to find your ideal match.
How much does it cost to rent a beach house in Key West?
Prices for beach houses in Key West vary depending on the style and size of the property and when you’re traveling. Just enter your travel dates into Vrbo and the number of guests to view available options and prices. From there you can use our filters to tailor your search results by ratings, amenities and more.
Are there pet-friendly vacation rentals in Key West?
Pack a squeezy toy and a bone for your beloved pooch because Key West has 1,755 properties that throw out the welcome mat to pets. Let your four-legged pal get in on the family fun at one of our pet-friendly vacation rentals on Vrbo. Simply enter your destination and travel dates, then check the “Pets allowed” filter box.
Can I rent a house with a pool in Key West?
Dig out your swimsuit and inflatable swan, because there are 1,432 houses with a private pool in Key West. Kick back at one of these sought-after vacation homes and you’ll enjoy pool days every day. Simply enter your travel dates into Vrbo, then use the “pool” filter to find the perfect place for a splashing good time!
Are there vacation rentals in Key West that welcome kids?
With 1,733 family-friendly vacation properties to pick from in Key West, now is a superb time to introduce your kids to the pleasures of travel. Click on our “Properties good for families” filter to look for stays that feature conveniences perfect for families on the move, like full kitchens, backyards, hot tubs and bunk beds.
What are the top attractions for families in Key West?
Keeping the kids occupied during your vacation in Key West is simple with these family-friendly attractions:

  • Duval Street
  • Clarence S. Higgs Memorial Beach Park
  • Nancy Forrester’s Secret Garden

Are there vacation rentals with WiFi in Key West?
Key West has 718 vacation rentals with WiFi, so you can stay connected while you’re away. Simply check the “WiFi” box in our handy search filter to find the perfect property. From streaming Hollywood blockbusters to writing and sending emails, these Vrbo homes make it a breeze to get online.
How can I find vacation rentals with air conditioning in Key West?
Pick your dates and then use our filter tool to look for vacation rentals with air conditioning in Key West on Vrbo. With 1,697 air-conditioned properties to choose from here, you can look forward to a cool and comfy stay.
How old do you have to be to rent a vacation rental in Key West?
The minimum required age is usually 16, 18 or 21. It can vary across properties on Vrbo, so check the rules of your chosen Key West vacation rental before booking your stay.
How long can I rent a vacation rental in Key West for?
It’s really down to the Key West property. To see all available options offering extended stays, just enter your travel dates and number of guests into the Vrbo search page. You can enjoy having the entire place to yourself, as well as amenities such as a fully-equipped kitchen, air conditioning and an outdoor space where the kids can run and play. Be on the lookout for long-term stays that offer weekly or monthly discounts.
Does Vrbo offer discounts for vacation homes in Key West?
Whether you’ve got your eye on one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you’re sure to score some incredible deals and discounts on Vrbo. From mini stays to extended vacations, we’ve got the perfect space for your next Key West escape.

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