Key West Vacation Rentals, Florida: house rentals & more

Select from 1324 houses, 300 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.

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Condo/Apartment

Find properties near top attractions in Key West

Duval Street

Find the best place to stay - Key West

For those who enjoy the pool over the beach, come relax poolside.

Ultimate Beach Adventure! Pool, Restaurant, Bar, Bike Rental, Gym,

Sleeps 3 · 1 bedroom · 1 bathroom

Comfortable units with 1 King bed with a balcony are available now!

You Found it! Key West Getaway! Oceanfront Pool, Onsite Dining, Bike Rental!

Sleeps 2 · 1 bedroom · 1 bathroom

PINEAPPLE COTTAGE ~ Adorable, Updated Cottage in Old Town with Heated Pool!

Sleeps 4 · 1 bedroom · 1 bathroom

Top rated rentals - Key West

Horse Conch is on the second floor of this complex.

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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?

Snap up your vacation property in Key West Historic District and you'll be in the heart of one of Key West's leading neighborhoods. Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens are two major attractions here that'll entertain you during your visit.

What is the most popular type of vacation rental accommodation in Key West?

Based on our research, houses are the most desirable property type in Key West. But naturally, everyone's idea of the perfect stay differs. Vrbo has vacation homes of all shapes and sizes, and we'll help you to find your perfect match.

How much does it cost to rent a vacation rental in Key West?

Length of stay, property type and season are some of the things that can influence the price of a vacation home. Simply enter your dates of travel to find your perfect fit. From cozy chalets to expansive villas, all Vrbo vacation rentals offer incredible value.

How much does it cost to rent a beach house in Key West?

When you travel and the style and size of the property will influence the cost of your beachside stay. Put in your Key West travel dates to see all your options on Vrbo. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use our filters to choose the amenities and features you want in your beach house.

Are there pet-friendly vacation rentals in Key West?

Yes. You can pick from 1,825 vacation rentals that cater to pets in Key West. Lots of our pet-friendly vacation rentals even come with an outdoor area for your four-legged friend to play around in, doggie beds, complimentary treats and proximity to parks or green space. Apply the "Pets allowed" filter to find your pawfect place on Vrbo.

Can I rent a house with a pool in Key West?

Mark the "pool" box in our filter tool and take your pick of 1,496 houses with private pools in Key West on Vrbo. Morning swim, sunset soak or midnight dip? How you spend your free time is up to you when your Vrbo vacation property boasts a swimming pool.

What are popular rental amenities in Key West?

Some of the most popular rental amenities people are searching for in Key West include mountain views, a lake view and a barbecue grill. Whether you're on the road with buddies, family or even pets, Vrbo vacation properties have the best amenities for chilling out with your loved ones.

Are there large group vacation rentals in Key West?

You can pick from 191 vacation properties in Key West that can host a group of 10 or more guests. Whether you're organizing time away with the family or an event like an anniversary, there's enough room to get your loved ones together under the same roof.

Are there vacation rentals in Key West that welcome kids?

Bring the entire group together for a fun-filled adventure in Key West at one of our 1,818 family-friendly vacation properties. Many of these stays offer amenities that are suitable for getaways with the kids, such as full kitchens, extra bedrooms and pools. Just check the "Properties good for families" filter box and choose your favorite.

What are the top attractions for families in Key West?

There are loads of amazing things to see and do with the family in Key West, including:

Smathers Beach
South Beach
Higgs Beach

Are there one-bedroom vacation rentals in Key West?

You can choose from 451 one-bedroom rentals in Key West. Whether you're searching for a townhouse or a cabin, our one-bedroom properties are just right if you don't require loads of space. One of the perks of having your own digs? You'll never need to share your vacation with strangers.

Can I find two-bedroom vacation rentals in Key West?

Take your pick of 670 two-bedroom vacation rentals in Key West. Settle the kids into the second room or fill it with a couple of your besties. There's a spot for whoever's fortunate enough to be coming along.