Key West Vacation Rentals

Compare 145 vacation rentals.
USA > Florida > Key West

Make Key West your next getaway

Grab a Key West beach house or condo rental and experience the Sunshine State’s captivating tropical oasis. Here, at the southernmost point of the United States, turquoise Gulf of Mexico waters lap against sparkling white-sand beaches, promising ample opportunities for relaxation and adventure. Snorkel among vibrant coral reefs, hang up a hammock beside soothing ocean views, and treat yourself to a slice of famous Key lime pie on your next Florida vacation.

Explore Key West condo rentals, house rentals, studios, and more


Condo rentals

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House rentals

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View 9 Studios

Popular amenities for Key West vacation rentals

Dog-friendly Hot tub Internet
Wahoo Way On Duval
1 Bedroom | 1 Bath | Sleeps 2

Wahoo Way On Duval - Key West, FL

$192 avg / night
Pelican Suite
1 Bedroom | 1 Bath | Sleeps 4

Pelican Suite - Key West, FL

$355 avg / night
Osprey Suite
1 Bedroom | 1 Bath | Sleeps 4

Osprey Suite - Key West, FL

$329 avg / night
Yellowfin Ledge On Duval
1 Bedroom | 1 Bath | Sleeps 3

Yellowfin Ledge On Duval - Key West, FL

$311 avg / night
Sunrise Suites - Tierra Bomba Suite 403
2 Bedroom | 2 Bath | Sleeps 6

Sunrise Suites - Tierra Bomba Suite 403 - Key West, FL

$379 avg / night

View 140 more homes

Recent Key West guest reviews

Very cute and quaint. Pool was awesome! Perfect place for my husband and I. We stayed in the studio and our kids and their friends stayed in the main house. Worked out perfect. Thank you!
Sheryl M. | Jul 2024
Great location, next to Duval st
Timothy L. | Jul 2024
I love the location in relation to downtown. It is out of the way of all the madness but close enough to go right into it. I love the size of the unit. Perfect fit for 5. Having a full kitchen is amazing so we can cook some meals and avoid spending too much money on food and use it for other fun activities
Zach B. | Jul 2024
Key West vacation rental FAQ

Yes, 76 of our Key West homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 155 of our Key West vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >

Some of the most popular amenities in our Key West vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Key West team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Key West, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

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24/7 guest service
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Seamless check-in
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Professional cleaning

Explore our Key West, FL, vacation rentals

With a mix of island charm, thrilling water sports, and unforgettable experiences, Key West vacation rentals offer a getaway you’ll want to return to again and again. The island, the southernmost of the Florida Keys, boasts a rich history, with attractions like the Ernest Hemingway Home and Museum, the Harry S. Truman Little White House, and the Historic Key West District. Tour through the 187 historic buildings or hit the beach for one of the island’s main attractions: water sports.

Key West is a water sports enthusiast's dream, with the perfect backdrop for fishing, snorkeling, diving, paddleboarding, and more. It's also a gateway to the Dry Tortugas National Park, a remote and pristine island group accessible by seaplane and the popular Yankee Freedom ship. Back on land, be sure to explore the town and its must-see spots, like Duval Street’s lively mix of bars, restaurants, shops, and entertainment venues, as well as Smathers Beach and Fort Zachary Taylor State Park.

Where is Key West, FL?

Key West is located in the southernmost part of Florida, USA. It is an island city situated at the southern tip of the Florida Keys archipelago, and it is approximately 90 miles north of Cuba. It is connected to the mainland of Florida by the Overseas Highway, a scenic road that stretches across numerous islands of the Florida Keys.

Things to do in Key West, FL

Kick back on island time with a Key West vacation home and immerse yourself in a world of rich history, delicious cuisine, and beach fun. 

Does Vacasa offer snowbird or long-term rentals in Key West?

Yes, Vacasa has plenty of long-term, monthly, and snowbird rentals in Key West and throughout Florida. Stay close to the beach with an oceanfront beach house rental, resort condo rental, or vacation home with plenty of room for you and your crew. Find amenities like boat docks and slips, direct beach access, tennis courts, and outdoor pools.

Book a Key West house rental, condo, or cottage

Whether you're seeking adventure, relaxation, or a taste of Key West's famous Key lime pie, this island paradise offers a memorable vacation experience for travelers of all kinds. So, pack your flip-flops, grab your sunglasses, and get ready to savor the magic of Key West, where every day feels like a vacation in paradise. Find your perfect Key West vacation rental.

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