Key West Vacation Rentals

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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, apartments, and more

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Condo rentals

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House rentals

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Apartments

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Popular amenities for Key West vacation rentals

Popular
Dog-friendly Hot tub Internet
Sunrise Suites - Panama Suite 310
2 Bedroom | 2 Bath | Sleeps 6

Sunrise Suites - Panama Suite 310 - Key West, FL

$407 avg / night
(excludes fees and taxes)
4.51 (140)
Truman Suite #3
0 Bedroom | 1 Bath | Sleeps 2

Truman Suite #3 - Key West, FL

$286 avg / night
(excludes fees and taxes)
4.32 (160)
Sunrise Suites - Tierra Bomba Suite 403
2 Bedroom | 2 Bath | Sleeps 6

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

$429 avg / night
(excludes fees and taxes)
3.94 (89)
Amelia House
3 Bedroom | 2 Bath | Sleeps 8

Amelia House - Key West, FL

$854 avg / night
(excludes fees and taxes)
4.33 (112)
Sunrise Suites - Cozumel Suite 112
2 Bedroom | 2 Bath | Sleeps 6

Sunrise Suites - Cozumel Suite 112 - Key West, FL

$414 avg / night
(excludes fees and taxes)
4.31 (122)

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Recent Key West guest reviews

Airplanes landing, taking off and overhead weren't really an issue even tho we could see the airport from our balcony. Love the quiet back corner we were in and covered parking was nice too. The pool looked nice ~ perhaps a bit shady? We were too short a stay to get to use it. Not sure how easy it would work for getting around if you didn't have a car of your own ~ pretty far walk from anywhere and bus routes don't come here. Vacasa was great about pre-check-in communications but dropped the ball on the check out. Turns out you're not checked out until you complete their text link ~ but we didn't know that, so by the time we looked at their text (half an hour later) we had been checked out and left the island ~ we're stressing that they'll try to charge us a late check out fee. They never let us know this is their system. VERY frustrating way to end our Key West stay. Also, on our last night we did laundry and were unpleasantly surprised that there was something nasty left in the empty washer ~ it stunk and was filthy disgusting. Otherwise the place was clean, spacious and just what we needed. Just don't rent this place thinking you're going to have an easy walk to the happening areas.
Karen S. | May 2025
We stayed at this house for three nights and loved it! It’s a courtyard with several units that is very well maintained, as is this home. Everything was in great shape and we had all of the linens and supplies need for our trip. Aside from the refrigerator, we did not use any kitchen appliances or supplies. Both the bedroom and living/dining room area had plenty of room and were well furnished. All communication with the rental company was via text and email, but we did not have any issues requiring us to communicate aside from check in & out instructions. The location was perfect - just far enough away from the noise of Duval, but easy to get around by foot, bike or car. We were lucky enough to get a street parking spot right outside the gate and left the car there for the entire stay. We would definitely stay here again and would recommend this home to other couples.
Sean F. | May 2025
We've stayed at several Truman Annex homes and this one stands out. Beside the perfect location, quick walk to Mallory Square area, and to Eaton, it is spacious and the pool is very close. We would stay there again.
Phil M. | May 2025
Key West vacation rental FAQ

Yes, 47 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. 112 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 the 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 problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Key West, log in to Trip Manager to explore the options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
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.

Explore long-term rentals in Key West > 

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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