Key West Vacation Rentals

Compare 153 vacation rentals.
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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.

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Condo rentals

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House rentals

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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

$276 avg / night
Pelican Suite
1 Bedroom | 1 Bath | Sleeps 4

Pelican Suite - Key West, FL

$382 avg / night
Osprey Suite
1 Bedroom | 1 Bath | Sleeps 4

Osprey Suite - Key West, FL

$348 avg / night
Yellowfin Ledge On Duval
1 Bedroom | 1 Bath | Sleeps 3

Yellowfin Ledge On Duval - Key West, FL

$262 avg / night
Sunrise Suites - Tierra Bomba Suite 403
2 Bedroom | 2 Bath | Sleeps 6

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

$414 avg / night

View 148 more homes

Recent Key West guest reviews

The location was perfect. We rented bikes through Eaton and the location of the apartment was within a short walk or bike ride. Having a parking space was such an amenity in that area as well. The place itself was cute and clean. We loved the shower and the sitting room.
Erica M. | May 2024
I have rented many homes over the years. This one stood out for cleanliness in particular: first off it was just CLEAN. Even the fridge, inside and out. They don’t even leave prior customers’ belongings behind which I have seen at all other rentals (ie, mustard in the fridge, shampoo in bathroom, etc). They also provided hotel-style bathroom toiletries, and some basic coffee supplies and a sample of laundry soap if you choose to use the washing machine. Then the whole atmosphere: what a great, quiet little cottage! We had our own private pool 😍. We were a couple staying for our 30th wedding anniversary - it was PERFECT. So much privacy all the way around the backyard/pool, but also the front porch which had a high fence for privacy! Tips if you choose this place (and I highly recommend you do): the listing may already say this, but there is a full bathroom and bedroom on the bottom floor. That bedroom has 2 twin beds and its own tv. The upstairs bedroom had a king size bed (May 2024) and another full bath (and its own tv). Both bathrooms are spacious, especially the showers. The upstairs bedroom is in a room (you can see it in the listing photos) that have an angled ceiling, so depending on your height you may have a little extra work getting in or out of bed. It didn’t bother us, but we are average height. Also, Vacasa provided a few beach-sized towels for the pool. Even though it’s a few streets away from Duval, it is a quiet area. Can’t stress this enough - if you want to be steps away from the party atmosphere on Duval but need your rest LOL, this is a great place! They do have “quiet hours” listed so look into that before you book if it’s important to you. We stayed during a very hot time - the AC and ceiling fans all worked great and kept us cool. House was well insulated: we didn’t hear the roosters hardly at all from the upstairs bedroom. It has a metal roof so rain will be a little louder up in that upstairs bedroom: we found the sound of rain to be very relaxing! Would definitely book this place again!
Reba J. | May 2024
Been there 4 times love to come back
GARY T. | May 2024
Key West vacation rental FAQ

Yes, 84 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. 165 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.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
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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