Key West Vacation Rentals

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USA > Florida > Key West

Make Key West your next getaway—choose from 165 great vacation rentals

For an island that is only two miles long and four miles wide, you'd think it would be a quiet place, demanding long trips outside the immediate area to reach attractions, good food, and historical sites. However, that's far from the case when you book one of our Key West vacation rentals! With a vibrant arts culture, a variety of opportunities for outdoor adventures, and a welcoming small-town attitude, Key West promises a unique and memorable beach vacation. 

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

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Condo rentals

View 80 Condo rentals
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House rentals

View 46 House rentals
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Studios

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Key West vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Sunrise Suites - Saint Croix Suite 212
2 Bedroom | 2 Bath | Sleeps 6

Sunrise Suites - Saint Croix Suite 212 - Key West, FL

$348 avg / night
Sunrise Suites - Tierra Bomba Suite 403
2 Bedroom | 2 Bath | Sleeps 6

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

$344 avg / night
Sunrise Suites - Catalina Suite 311
2 Bedroom | 2 Bath | Sleeps 6

Sunrise Suites - Catalina Suite 311 - Key West, FL

$340 avg / night
Sunrise Suites - Jamaica Suite 102
2 Bedroom | 2 Bath | Sleeps 6

Sunrise Suites - Jamaica Suite 102 - Key West, FL

$333 avg / night
Sunrise Suites - Bonaire Suite 210
2 Bedroom | 2 Bath | Sleeps 6

Sunrise Suites - Bonaire Suite 210 - Key West, FL

$336 avg / night

View 160 more homes

Recent Key West vacation rental reviews

This is the second time we have stayed in the Old Town Gardens Villas. It is a great location right in the center of Old Town. The courtyard is amazing. The Andros Suite was cute, clean and very comfortable. I highly recommend staying here. I know I will again!
Kristin B. | Oct 2022
We love the area and the size of the condo. The beds are comfortable and there’s plenty of towels. The price was much better than a hotel room.
Patricia G. | Oct 2022
Great place to stay. Close to Duvall and Higgs beach. Will stay again.
Justin A. | Sep 2022
Key West Frequently Asked Questions

Yes, 85 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. 172 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

Where is Key West, FL?

Our Key West vacation rentals, condos, and cottages are on the last island of the Florida Keys chain, about 160 miles from Miami and 98 miles from Key Largo. Whether you chose to arrive at this interesting island via plane, ferry, or car, the first sight of the expansive Atlantic Ocean promises to take your breath away. With its vibrant wildlife, you may even be lucky enough to spot a few dolphins splashing around and welcoming you to Key West.

Things to do in Key West, FL

When you book one of our Key West, Florida beach house rentals, you're not just booking a vacation—you're booking an experience! Although the island is relatively small, the number of attractions is vast and varied. Key West has a diverse arts and history culture, including plenty of galleries, delicious restaurants, and landmarks that are as unique as the Keys themselves. The Hemingway Home, located in Old Key West, is a historical treat for guests who enjoy literature (and six-toed cats). With look-out towers and detailed exhibits of the wrecking business, the Shipwreck Museum is definitely worth a visit.

Other points of interest on the island include the Southernmost Point, and Wyland's Whaling Wall, a gorgeous mural of some of Key West's local aquatic residents. Key West has a laid-back attitude, but its nightlife isn't lacking! Let loose on Duval Street, starting in Mallory Square with its famous Sunset Celebration and working your way down the main drag to the (in)famous Sloppy Joe's. 

Feeling hungry after a long day full of excitement and adventure? Our Key West lodging is conveniently close to many dining options, including restaurants like Help Yourself, an organic cafe and juice bar, and Square One, a fine-dining establishment. 

Outdoor activities in Key West, FL

With so many diverse outdoor activities near our Key West condos and cottage rentals, it might be difficult to decide where to start. However, one thing is for sure–water is Key West's playground. Book a charter with Sunset Sail Key West and admire the wildlife or catch one of those famous Florida sunsets. With early morning sunrise cruises, starlit float trips, snorkeling, and themes like "Cruise Concert" and "Wine and Wind" at dusk, there's something for everyone.

While sandy beaches are not as common in the Keys due to the reef barrier, there are a few favorites that are worth a visit, including Smathers Beach, Ft. Zachary Taylor State Park, and the Dry Tortugas National Park, home to epic sandy beaches and historic Fort Jefferson. 

The natural beauty of Key West has been preserved thanks to the recent emphasis placed on ecotourism. With options for kayaking, scuba diving, or snorkeling, you'll be able to admire wildlife in its natural habitat while helping conservation efforts to maintain the Keys. View the reef up close with a trip on a glass-bottom boat, or try a dolphin-viewing charter.

A beach vacation destination that combines the modern conveniences and comforts of home with a growing environmental awareness (and a memorable nightlife scene), this beautiful island offers a glimpse into all that Florida has to offer. Plan a visit to one of our Key West beach house rentals for a memorable trip full of relaxation, exploration, and unforgettable experiences. 

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