Key West Vacation Rentals

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Make Key West your next getaway—choose from 156 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 79 Condo rentals
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House rentals

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Studios

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Key West vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Passover Cottage 3D Tour
2 Bedroom | 2 Bath | Sleeps 4

Passover Cottage - Key West, FL

From $430
Ibis Suite 3D Tour
0 Bedroom | 1 Bath | Sleeps 4

Ibis Suite - Key West, FL

From $132
Old Town Garden Villas - Andros Suite 3D Tour
1 Bedroom | 1.5 Bath | Sleeps 4

Old Town Garden Villas - Andros Suite - Key West, FL

From $173
Hemingway's View 3D Tour
3 Bedroom | 2 Bath | Sleeps 8

Hemingway's View - Key West, FL

From $472
Tropical Village - Poolside Paradise 3D Tour
0 Bedroom | 1 Bath | Sleeps 2

Tropical Village - Poolside Paradise - Key West, FL

From $146

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Recent Key West vacation rental reviews

2nd Vacasa we have stayed in. Another great property. Much better value than staying in a hotel. Would stay again and highly recommend.
Jeffrey P. | May 2022
This little place was a great location. Walking distance to the popular sites. a great little cuban place on the corner. I loved that the cottage was not on the main street, but hidden behind some other buildings. The cottage was clean and comfortable. We could hear a little noise, but it was never a big deal and we still slept great. Would highly recommend.
Toni S. | May 2022
Wonderful little efficiency apartment. Very clean and nice pool. We also had a ga grill for ur use. Private patio, which was nice for early morning coffee. Close to Duval. We will definitely be back. Someone local checked to see if we were enjoying our stay and asked if we needed anything. Very nice to have the customer service.
Shelly M. | May 2022

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. 

Key West travel inspiration

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