Key West Vacation Rentals

Compare 179 vacation rentals. Enter your trip dates to get started.
USA > Florida > Key West

Make Key West your next getaway—choose from 179 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

housing_type_condo.jpg

Condo rentals

View 78 Condo rentals
housing_type_house.jpg

House rentals

View 45 House rentals
housing_type_studio.jpg

Studios

View 29 Studios

Key West vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Sunrise Suites - Saint Thomas Suite 302 3D Tour
2 Bed | 2 Bath | Sleeps 6

Sunrise Suites - Saint Thomas Suite 302 - Key West, FL

From $177
Sunrise Suites - Panama Suite 310 3D Tour
2 Bed | 2 Bath | Sleeps 6

Sunrise Suites - Panama Suite 310 - Key West, FL

From $153
Sunrise Suites - Dominican Suite 110 3D Tour
2 Bed | 2 Bath | Sleeps 6

Sunrise Suites - Dominican Suite 110 - Key West, FL

From $199
Sunrise Suites - Antigua Suite 312 3D Tour
2 Bed | 2 Bath | Sleeps 6

Sunrise Suites - Antigua Suite 312 - Key West, FL

From $168
Sunrise Suites - Cozumel Suite 112 3D Tour
2 Bed | 2 Bath | Sleeps 6

Sunrise Suites - Cozumel Suite 112 - Key West, FL

From $179

View 174 more homes

Recent Key West vacation rental reviews

Great location and loved the space. The bathrooms were a little outdated but everything worked great and was clean. Overall great stay.
Jessica A. | None
We absolutely loved this place. The location was perfect for us. Very nice, and not too much traffic noise. The fire detector went off one night at 4 in the morning, but we disconnected it and all was good again. It was a very old detector, so probably just defective. The kitchen was perfect for us, and the outdoors was beautiful. Very tropical. The pool was too warm for us to get in though. The bed was firm and we loved that! Definitely a keeper in our books!
Raleigh T. | None
This is an adorable home within walking distance of the main attractions like the Southernmost points and Duval Street and just a few short driving miles from grocery stores and the airport. The landscaping and pool area are well-kept. We enjoyed having in home amenities like pool/bath towels, dishes for cooking and eating, basic toiletries, cable TV, and WiFi. The home is a bit worn but it is to be expected with the weathering homes receive in that area and the continual turnaround of guests during high occupancy months. We had two minor issues that were fixed within just a few hours of reporting them. We also appreciated that the Vacasa staff checked in often to ensure our stay was going well. If you are visiting Key West with family/friends and looking for a relaxing place within walking distance to some great places and a pool to cool off in, this is the place!
KRISTINE H. | None

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 are 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. 

Discover Key West

4 Florida Keys Races and Marathons for Every Skill Level

The Ultimate Escape: Key West Cottages with Private Pools

Plan Your Florida Keys Snorkeling Vacation

Creative Getaways: An Artist Retreat for Every Medium