Key West Vacation Rentals

Compare 186 vacation rentals. Enter your trip dates to get started.
USA > Florida > Key West

Make Key West your next getaway—choose from 186 great Key West 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 84 Condo rentals
housing_type_house.jpg

House rentals

View 48 House rentals
housing_type_studio.jpg

Studios

View 30 Studios

Key West vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Papa's Hideaway  - Garden of Eden 3D Tour
2 Bed | 2 Bath | Sleeps 6

Papa's Hideaway - Garden of Eden - Key West, FL

From $359
Bright Key West Beauty 3D Tour
2 Bed | 2.5 Bath | Sleeps 5

Bright Key West Beauty - Key West, FL

From $180
Rhum Rampant 3D Tour
3 Bed | 2 Bath | Sleeps 8

Rhum Rampant - Key West, FL

From $151
Commodore's Cove 3D Tour
4 Bed | 4 Bath | Sleeps 12

Commodore's Cove - Key West, FL

From $499
Casa Bonita @ Duval Square R1 3D Tour
2 Bed | 2.5 Bath | Sleeps 6

Casa Bonita @ Duval Square R1 - Key West, FL

From $280

View 181 more homes

Recent Key West vacation rental reviews

Awesome house. Had a group of 6 YA there. The back pool area is perfect with the pool set up plus outdoor dining. We spent the majority of our time out there as we also had great weather. House was about a 15 min walk to Duval so also perfect there. Only downside is the pull out couch was not the best comfort so we slept on couches instead. There are a few corner stores in the area to buy beverages but would highly recommend going to a grocery for food as we had an issue with some OOD food from the corner stores. Overall we loved this house and would definitely rent again!
Trisha R. | Nov 2020
Location and cleanliness could not be bit! Already planning our return to this unit! Vacasa was a pleasure to work with! Very responsive!!!
Lori F. | Nov 2020
Perfect home with beautiful view !
Laetitia W. | Nov 2020

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