Key West Vacation Rentals

Compare 181 vacation rentals. Enter your trip dates to get started.
USA > Florida > Key West

Make Key West your next getaway—choose from 181 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


Condo rentals

View 82 Condo rentals

House rentals

View 42 House rentals


View 29 Studios

Key West vacation rentals for every getaway

Dog-friendly Hot tub Internet
Casa Caribe @ Duval Square R9 3D Tour
2 Bedroom | 2.5 Bath | Sleeps 6

Casa Caribe @ Duval Square R9 - Key West, FL

From $190
Atlantic Parrot
2 Bedroom | 2 Bath | Sleeps 6

Atlantic Parrot - Key West, FL

From $237
Truman @ Duval - Two Bedroom 3D Tour
2 Bedroom | 1 Bath | Sleeps 4

Truman @ Duval - Two Bedroom - Key West, FL

From $166
Sunrise Suites - Paradise Escape 407 3D Tour
2 Bedroom | 2 Bath | Sleeps 6

Sunrise Suites - Paradise Escape 407 - Key West, FL

From $186
Sunrise Suites - Sea Breeze Suite 101 3D Tour
2 Bedroom | 2 Bath | Sleeps 6

Sunrise Suites - Sea Breeze Suite 101 - Key West, FL

From $165

View 176 more homes

Recent Key West vacation rental reviews

Full kitchen, washer/dryer, decent bed, & hot tub. Pool is very shaded and didn’t seem heated. Good location. TV’s need upgraded would be my only suggestion.
Colin S. | Oct 2021
Perfect spot for 3 couples. A unicorn with 3 king beds. Nice cold A/C and warm hot tub on private patio. We rented a golf cart which was the perfect way to get around.
LYNNE M. | Oct 2021
We loved our accommodations at the Sunrise Suites! Very clean and lots of space! I found it very convenient that they would text me reminders and the door code that helped simplify our travel plans. The only difficult part we had was the late check in (after 4pm) and the early (10 am) check out. We traveled to Key West by the ferry and arrived around noon. It would have been nice to check in earlier so we could change and stop off our bags. But overall a great experience and would use them again!
Alise R. | Oct 2021

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. 

Key West travel inspiration

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

Unique Weekend Getaways in Florida