Key West Vacation Rentals

Compare 150 vacation rentals. Enter your trip dates to get started.
USA > Florida > Key West

Make Key West your next getaway—choose from 150 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 79 Condo rentals
housing_type_house.jpg

House rentals

View 37 House rentals
housing_type_studio.jpg

Studios

View 15 Studios

Key West vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Sunrise Suites - Bonaire Suite 210 3D Tour
2 Bedroom | 2 Bath | Sleeps 6

Sunrise Suites - Bonaire Suite 210 - Key West, FL

From $211
Ibis Suite 3D Tour
0 Bedroom | 1 Bath | Sleeps 4

Ibis Suite - Key West, FL

From $278
Sunrise Suites - Dominican Suite 110 3D Tour
2 Bedroom | 2 Bath | Sleeps 6

Sunrise Suites - Dominican Suite 110 - Key West, FL

From $223
Palm Isle 3D Tour
1 Bedroom | 1 Bath | Sleeps 4

Palm Isle - Key West, FL

From $327
Papa's Hideaway #3 - For Whom the Bell Tolls 3D Tour
0 Bedroom | 1 Bath | Sleeps 4

Papa's Hideaway #3 - For Whom the Bell Tolls - Key West, FL

From $346

View 145 more homes

Recent Key West vacation rental reviews

My mom and I stayed here for 4 nights and thought it was a great place. It has nice clean sheets on the beds, lots of different towels, lots of eco-labeled products (such as soap, shampoo, conditioner), coffee machine, iron, hair dryer, microwave, stove, fridge, etc. Perfect for those who want to stay a bit longer and consider making food instead of going out for every meal. We were unable to find the remote for the tv, so we did not end up watching tv at all. We had our phones though, so that wasn't really an issue. Worth noting is also that the walls are very thin, so noise from neighbors (yelling, loud tv, showers, flushing, etc.) and any parties going on might bother you. The biggest issue we had was that the floors did not seem to be cleaned, or at least maybe not well enough. We're European so we don't use shoes indoors and our feet got very dirty from just walking around inside. There were also some hairs on the floor in the bathroom (further indicating that the floors had not been cleaned). Other than that, it was a perfect location within walking distance to everything. We enjoyed our stay. We would definitely book this location again!
Kellie S. | Dec 2021
As a 15 year ski in/out VRBO rental owner We've worked hard to make our place a great vacation venue for amazing family vacations. This perspective allows us to honestly review the property. Let me start by saying ALL in our group were more than happy with their accommodations during our family reunion. The pool was a hit with our young ones. They swam late each evening allowing others to talk while watching them wear themselves out. If you are looking for a new constructed place this may not be for you. That said everything was completely functional, worked great and the age added a little Key West charm. Located a few blocks off of Duval st allowed everyone to come and go at their leisure. If you have a large group visiting Key West you should really consider a stay here. One last comment regarding local Vacasa staff. They went above and beyond to make our group feel valued and assure we had a good stay. Quick responsive communication with follow up. Plenty of bath soaps, shampoos, dish soap, towels, beach towels............... This type of service is hard to come by and separates great venues from just a place to stay.
jeff s. | Dec 2021
Family of 5 with teens and adults, but no married kids. The 2nd BR would be fine for another couple. Top floor. If you plan to cook bring your spices and condiments as they don't stock. Grounds are fabulous. 4-5 tennis courts. Pool and hot tub area is superb! Hot tub was very warm when we were there which was perfect.
Greg H. | Dec 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