Discover a selection of 400 vacation rentals in Key West, FL that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $113 per night, and houses and cottages are popular options for a stay in Key West. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Key West
Destination guide

Explore scenic beauty from a Key West villa rental

The unique island city of Key West is one of the best vacation spots for Florida villa rentals. You can experience mile after mile of emerald waters and coral reefs as you drive the Overseas Highway along the Florida Keys archipelago to the farthest southern point that is Key West. You've never had a vacation getaway quite like Key West. This historic former pirate haven is one of the best spots for snorkeling and diving anywhere in Florida. If you love shrimp or crabs, you are in for a delicious treat thanks to the fresh seafood restaurants in Key West.

Things to do

Admire local talent at Studios of Key West

Free-spirited Key West has long been a haven for artists and creatives. There's no better place to discover the scene than The Studios of Key West, a 3-story space showcasing works from local artists. Continue the theme at Hemingway House, a handsome Spanish Colonial estate that was once a sanctuary for the American novelist. If you want to meet one of Key West's most passionate eco-activists, head to Nancy Forrester's Secret Garden. From chirpy parrots to multicolored macaws, this backyard oasis offers a unique opportunity to get up close and personal with exotic Floridian birds.


Splash-happy in Key West

As the sun starts to set, Mallory Square gears up for a night of family-friendly fun. It's essentially one big street party, with fire breathers, tightrope walking dogs, tumbling acrobats and more. You'll also find plenty of action on Duval Street, a lively strip lined with neon-lit bars, theaters, galleries and boutiques. For a quieter scene, why not retreat to the deck of your Key West vacation rental villa for fruity Rum Runner cocktails and Floridian sunsets? For more action, you can snorkel at coral reefs, kayak in crystal-clear water, swim with dolphins, sail on catamarans and more.


Catch Key West's Fantasy Fest celebrations

Craving a dose of winter sunshine? Escape to Key West vacation rentals and you'll find yourself immersed in a tightknit community of locals. Chances are you'll soon be sharing key lime pie with your new neighbors. Locals cite spring as a Key West sweet spot. Crowds taper off and temperatures continue to hover around the 80s. Visit in the last week of October and you'll catch Key West's raucous Fantasy Fest celebrations. The 10-day street party sees the island come alive with pet parades, burlesque shows, costumed events, street food stalls and more.

Natural features

Pet-friendly vacations in Key West

With a footprint measuring in at just 7 square miles, Key West feels wonderfully intimate. It's part of the Florida Keys archipelago and sits just 90 miles from Cuba. You can find out more about the low-lying archipelago at the Florida Keys Eco-Discovery Center, a family-friendly learning space filled with interactive displays and rainbow-colored sea creatures. traveling with Fido? No problem. Floridians love their furry friends, which means you'll find plenty of pet-friendly Key West vacation rentals.

How to get there

Transportation to and around Key West

Fly into Key West Intl. Airport (EYW), the closest airport, located 3 mi (4.8 km) from the city center.

What are the top vacation rentals in or near Key West?

Whatever vacation experience you're seeking, you'll find a rental in or around Key West that's a perfect match. These are some of our top picks:

  • "Sombrero Beach Home On Canal With Private Dock And Heated Pool" is popular with guests. Around 45 miles from Key West, it has 3 bedrooms and lots of amenities to help you feel at home, including a living room and cookware, dishware and utensils.
  • Another great option is "Key West Oasis, Seperate Cottage", which is around 1 mile from Key West. With 2 bedrooms, towels and air conditioning, it has everything you need to make your stay comfortable.

For even more great options, use the search bar at the top of the page to find the perfect Key West vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Key West?

If you've been busier than a squirrel in a nut factory, you deserve to escape for a few days. Skip out of work early on Friday and live it up at one of these weekend getaways in or near Key West:

  • Find some peace at "Casa Cove Beautiful Tropical Decorated 3 King Suites Pool 2 Mi Beach". Located about 4 miles to the east of Key West, this delightful escape has all you need for a chilled out stay, including heating and coffee and tea making facilities.
  • "Starfish - Sunny Townhome In Quiet Truman Annex Two Blocks From Duval St" is another fantastic option to consider. It's located about 0.1 miles to the southwest of Key West and features coffee and tea making facilities, nearby birdwatching activities and more.

Can I find studio apartments for rent in and around Key West?

Studio apartments may be small in size, but they pack a punch when it comes to location and convenience. Plonk your bags down at one of these top studio apartments in or near Key West:

  • After a fun-filled day of urban exploration, come home to the comforts of "Condo In Old Town Key West's Truman Annex". A hair dryer and high-speed internet services are among the handy amenities on offer here.
  • An equally fantastic property is "Your Condo By The Beach With Ocean View". Don't let its modest size fool you — this cozy apartment is filled with handy amenities like a nearby laundromat, an elevator and lots more.

Can I find short term rentals in or near Key West?

From funky studio apartments to extravagant houses, Vrbo has your quick escape sorted. Here are just two of our favorite stays in and around Key West:

  • Close to the center of Key West, "Coconut Sunsets And Open Water Views" welcomes short-term guests. When you're not chilling out in your comfortable digs, get out and discover all the fun stuff around you.
  • "Cloud 9 ~ It's Heaven On Earth In This 3b" is also well located. Settle in here and find out why lots of guests rate this property as one of their favorites.

What are the best romantic weekend getaways in or near Key West?

Nothing says "I love you" like a romantic weekend together. If you'd like to spend a couple of relaxing nights away with your sweetie, we've got some romantic getaways in and around Key West that will sweep you off your feet:

  • Sneak off on Friday for a couple of passion-filled evenings at "Key West Oasis, Seperate Cottage". Roughly 1 mile from Key West, this property comes with lots of nice touches, including beauty services and outdoor furniture.
  • "Cloud 9 ~ It's Heaven On Earth In This 3b" is another wonderful option guaranteed to woo you. It's about 0.1 miles from Key West and comes with a nearby marina and a swimming pool.

Are there mansions for rent in or near Key West?

We've got some awesome mansions for rent in and around Key West. If you're chasing somewhere with plenty of room as well as a large dose of wow factor, these stunners will tick your boxes:

  • Around 0.1 miles to the southwest of Key West is "Noona's Mansion @ The Annex Grand Home And Pool + Last Key Services". Along with its grand design, you'll be impressed by its first-class amenities, such as a swimming pool and beauty services.
  • With a swimming pool, golf and a host of other top-notch amenities, "Captiva" ~ , Historic Mansion Suite With Community Pool" will get your guests' nod of approval. This opulent home is around 1 mile to the east of Key West.

What are the best large group vacation rentals in or near Key West?

Big groups mean enormous fun. They also mean finding a place that'll comfortably fit your crew. Check out our large group vacation rentals in or around Key West and get your favorite people together under the same roof:

  • Providing space, privacy and comfort, you'll get everyone's seal of approval at "New Photos: Drive To Your Getaway". Up to 12 people can be accommodated at this property which has 5 bedrooms, a swimming pool and a beach view. This group getaway is around 1 mile to the southeast of Key West.
  • Invite as many as 14 of your favorite people to "William Skelton Home - Heart Of Key West" and fill the place with love and laughter. This top option has 6 bedrooms and is around 0.1 miles to the north of central Key West. It's packed with features to keep a large group comfortable, including a swimming pool and a garden.

Are there large vacation rentals that sleep 30 or more in or near Key West?

Now and then you just have to escape from it all ... With, oh, 30 or more of your loved ones. Whether you're looking for someplace to stay with the extended fam or you're organizing a shindig, we have large vacation rentals in and around Key West that'll fit your whole party:

  • "All Together Now @ Old Town Three Homes And Pools + Last Key Services": With 13 bedrooms accommodating up to 32 people, there's enough space for everyone. You and your guests will have access to amenities including a swimming pool and a balcony.
  • "Six Dog - Friendly Homes In Quiet Neighborhood With Private Pool And Hot Tub": This sought-after getaway was made for big groups and features a swimming pool and a kitchen. It contains 12 bedrooms and caters for up to 34 people.

What are the best houses for rent with a pool in or near Key West?

A pool is often an all-important amenity when choosing where to stay on vacation, particularly if you're taking the kids. Check out these houses with a pool in or near Key West and fill your days with frolicking good fun:

  • Pack your swimming gear and take your gang to "Casa Capri Beautiful Tropical Style House With 3 King Suites Pool 2 Mi To Beach". There are plenty of other convenient amenities here, including a porch and a fenced pool.
  • Spend leisurely vacation days splashing around or simply unwinding by the water at "Casa Cay West Beautiful Tropical House 3 Bedrooms 2 King Suites Pool 2 Mi Beach". This vacation home is also a firm favorite and features a porch, a swimming pool and more.

Key West has a tropical savanna climate, with average summertime temperatures ranging from 80 ºF to 85 ºF. But there's no need to wait until summertime to visit. Check out the search bar at the top of the page and adjust the filters to find the perfect Key West vacation rental and organize your getaway for whatever season you like.

What are the best large family vacation rentals in or near Key West?

Every family get-together should be memorable. Whether you're organizing a fun escape with the kids or that long-overdue family reunion, our large family vacation rentals in or near Key West offer a home away from home with enough space for everyone:

  • Sleeping as many as 7 guests in 3 bedrooms, "Cloud 9 ~ It's Heaven On Earth In This 3b" is the perfect place for some family time. This popular retreat is 0.1 miles to the north of Key West and has amenities that include a swimming pool and a fridge.
  • Another popular option is "Casa Cove Beautiful Tropical Decorated 3 King Suites Pool 2 Mi Beach". This vacation rental is 4 miles east of Key West and features a stereo, childrens activities and more. With 3 bedrooms accommodating up to 8 people, there's no need to leave anyone off your invitation list.

If you're hoping to visit some family-friendly attractions around the area, you're spoiled for choice. Dolphin Research Center, The Turtle Hospital and Great White Heron National Wildlife Refuge promise lots of fun for all ages.

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