Discover a selection of 40 holiday rentals in Key West, FL, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including pool and private pool. Prices start at £ 148 per night, and houses and flats & apartments 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

Take in the picturesque beauty of Key West

The area's live music and festivals are just some of the reasons to come on holiday to Key West. This city's bars, seaside and boating draw many visitors. Take in top local attractions such as Duval Street and Mallory Square. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Things to do

Activities and attractions in Key West

Are you hoping to find attractions to see while you're in town? Travellers enjoy fun activities like boating and cycling. Venture out of your cosy holiday rental and experience everything that makes Key West a one-of-a-kind holiday spot. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Key West Golf Club (4 mi / 6.5 km)
  • The Kite House (0.3 mi / 0.5 km)
  • MLK Community Pool & Community Center (0.5 mi / 0.8 km)
  • Blue Hole (28.6 mi / 46.1 km)
  • Key West Visitors Center (29.9 mi / 48.2 km)
Natural features

Exploring the natural landscape of Key West

Travellers love Key West for its breathtaking sunsets and beautiful ocean views. Whether you're looking for adventure or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Key West. These are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Smathers Beach (1.7 mi / 2.8 km)
  • Audubon House and Tropical Gardens (0.3 mi / 0.6 km)
  • Key West Butterfly and Nature Conservatory (0.6 mi / 0.9 km)
  • Fort Zachary Taylor Historic State Park (0.6 mi / 1 km)
  • Southernmost Point (0.6 mi / 1 km)
  • South Beach (0.7 mi / 1.1 km)
How to get there

Transport to and around Key West

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

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

Whatever holiday 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 holiday rental for you.

What are the top-rated holiday 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 cosy 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 favourite stays in and around Key West:

  • Close to the centre 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 favourites.

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's the best place to stay if you're looking to rent a house for a weekend in or near Key West?

Roughly 1 mile from Key West, Old Town Key West is the ideal place to escape to if you don't have much time but want an adventure. Spend your days exploring this well-known commercial suburb and your evenings relaxing at one of our superb holiday homes. Or, check out our range of rental houses in the urban suburb of Key West Historic District, which is about 0.1 miles from Key West.

What are the best large group holiday 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 holiday rentals in or around Key West and get your favourite 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 favourite 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 holiday 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 organising a shindig, we have large holiday 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 Neighbourhood 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 holiday, 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 holiday 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 holiday home is also a firm favourite and features a porch, a swimming pool and more.

Key West has a tropical savanna climate, with average summertime temperatures ranging from 80null to 85null. 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 holiday rental and organise your getaway for whatever season you like.

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