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Holiday Rentals in Key West

Find the holiday rentals that appeal to you the most

The best holiday rentals in Key West

Check out our pick of great holiday rentals in Key West

Most booked holiday rentals in Key West and surroundings in the past month

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Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 707 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,409 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 518 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 321 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 863 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 769 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,168 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,049 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 7.4
Good - What previous guests thought, 1,745 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 653 reviews

Highly rated holiday rentals in Key West and nearby

Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 470 reviews

Located in Key West, Florida, these furnished self-catering apartments feature free WiFi access. The Ernest Hemingway Home and Museum is only 3 minutes’ walk away from Old Town Suites.

From US$338.63 per night
Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 27 reviews

Boasting air-conditioned accommodation with a patio, Hemingway's View is situated in Key West. Located in the Downtown Key West district, the property provides guests with access to a hot tub.

From US$1,273.05 per night
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 17 reviews

Located within the Downtown Key West district in Key West, Road's End has air conditioning, a patio, and city views.

From US$743.18 per night
Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 14 reviews

Located in the centre of Key West, 600 metres from South Beach and 500 metres from Ernest Hemingway Home and Museum, New Casa Caribe by Brightwild- Two-Story Condo Rooftop Pool offers free WiFi and...

From US$1,201.39 per night
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 27 reviews

In the heart of Key West, set within a short distance of South Beach and Ernest Hemingway Home and Museum, Sea Breeze -Great Location!

From US$831.15 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 805 reviews

Located centrally on lively Duval Street, Duval House offers a continental breakfast that includes Belgian waffles. The 7 Caribbean-style buildings offer free WiFi.

From US$235.13 per night
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 189 reviews

Located above a nightclub on historic Duval Street in Key West, Florida, this gay male guest house features an outdoor swimming pool, a clothing-optional sundeck, and an on-site restaurant.

From US$248.92 per night
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 30 reviews

This adult-only Conch House Heritage Inn offers accommodation in Key West with breakfast included and complimentary mimosas.

From US$321.30 per night

These holiday rentals in Key West and nearby have options with free cancellation

Scored out of 10, guest rating 7.4
Good - What previous guests thought, 17 reviews

Right in the heart of Key West, situated within a short distance of South Beach and Ernest Hemingway Home and Museum, Casa Key West-Pool & Free Parking offers free WiFi, air conditioning and household...

From US$1,511.49 per night
Scored out of 10, guest rating 5.0
Passable - What previous guests thought, 2 reviews

Set in the centre of Key West, 600 metres from South Beach and 500 metres from Ernest Hemingway Home and Museum, NEW!

From US$1,290.66 per night

Coconut Palm

Downtown Key West, Key West
Free cancellation options available
Scored out of 10, guest rating 5.5
Passable - What previous guests thought, 2 reviews

Right in the heart of Key West, situated within a short distance of South Beach and Ernest Hemingway Home and Museum, Coconut Palm offers free WiFi, air conditioning and household amenities such as a...

Traveler's Palm

Downtown Key West, Key West
Free cancellation options available
Scored out of 10, guest rating 7.8
Good - What previous guests thought, 45 reviews

Located within the Downtown Key West district in Key West, Traveler's Palm has air conditioning, a patio, and city views.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Located in the centre of Key West, less than 1 km from South Beach and a 3-minute walk from Duval Street, Contra House -Luxury Home With Pool offers free WiFi, a garden and air conditioning.

From US$1,410.58 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 653 reviews

Set in Key West, less than 1 km from South Beach, La Pensione Inn - Adult Exclusive offers accommodation with an outdoor swimming pool, free private parking, a shared lounge and a terrace.

From US$212.63 per night

The Collins on Duval

Downtown Key West, Key West
Free cancellation options available
Scored out of 10, guest rating 6.4
Pleasant - What previous guests thought, 6 reviews

In the heart of Key West, set within a short distance of Simonton Street Beach and Duval Street, The Collins on Duval offers free WiFi, air conditioning and household amenities such as a fridge and...

From US$1,127.94 per night

Duval Dream Loft on Duval

Downtown Key West, Key West
Free cancellation options available
Scored out of 10, guest rating 7.1
Good - What previous guests thought, 26 reviews

Situated in the centre of Key West, less than 1 km from Simonton Street Beach and a 3-minute walk from Duval Street, Duval Dream Loft on Duval offers free WiFi and air conditioning.

From US$1,045.26 per night

Enjoy breakfast in Key West and nearby

Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 1,274 reviews

Offering an outdoor pool, this historic Key West property is just 1 minutes’ walk from Duval Street. Free WiFi and a light continental breakfast are provided daily to all guests.

From US$336.38 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 396 reviews

Featuring free WiFi throughout this adult-only property, Caribbean House offers accommodation in Key West.

From US$363.04 per night
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 71 reviews

Offering a year-round outdoor pool and terrace, this adult-only (21 years +) Marreros Guest Mansion is set in the Duval district in Key West. Duval Street is a 1 minute walk from the property.

From US$365.63 per night
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 862 reviews

This all-adult bed and breakfast is within a 10-minute walk of Duval Street and the Atlantic Ocean.

From US$323.10 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 321 reviews

Key West Bed and Breakfast, a property with a garden, is situated in Key West, 1.2 km from Key West Aquarium, 1.3 km from Ernest Hemingway Home and Museum, as well as 1.1 km from Mallory Dock.

From US$329.65 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 341 reviews

Well located in Key West, The Garden House provides express check-in and check-out and private parking.

From US$235.13 per night
Scored out of 10, guest rating 7.4
Good - What previous guests thought, 1,745 reviews

This bed and breakfast welcomes guests to Old Town, Key West and boasts a free continental breakfast, 3 outdoor pools and a hot tub. The Ernest Hemingway Home and Museum is 15 minutes’ walk away.

From US$216.10 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 1,135 reviews

Featuring free WiFi, a sun terrace with a swimming pool and a garden, Authors Key West Guesthouse is situated in Key West. It is set 1.7 km from South Beach and features a concierge service.

From US$167.63 per night

Holiday Rentals with swimming pools in Key West and nearby

In the heart of Key West, set within a short distance of South Beach and Ernest Hemingway Home and Museum, Southern Palms offers free WiFi, air conditioning and household amenities such as a microwave...

Scored out of 10, guest rating 7.8
Good - What previous guests thought, 124 reviews

Centrally located in Key West's Old Town, this intimate Florida inn offers bright, tropical rooms. It is 4 blocks from the beach and 2 blocks to dining on Duval Street.

From US$291.38 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 863 reviews

Alexander Palms Court - No Hidden Resort Fees! provides accommodation located less than 1 km from the centre of Key West and features an outdoor swimming pool and a garden.

From US$358.88 per night
Scored out of 10, guest rating 7.0
Good - What previous guests thought, 7 reviews

Situated in the centre of Key West, 1 km from Simonton Street Beach and 800 metres from Duval Street, Curry House Room 6 offers free WiFi, a garden and air conditioning.

From US$556.54 per night

Set in the centre of Key West, 1 km from Simonton Street Beach and 800 metres from Duval Street, Curry House - Room 2 offers free WiFi, a garden and air conditioning.

From US$520.20 per night
Scored out of 10, guest rating 6.4
Pleasant - What previous guests thought, 7 reviews

Situated in the centre of Key West, 1 km from Simonton Street Beach, Curry House - Room 1 features air-conditioned rooms and free WiFi.

From US$535.73 per night
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 4 reviews

Located in the centre of Key West, 700 metres from Higgs Beach and 1 km from Southernmost Point, Sunnyside Up offers free WiFi, a garden and air conditioning.

From US$1,088.89 per night
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 260 reviews

Set within 500 metres of Key West Aquarium, Weatherstation Inn Circa 1911 is an adult-only bed and breakfast in Key West and features a number of amenities including an outdoor swimming pool and a...

From US$246.38 per night

FAQ about holiday rentals in Key West

Holiday rentals that guests love in Key West

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Avg. price/night: US$403.88
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 299 reviews
best location!! plenty of space for the family!! i will surely come back and stay the villas!!
Guest review by
Ailen
Family with young children
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 336 reviews
Everything was wonderful. The villas had everything you needed to make your trip enjoyable. Looking forward to going back again soon.
Guest review by
erica
Group
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 336 reviews
Perfect location, but even more importantly, Heather and Kevin were dream hosts. The snacks, cocktails and customer service were outstanding. I would recommend Key West villas to everyone!
Guest review by
Thomas
Group
Avg. price/night: US$403.88
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 299 reviews
Absolutely beautiful great sized villa. Comfortable, convenient location, staff was excellent and villa was spotless. Parking and pet friendly with a nice pool - all excellent bonuses! So nice that when I walked in I immediately called the office and extended my stay by two nights!
Guest review by
lisa
Solo traveller
gogless