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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 8.7
Fabulous - What previous guests thought, 702 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,403 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 324 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, 862 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 762 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, 1,047 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

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 7.4
Good - What previous guests thought, 1,735 reviews

Holiday Rentals with swimming pools in Key West and nearby

Scored out of 10, guest rating 7.4
Good - What previous guests thought, 16 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$1,547.72 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$1,144.46 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$1,132.82 per night
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 187 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$308.19 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 6 reviews

Set in the centre of Key West, 300 metres from South Beach and 400 metres from Southernmost Point, Keys Please! offers free WiFi, a garden and air conditioning.

From US$1,615.22 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$246.38 per night
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 15 reviews

In the centre of Key West, located within a short distance of Simonton Street Beach and Duval Street, Sky Loft in Key West offers free WiFi, air conditioning and household amenities such as a...

From US$653.91 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$547.48 per night

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

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$750.94 per night

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.

From US$581.40 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$1,044.10 per night

Curry House - Room 2

Downtown Key West, Key West
Free cancellation options available

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$522.79 per night

Curry House - Room 1

Downtown Key West, Key West
Free cancellation options available
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$537.02 per night

Sunnyside Up

Downtown Key West, Key West
Free cancellation options available
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$893.53 per night
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 261 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$223.88 per night

Rose Lane Villas

Downtown Key West, Key West
Free cancellation options available
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 298 reviews

Located in Key West, Florida, these villas feature a heated outdoor swimming pool. They are adjacent to dining and shopping on Duval Street. and 1.8 km from the Southernmost Point.

From US$415.13 per night

Enjoy breakfast in Key West and nearby

Scored out of 10, guest rating 7.4
Good - What previous guests thought, 1,735 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$175.60 per night
Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 469 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$417.64 per night

Paradise Suite has a patio and is situated in Key West, within just 400 metres of Duval Street and 300 metres of Ernest Hemingway Home and Museum.

Scored out of 10, guest rating 7.8
Good - What previous guests thought, 28 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.

Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 13 reviews

Situated in the centre of Key West, 700 metres from South Beach and 200 metres from Ernest Hemingway Home and Museum, Just steps to Duval- Sleeps 10- Heated Pool House offers free WiFi, a garden and...

Set in the centre of Key West, 700 metres from South Beach and 200 metres from Ernest Hemingway Home and Museum, BachelorPARTY HQ for 16-Feet to Duval-Pool-Hot tub offers free WiFi, a garden and air...

Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 17 reviews

Located in the centre of Key West, 700 metres from South Beach and 400 metres from Duval Street, Road's End offers free WiFi, a garden and air conditioning.

From US$622.86 per night
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 153 reviews

Located right off Duval Street, the Andrews Inn and Garden Cottages are less than 5 minutes’ walk from various dining and entertainment options. Guests can enjoy free WiFi and an outdoor pool.

Highly rated holiday rentals in Key West and nearby

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 12 reviews

Right in the heart of Key West, situated within a short distance of Simonton Street Beach and Key West Aquarium, Mesa House, Dos -Unreal Location offers free WiFi, air conditioning and household...

From US$1,004.91 per night
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 9 reviews

Attractively situated in Key West, Classic King Balcony at the James House features air-conditioned rooms, a garden and free WiFi.

Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 43 reviews

Ideally set in the centre of Key West, King Suite at Curry Mansion with Heated Pool! features free WiFi throughout the property and a garden.

Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 702 reviews

Within walking distance of the beach, local attractions and activities, this Old Town Key West inn features on-site laundry facilities, comfortable guest rooms and an extended continental breakfast.

From US$363.83 per night
Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 48 reviews

Set in Key West, 6.5 km from Southernmost Point and 7.3 km from Ernest Hemingway Home and Museum, The Barbados -Bright Condo w Pool offers air conditioning.

From US$651.60 per night
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 9 reviews

Featuring air-conditioned accommodation with a balcony, Crawl to Duval w/ Hot tub is located in Key West. This property offers access to a terrace and free private parking.

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 5 reviews

In a central area of Key West, located within a short distance of South Beach and Duval Street, Poolside Suite offers free WiFi, air conditioning and household amenities such as an oven and kettle.

From US$748.63 per night
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 16 reviews

Seagrass Suite features a terrace and is located in Key West, within just 200 metres of Ernest Hemingway Home and Museum and 600 metres of Duval Street.

FAQ about holiday rentals in Key West

Holiday rentals that guests love in Key West

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Avg. price/night: US$415.13
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 298 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
Avg. price/night: US$246.38
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 333 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
Avg. price/night: US$246.38
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 333 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$415.13
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 298 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