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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

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L'Habitation Guesthouse- Adult Exclusive

Downtown Key West, Key West

Located in Key West, 600 metres from Key West Aquarium and 600 metres from Mallory Dock, L'Habitation Guesthouse- Adult Exclusive provides accommodation with free WiFi, air conditioning, a garden and...

J
Jannik
From
Germany
Very nice guesthouse in perfekt shape in the best location. The owner is very nice na happy to help whenever needed.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,412 reviews
Price from
US$219
1 night, 2 adults

Southernmost Point Guest House & Garden Bar

Downtown Key West, Key West

This Key West, Florida Southernmost Point Guest House & Garden Bar is located on Duval Street 110 metres from the Southernmost Point and 73 metres from the beach.

S
Silje Helene
From
Norway
Was not expecting much when I booked but I can't praise this place enough! The atmosphere, the rooms, the design, the location, the staff. It was just perfect from start to finish! Will be back!
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,176 reviews
Price from
US$481.85
1 night, 2 adults

Old Town Manor

Downtown Key West, Key West

This adult-only, pet friendly, smoke-free property is located in the heart of Key West less than 1.6 km from the Southernmost Point.

N
Nicola
From
United Kingdom
The breakfast had lots of choices and quality ingredients, the location was on a street with lots of old character property and adjacent to Duval street with shops, bars and restaurants
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,046 reviews
Price from
US$289
1 night, 2 adults

The Casablanca Hotel

Downtown Key West, Key West

Less than 2 minutes’ walk from the Ernest Hemingway Home and Museum, this historic Key West property features guest rooms with private balconies and free Wi-Fi.

S
Steve
From
Canada
The staff was very friendly and the room was very clean. The location was great as well. The bedding felt luxurious, and was a comfy sleep.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 519 reviews
Price from
US$135
1 night, 2 adults

Key West Villas

Downtown Key West, Key West

Located in the heart of historic Key West, guests will be 1 minutes’ walk from Duval Street. A heated pool, daily continental breakfast, and free WiFi are provided.

P
Peter McGuigan
From
Australia
Exceptional facilities. It seemed to me that they had thought of every possible need. We loved the happy hour cocktails and mixing with the other guests. Plenty of choice for breakfast. Located in a very central part of the main town. Heather and Kevin were friendly and generous. A great stay.
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 340 reviews
Price from
US$979
1 night, 2 adults

The Artist House

Downtown Key West, Key West

This historical Key West bed and breakfast is 1 mile from the Southernmost Point and 3 minute’s walk from iconic Duval Street.

K
Kaicheng
From
United States
Great breakfast, beautiful room decor, perfect location
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 194 reviews
Price from
US$219.45
1 night, 2 adults

Evershore House -Pool, Parking, Dock!

Key West

Featuring air-conditioned accommodation with a private pool, Evershore House -Pool, Parking, Dock! is located in Key West.

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 5 reviews
Price from
US$1,537.55
1 night, 2 adults

Sky Loft in Key West

Downtown Key West, Key West

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...

P
Patrick
From
United Kingdom
Location, and general layout of the property.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 15 reviews
Price from
US$372.60
1 night, 2 adults

The Island Suite at KW Vacation

Downtown Key West, Key West

In a central area of Key West, set within a short distance of Simonton Street Beach and Duval Street, The Island Suite at KW Vacation offers free WiFi, air conditioning and household amenities such as...

S
Siobhan
From
United Kingdom
Lovely suite in a very nice complex beautiful peaceful surroundings.
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 38 reviews
Price from
US$369
1 night, 2 adults

The Bartlum-Luxurious Studio

Downtown Key West, Key West

In a central area of Key West, located within a short distance of Simonton Street Beach and Key West Aquarium, The Bartlum-Luxurious Studio offers free WiFi, air conditioning and household amenities...

S
SIqintana
From
United States
Offering free parasol/shade umbrella service is great.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 46 reviews
Price from
US$244.26
1 night, 2 adults
All 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, 715 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, 519 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 772 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 318 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,412 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,176 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 7.4
Good - What previous guests thought, 1,759 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,048 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 659 reviews

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

Road's End

Downtown Key West, Key West
Free cancellation options available
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$1,326.66 per night
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$2,439.11 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$1,696.89 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!

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 26 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$1,264.56 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.

From US$925.54 per night

Keys Please!

Downtown Key West, Key West
Free cancellation options available
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 7 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$2,260.80 per night

Highly rated holiday rentals in Key West and nearby

Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 472 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$371.36 per night
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 25 reviews

Boasting air-conditioned accommodation with a patio, Amelia House is situated in Key West.

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 813 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$257.63 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 190 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$272.63 per night
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 29 reviews

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

From US$402.30 per night
Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 14 reviews

Key Lime Calypso is set in the Downtown Key West district of Key West, 200 metres from Ernest Hemingway Home and Museum, 200 metres from Duval Street and less than 1 km from Southernmost Point.

Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 1,280 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, 398 reviews

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

From US$363.04 per night

Holiday Rentals with swimming pools in Key West and nearby

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 659 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$257.63 per night
Scored out of 10, guest rating 7.7
Good - What previous guests thought, 122 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, 862 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$403.88 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$687.21 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$635.34 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$662.51 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$1,643.91 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$246.38 per night

Enjoy breakfast in Key West and nearby

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 859 reviews

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

From US$392.34 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 318 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$201.38 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 345 reviews

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

Scored out of 10, guest rating 7.4
Good - What previous guests thought, 1,759 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$226.23 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 1,145 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

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 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.

Scored out of 10, guest rating 8.2
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...

FAQ about holiday rentals in Key West

Holiday rentals that guests love in Key West

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Avg. price/night: US$358.88
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 300 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$392.63
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 340 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$392.63
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 340 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$358.88
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 300 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