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Holiday Rentals in Key West

Find the holiday rentals that appeal to you the most

Top picks for Key West hotels

Explore our most popular hotels 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...

S
Sue
From
Australia
Our host Foster was fantastic. We were welcomed with a smile and made to feel at home. Facilities were good and breakfast was plentiful. The bed was very comfortable. The complex was very close so everything. Just metres away from Duval Street. Thank you for a nice stay. We recommend L' Habitaion Guest house and would loved to have stayed longer.
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 1,383 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.

F
Francesca
From
Switzerland
We had a lovely time in this romantic guesthouse as a 30 y.o. couple. The room was quite big and clean, bathroom was spacious and the balcony was so nice. We were on the first floor, and there was armchairs to sit in outside there and just enjoy the ocean breeze. Magical. The bar was quite cool as well, with live music. A pity that they stop playing at 19:00 and close the bar at 19:30 though. Breakfast was a lot of options, homemade cooking kinda vibe, we enjoyed it a lot. Parking was very convenient, I don’t understand the bad reviews about the distance. Guys, it’s literally 1 minutes walk. It’s good for you, just walk. It’s not gonna kill you. Strongly recommend!
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,172 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.

A
Alice
From
France
Amazing time at the Old Town Manor Cosy room, great breakfast, heartwarming welcome ! Many thanks!
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,041 reviews
Price from
US$289
1 night, 2 adults

Weatherstation Inn Circa 1911

Downtown Key West, Key West

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...

J
JT
From
United Kingdom
Everything. Breakfast were help yourself contintal. Good quality and lots of it. Location really good
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 262 reviews
Price from
US$199
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.

R
Radu
From
Netherlands
Location is perfect. Not on main and noisy street, but close enough to all shops and restaurants. Parking is possible and the private garden with pool is cozy and thoughtful decorated. Host is lovely and breakfast also possible.
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 320 reviews
Price from
US$549
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
Kathryn
From
Australia
Beautiful and historical. Rooms were stunning and so comfortable with all the amenities. The staff were so friendly and helpful and took the time to show me everything and answer any questions I had. Will definitely be back
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 206 reviews
Price from
US$219.45
1 night, 2 adults

Aquaria House -Pool & Boat Dock

Key West

Boasting air-conditioned accommodation with a private pool, Aquaria House -Pool & Boat Dock is situated in Key West.

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 5 reviews
Price from
US$918.85
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$918.85
1 night, 2 adults

Cloud Suite On Duval

Downtown Key West, Key West

Situated in the centre of Key West, less than 1 km from South Beach and a 1-minute walk from Duval Street, Cloud Suite On Duval offers free WiFi and air conditioning.

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 14 reviews
Price from
US$748.65
1 night, 2 adults

Sky Suite On Duval

Downtown Key West, Key West

Set in the centre of Key West, less than 1 km from South Beach and a 1-minute walk from Duval Street, Sky Suite On Duval offers free WiFi and air conditioning.

S
Stavroula
From
Canada
Hosts were SUPER nice and accommodating, location is ideal, and apartment was perfect! Would definitely stay here again.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 10 reviews
Price from
US$906.20
1 night, 2 adults
All holiday rentals in Key West

The best holiday rentals in Key West

Check out our pick of great holiday rentals in Key West

Filter by:

Review score

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...

S
Sue
From
Australia
Our host Foster was fantastic. We were welcomed with a smile and made to feel at home. Facilities were good and breakfast was plentiful. The bed was very comfortable. The complex was very close so everything. Just metres away from Duval Street. Thank you for a nice stay. We recommend L' Habitaion Guest house and would loved to have stayed longer.
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 1,383 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.

F
Francesca
From
Switzerland
We had a lovely time in this romantic guesthouse as a 30 y.o. couple. The room was quite big and clean, bathroom was spacious and the balcony was so nice. We were on the first floor, and there was armchairs to sit in outside there and just enjoy the ocean breeze. Magical. The bar was quite cool as well, with live music. A pity that they stop playing at 19:00 and close the bar at 19:30 though. Breakfast was a lot of options, homemade cooking kinda vibe, we enjoyed it a lot. Parking was very convenient, I don’t understand the bad reviews about the distance. Guys, it’s literally 1 minutes walk. It’s good for you, just walk. It’s not gonna kill you. Strongly recommend!
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,172 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.

A
Alice
From
France
Amazing time at the Old Town Manor Cosy room, great breakfast, heartwarming welcome ! Many thanks!
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,041 reviews
Price from
US$289
1 night, 2 adults

Weatherstation Inn Circa 1911

Downtown Key West, Key West

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...

J
JT
From
United Kingdom
Everything. Breakfast were help yourself contintal. Good quality and lots of it. Location really good
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 262 reviews
Price from
US$199
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.

R
Radu
From
Netherlands
Location is perfect. Not on main and noisy street, but close enough to all shops and restaurants. Parking is possible and the private garden with pool is cozy and thoughtful decorated. Host is lovely and breakfast also possible.
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 320 reviews
Price from
US$549
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
Kathryn
From
Australia
Beautiful and historical. Rooms were stunning and so comfortable with all the amenities. The staff were so friendly and helpful and took the time to show me everything and answer any questions I had. Will definitely be back
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 206 reviews
Price from
US$219.45
1 night, 2 adults

Aquaria House -Pool & Boat Dock

Key West

Boasting air-conditioned accommodation with a private pool, Aquaria House -Pool & Boat Dock is situated in Key West.

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 5 reviews
Price from
US$918.85
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$918.85
1 night, 2 adults

Cloud Suite On Duval

Downtown Key West, Key West

Situated in the centre of Key West, less than 1 km from South Beach and a 1-minute walk from Duval Street, Cloud Suite On Duval offers free WiFi and air conditioning.

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 14 reviews
Price from
US$748.65
1 night, 2 adults

Sky Suite On Duval

Downtown Key West, Key West

Set in the centre of Key West, less than 1 km from South Beach and a 1-minute walk from Duval Street, Sky Suite On Duval offers free WiFi and air conditioning.

S
Stavroula
From
Canada
Hosts were SUPER nice and accommodating, location is ideal, and apartment was perfect! Would definitely stay here again.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 10 reviews
Price from
US$906.20
1 night, 2 adults
All holiday rentals in Key West

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

See all

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 335 reviews

Popular with guests booking holiday rentals in Key West

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

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 838 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 1,383 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,041 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 661 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 747 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 526 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,172 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 7.5
Good - What previous guests thought, 1,714 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$1,648.63 per night
Scored out of 10, guest rating 7.9
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$1,131.53 per night
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 2 reviews

Set in the centre of Key West, 700 metres from South Beach and 300 metres from Duval Street, Duval Street Suite w kitchen and shared heated pool offers free WiFi, a garden and air conditioning.

From US$372.49 per night
Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 4 reviews

Set in the centre of Key West, 700 metres from South Beach and 300 metres from Duval Street, Duval Street Suite overlooking Duval w parking and pool offers free WiFi, a garden and air conditioning.

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 795 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$336.38 per night
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 184 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 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$1,798.71 per night
Scored out of 10, guest rating 7.8
Good - What previous guests thought, 123 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$516.38 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, 467 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$443.60 per night
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$490.89 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 335 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$395.80 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 325 reviews

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

From US$565.88 per night
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 11 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...

Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 46 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, 690 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$472.50 per night
Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 50 reviews

Tortuga Suite at Sunrise Suites Resort - Heated Pool, Hot Tub & Free Parking is set in Key West, 6.5 km from Southernmost Point, 7.3 km from Ernest Hemingway Home and Museum, and 7.4 km from Duval...

From US$765.45 per night

Enjoy breakfast in Key West and nearby

Scored out of 10, guest rating 7.5
Good - What previous guests thought, 1,714 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$347.73 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.

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 8.9
Fabulous - What previous guests thought, 526 reviews

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.

From US$320.63 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.

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 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!

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

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, 44 reviews

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

From US$603.39 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$1,342.18 per night

Duval Dream Loft on Duval

Downtown Key West, Key West
Free cancellation options available
Scored out of 10, guest rating 7.3
Good - What previous guests thought, 24 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$1,224.57 per night

Curry House Room 6

Downtown Key West, Key West
Free cancellation options available
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$504.79 per night
Scored out of 10, guest rating 6.0
Pleasant - What previous guests thought, 3 reviews

Conveniently set in Key West, Classic King- Curry Mansion with Heated Pool! provides air-conditioned rooms, a garden and free WiFi.

Scored out of 10, guest rating 7.6
Good - What previous guests thought, 49 reviews

Conveniently located in Key West, King Suite Balcony - at James House offers air-conditioned rooms, a garden and free WiFi.

Scored out of 10, guest rating 5.3
Passable - What previous guests thought, 3 reviews

Well located in Key West, Classic King with Balcony at Curry Mansion provides air-conditioned rooms, a garden and free WiFi.

Scored out of 10, guest rating 7.2
Good - What previous guests thought, 8 reviews

Well situated in the centre of Key West, Deluxe Queen at the Curry Mansion - Parking & Heated Pool! offers air-conditioned rooms, a garden and free WiFi.

From US$544.64 per night

FAQ about holiday rentals in Key West

Holiday rentals that guests love in Key West

See all
Avg. price/night: US$640.13
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 295 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, 320 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, 320 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$640.13
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 295 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