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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, 1,382 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.

E
Elaine
From
Falkland Islands (Malvinas)
The room was spectacular and breakfast was delicious
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,173 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.

T
Tomáš
From
Slovakia
Helpful employees, pleasant furniture equipment, exceptional breakfast.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,041 reviews
Price from
US$229
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...

M
Michele
From
United States
Location location this was great you were a block maybe two away from Sloppy Joe's and Deval Street close to Mallory Square you are off the beaten path but close to everything I would recommend this it was wonderful I felt safe staying there after hours they lock the gate so you had a key to get in but I could walk back to my room feeling safe it was a wonderful place to stay the staff was wonderful this will be my new place every time I come to the Keys now which is once a year
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.

W
Werner Alberts
From
Isle of Man
The service of the staff is outstanding. They made us feel special and at home from the first minute. The house has a very interesting history and famous thrilling story but you need to hear it first hand. The rooms are large and very comfortable. All well airconditioned. The location is excellent and close to the main attractions. The breakfast are excellent with a wide selection. The selection of coffee is also excellent. Happy hour at 4pm is brilliant and the hosts are very generous with wine, beer , cake and other snacks. The splash pool was a life saver. The one day was 100+F and we spent 3 hours in the pool cooling down. It was such a social occasion with other guests.
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$747.50
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, 1,382 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.

E
Elaine
From
Falkland Islands (Malvinas)
The room was spectacular and breakfast was delicious
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,173 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.

T
Tomáš
From
Slovakia
Helpful employees, pleasant furniture equipment, exceptional breakfast.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,041 reviews
Price from
US$229
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...

M
Michele
From
United States
Location location this was great you were a block maybe two away from Sloppy Joe's and Deval Street close to Mallory Square you are off the beaten path but close to everything I would recommend this it was wonderful I felt safe staying there after hours they lock the gate so you had a key to get in but I could walk back to my room feeling safe it was a wonderful place to stay the staff was wonderful this will be my new place every time I come to the Keys now which is once a year
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.

W
Werner Alberts
From
Isle of Man
The service of the staff is outstanding. They made us feel special and at home from the first minute. The house has a very interesting history and famous thrilling story but you need to hear it first hand. The rooms are large and very comfortable. All well airconditioned. The location is excellent and close to the main attractions. The breakfast are excellent with a wide selection. The selection of coffee is also excellent. Happy hour at 4pm is brilliant and the hosts are very generous with wine, beer , cake and other snacks. The splash pool was a life saver. The one day was 100+F and we spent 3 hours in the pool cooling down. It was such a social occasion with other guests.
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$747.50
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, 836 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 1,382 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, 662 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 743 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 528 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,173 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

Highly rated holiday rentals in Key West and nearby

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$923.01 per night
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 8.8
Fabulous - What previous guests thought, 662 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.

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 8.6
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 8.9
Fabulous - What previous guests thought, 10 reviews

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

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, 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$1,647.34 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, 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$604.69 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

Nyah - Adult Exclusive

Downtown Key West, Key West
Free cancellation options available
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

Honey Bun Hideaway

Downtown Key West, Key West
Free cancellation options available
Scored out of 10, guest rating 7.0
Good - What previous guests thought, 1 review

Well situated in Key West, Honey Bun Hideaway offers air-conditioned rooms, a garden and free WiFi. The property is close to Mallory Square, Duval Street and Ernest Hemingway Home and Museum.

From US$541.35 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 7.2
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$577.82 per night

Seaport Suite

Downtown Key West, Key West
Free cancellation options available

Set in the centre of Key West, 400 metres from Simonton Street Beach and 500 metres from Key West Aquarium, Seaport Suite offers free WiFi, a garden and air conditioning.

From US$1,856.93 per night

Holiday Rentals with swimming pools in Key West and nearby

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 7.5
Good - What previous guests thought, 31 reviews

Boasting air-conditioned accommodation with a patio, The Trinidad -Pool & Parking is situated in Key West. Featuring a lift, this property also provides guests with an outdoor pool.

From US$796.50 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$749.93 per night

Boasting air-conditioned accommodation with a private pool, Waterlane House -Pool & Boat Dock is set in Stock Island.

From US$1,523.08 per night

Featuring air-conditioned accommodation with a private pool, Springtide House -Dock & Home w Pool is located in Stock Island.

From US$1,523.08 per night

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

From US$2,063.08 per night
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Boasting air-conditioned accommodation with a private pool, Mastway House -Pool & Dock! is set in Key West.

From US$1,523.08 per night

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...

Enjoy breakfast in Key West and nearby

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 8.9
Fabulous - What previous guests thought, 528 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!

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$1,158.69 per night
Scored out of 10, guest rating 7.0
Good - What previous guests thought, 4 reviews

Set 600 metres from South Beach and 500 metres from Ernest Hemingway Home and Museum in the centre of Key West, Duval Breeze by AvantStay Great Location Close to Beach Nightlife Shared Pool Week Long...

FAQ about holiday rentals in Key West

Holiday rentals that guests love in Key West

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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