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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...

P
Peter
From
Norway
Very nice staff and good communication. We came early to Key West, they sent us a message on booking as soon as our room was ready. There was a cute breakfast with nice options, we especially enjoyed the pastries and coffee from local vendors. The thing we were very surprised by, was the happy hour in the afternoon, when there was some vodka and cranberry out for us to enjoy. Well done!
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.

c
cynthia
From
Cayman Islands
Very spacious and staff were extremely helpful and courteous.
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,170 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.

E
Eva
From
Austria
Wonderful garden, room in typical style, perfect site, near center,
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,044 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...

K
Kateryna
From
Ukraine
A lovely hotel in a great location, with very spacious rooms (at least the one I stayed in). The breakfast is simple but tasty, and the staff are very polite and friendly.
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.

a
anne
From
Switzerland
If I could give more than 10 I would! Everything was perfect: the location (in the heart of Key West, parking space available), the rooms (they’re even nicer as on the homepage), the poolside.. everything was so tasteful and clean. And of course the hosts ! They make everything to make you feel home. Snacks and drinks available all day long, happy hour every day and the bottle of wine offered upon arrival!! We just can strongly recommend this lovely place.
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 318 reviews
Price from
US$449
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.

S
Sophie
From
United Kingdom
Everything was fantastic! A very quirky guesthouse. The turret suite was perfect for a family of 4 and the balcony was an added bonus. The complementary breakfast was lovely and the happy hour is a great idea, giving chance to chat to other guests. Jess and Shaun were really hospitable and couldn’t really have done any more.
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 208 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$670.45
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$910.80
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...

P
Peter
From
Norway
Very nice staff and good communication. We came early to Key West, they sent us a message on booking as soon as our room was ready. There was a cute breakfast with nice options, we especially enjoyed the pastries and coffee from local vendors. The thing we were very surprised by, was the happy hour in the afternoon, when there was some vodka and cranberry out for us to enjoy. Well done!
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.

c
cynthia
From
Cayman Islands
Very spacious and staff were extremely helpful and courteous.
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,170 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.

E
Eva
From
Austria
Wonderful garden, room in typical style, perfect site, near center,
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,044 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...

K
Kateryna
From
Ukraine
A lovely hotel in a great location, with very spacious rooms (at least the one I stayed in). The breakfast is simple but tasty, and the staff are very polite and friendly.
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.

a
anne
From
Switzerland
If I could give more than 10 I would! Everything was perfect: the location (in the heart of Key West, parking space available), the rooms (they’re even nicer as on the homepage), the poolside.. everything was so tasteful and clean. And of course the hosts ! They make everything to make you feel home. Snacks and drinks available all day long, happy hour every day and the bottle of wine offered upon arrival!! We just can strongly recommend this lovely place.
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 318 reviews
Price from
US$449
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.

S
Sophie
From
United Kingdom
Everything was fantastic! A very quirky guesthouse. The turret suite was perfect for a family of 4 and the balcony was an added bonus. The complementary breakfast was lovely and the happy hour is a great idea, giving chance to chat to other guests. Jess and Shaun were really hospitable and couldn’t really have done any more.
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 208 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$670.45
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$910.80
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, 337 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 860 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, 1,044 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 664 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 744 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 534 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,170 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 7.5
Good - What previous guests thought, 1,709 reviews

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

The Casablanca Hotel

Downtown Key West, Key West
Free cancellation options available
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 534 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$410.63 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, 42 reviews

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

From US$652.56 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$2,660.34 per night
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 664 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.

Sky Loft in Key West

Downtown Key West, Key West
Free cancellation options available
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 17 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...

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$1,179.17 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$1,088.35 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 838 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$482.63 per night

Enjoy breakfast in Key West and nearby

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 790 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$392.63 per night
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 185 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 8.6
Fabulous - What previous guests thought, 860 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, 337 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$484 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$435.38 per night
Scored out of 10, guest rating 7.5
Good - What previous guests thought, 1,709 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
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 684 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$466.88 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 1,105 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$291.38 per night

Holiday Rentals with swimming pools in Key West and nearby

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$482.63 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$503.49 per night
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 296 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$786.38 per night
Scored out of 10, guest rating 3.5
Poor - What previous guests thought, 2 reviews

Ideally set in Key West, Sugar Pie Suite offers air-conditioned rooms, a garden and free WiFi.

From US$603.45 per night
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 13 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 8.1
Very good - What previous guests thought, 47 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.

From US$495.52 per night
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$483.57 per night
Scored out of 10, guest rating 7.4
Good - What previous guests thought, 91 reviews

Located in Key West, this Florida hotel is 1.6 km from the shopping, entertainment, and nightlife of Duval Street. Features include a shared outdoor pool with a waterfall and free property-wide WiFi.

From US$358.88 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, 466 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.

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$1,069.59 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$863.78 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 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.

Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 6 reviews

Featuring air-conditioned accommodation with a terrace, Julia Whitehead Guest Suites is located in Key West. This holiday home also features a restaurant.

Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 9 reviews

Mermaid's Retreat 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$786.38
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 296 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$842.63
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 318 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$842.63
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 318 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$786.38
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 296 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