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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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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...

L
Lisandre
From
Canada
Awesome stay! We were welcomed by Foster who gave us great recommandations and was really friendly! The location was perfect!
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.

J
Janno
From
Estonia
Supreme location if you travel with kids and prefer a less noisy area of the main street. It was dead quiet during nighttime. It is at the end (or beginning) of Duval street and yet it is well close enough to all the Key West action. Staff was extraordinarily helpful and rooms were very nice. Very easy parking just next to the rooms. Breakfast was good and we liked the setup where you get your coffee and food and then just take it outside to enjoy your breakfast with a nice morning breeze from ocean which is just 100 meters away. I think the whole concept of this establishment gives you a really nice understanding of "Key West" way of living. Really good :)
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.

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, 1,045 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...

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.

A
Alex
From
United Kingdom
Heather and Kevin were so helpful and welcoming. The location is perfect. The rooms are comfortable and very tidy. No complaints.
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, 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$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$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...

L
Lisandre
From
Canada
Awesome stay! We were welcomed by Foster who gave us great recommandations and was really friendly! The location was perfect!
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.

J
Janno
From
Estonia
Supreme location if you travel with kids and prefer a less noisy area of the main street. It was dead quiet during nighttime. It is at the end (or beginning) of Duval street and yet it is well close enough to all the Key West action. Staff was extraordinarily helpful and rooms were very nice. Very easy parking just next to the rooms. Breakfast was good and we liked the setup where you get your coffee and food and then just take it outside to enjoy your breakfast with a nice morning breeze from ocean which is just 100 meters away. I think the whole concept of this establishment gives you a really nice understanding of "Key West" way of living. Really good :)
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.

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, 1,045 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...

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.

A
Alex
From
United Kingdom
Heather and Kevin were so helpful and welcoming. The location is perfect. The rooms are comfortable and very tidy. No complaints.
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, 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$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$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, 336 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 861 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, 1,383 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,045 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, 743 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 533 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, 1,709 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, 533 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
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$1,673.21 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 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$1,127.64 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...

From US$1,791.51 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, 43 reviews

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

From US$661.61 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$2,701.74 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.

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.

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$505.13 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 9.3
Superb - What previous guests thought, 30 reviews

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

From US$510.30 per night
Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 13 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 8.8
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$1,943.83 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 836 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
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 67 reviews

Offering a year-round outdoor pool and terrace, this adult-only (21 years +) Marreros Guest Mansion is set in the Duval district in Key West. Duval Street is a 1 minute walk from the property.

From US$590.63 per night

Enjoy breakfast in Key West and nearby

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 861 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, 336 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$438.75 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, 685 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, 1,103 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$325.13 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.

Holiday Rentals with swimming pools in Key West and nearby

In the heart of Key West, set within a short distance of South Beach and Ernest Hemingway Home and Museum, Southern Palms offers free WiFi, air conditioning and household amenities such as a microwave...

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 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 7.9
Good - What previous guests thought, 23 reviews

Ideally situated in the centre of Key West, Creme Brulee Suite features air-conditioned rooms, a garden and free WiFi.

From US$626.74 per night
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$502.16 per night
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 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$488.88 per night
Scored out of 10, guest rating 4.7
Disappointing - What previous guests thought, 4 reviews

Attractively located in Key West, Deluxe King - Curry Mansion with Pool! features air-conditioned rooms, a garden and free WiFi.

FAQ about holiday rentals in Key West

Holiday rentals that guests love in Key West

See all
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