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Holiday Rentals in Key West

Find the holiday rentals that appeal to you the most

The best holiday rentals in Key West

Check out our pick of great holiday rentals in Key West

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L'Habitation Guesthouse- Adult Exclusive

Downtown Key West, Key West

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

Y
YKuzin
From
Guyana
Very clean , all as expected , very friendly owners .
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,402 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, 1,168 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.

V
Veronika
From
Ukraine
it’s super unique, authentic and beautiful
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,047 reviews
Price from
US$289
1 night, 2 adults

The Casablanca Hotel

Downtown Key West, Key West

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

A
Andrew
From
United Kingdom
Super cute little hotel right in the heart of Duval street, but far enough from the Mallory Square end that it's not totally crazy outside. Tons of great restaurants and bars within a few blocks. Nice little pool and adjoining bar. Our room had a large deck with chairs that faced into some palm trees at the edge of the property. Really nice spot to read in the morning or just chill whenever.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 519 reviews
Price from
US$135
1 night, 2 adults

Key West Villas

Downtown Key West, Key West

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

G
Gintarė
From
Lithuania
Fabulous property! The stuff, communication via watsup is perfect, about happy hour, about breakfast and ect. In villa you will find everything you need and more. Best experience!
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 333 reviews
Price from
US$979
1 night, 2 adults

The Artist House

Downtown Key West, Key West

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

D
Dearbhla
From
Ireland
One word - WOW!! Absolutely loved our stay here and will be back! The rooms are massive for Key West with charming decor. Staff are incredible, so friendly and helpful. Fantastic complementary breakfast in the gorgeous garden. Can’t recommend this place highly enough!
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 197 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$1,404.15
1 night, 2 adults

Evershore House -Pool, Parking, Dock!

Key West

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

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 5 reviews
Price from
US$1,498.45
1 night, 2 adults

The Island Suite at KW Vacation

Downtown Key West, Key West

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

S
Siobhan
From
United Kingdom
Lovely suite in a very nice complex beautiful peaceful surroundings.
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 38 reviews
Price from
US$432
1 night, 2 adults

The Bartlum-Luxurious Studio

Downtown Key West, Key West

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

S
SIqintana
From
United States
Offering free parasol/shade umbrella service is great.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 46 reviews
Price from
US$262.89
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 8.7
Fabulous - What previous guests thought, 702 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,402 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 324 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 519 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 863 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 763 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,168 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,047 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 653 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 7.4
Good - What previous guests thought, 1,739 reviews

Highly rated holiday rentals in Key West and nearby

Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 469 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$417.64 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 800 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$280.13 per night
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 187 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, 391 reviews

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

From US$363.04 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 653 reviews

Set in Key West, less than 1 km from South Beach, La Pensione Inn - Adult Exclusive offers accommodation with an outdoor swimming pool, free private parking, a shared lounge and a terrace.

From US$246.38 per night
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 15 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...

From US$653.91 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 863 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$358.88 per night
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 862 reviews

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

From US$349.49 per night

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$1,547.72 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!

From US$1,132.82 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.

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$547.48 per night

Set in the centre of Key West, 1 km from Simonton Street Beach and 800 metres from Duval Street, Curry House - Room 2 offers free WiFi, a garden and air conditioning.

From US$522.79 per night
Scored out of 10, guest rating 6.4
Pleasant - What previous guests thought, 7 reviews

Situated in the centre of Key West, 1 km from Simonton Street Beach, Curry House - Room 1 features air-conditioned rooms and free WiFi.

From US$537.02 per night
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 261 reviews

Set within 500 metres of Key West Aquarium, Weatherstation Inn Circa 1911 is an adult-only bed and breakfast in Key West and features a number of amenities including an outdoor swimming pool and a...

From US$223.88 per night
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 299 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$471.38 per night

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, 45 reviews

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

From US$581.40 per night

Duval Dream Loft on Duval

Downtown Key West, Key West
Free cancellation options available
Scored out of 10, guest rating 7.1
Good - What previous guests thought, 26 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$1,044.10 per night

Nyah - Adult Exclusive

Downtown Key West, Key West
Free cancellation options available
Scored out of 10, guest rating 7.4
Good - What previous guests thought, 1,739 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$175.60 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.

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$1,004.91 per night
Scored out of 10, guest rating 7.0
Good - What previous guests thought, 2 reviews

Located in the centre of Key West, 400 metres from Simonton Street Beach and 500 metres from Key West Aquarium, The Mesa House-Close to Duval! offers free WiFi and air conditioning.

From US$1,402.28 per night
Scored out of 10, guest rating 7.4
Good - What previous guests thought, 44 reviews

In the centre of Key West, located within a short distance of Simonton Street Beach and Key West Aquarium, Mesa House, Uno-Perfect Location offers free WiFi, air conditioning and household amenities...

From US$622.86 per night
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 9 reviews

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

Enjoy breakfast in Key West and nearby

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 324 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$307.60 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.

Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 13 reviews

Situated in the centre of Key West, 700 metres from South Beach and 200 metres from Ernest Hemingway Home and Museum, Just steps to Duval- Sleeps 10- Heated Pool House offers free WiFi, a garden and...

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 8.5
Very good - What previous guests thought, 17 reviews

Located in the centre of Key West, 700 metres from South Beach and 400 metres from Duval Street, Road's End offers free WiFi, a garden and air conditioning.

From US$622.86 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.

FAQ about holiday rentals in Key West

Holiday rentals that guests love in Key West

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Avg. price/night: US$471.38
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 299 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$246.38
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 333 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$246.38
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 333 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$471.38
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 299 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
gogless