Holiday Rentals in Key West
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Top picks for Key West hotels
Explore our most popular hotels in Key West
- Scored out of 10, guest rating 8.8Fabulous - What previous guests thought, 336 reviewsFromUS$1761 night, 2 adults
- Scored out of 10, guest rating 9.2Superb - What previous guests thought, 1,383 reviewsFromUS$2191 night, 2 adults
- Scored out of 10, guest rating 8.9Fabulous - What previous guests thought, 1,269 reviewsFromUS$2491 night, 2 adults
- Scored out of 10, guest rating 8.5Very good - What previous guests thought, 296 reviewsFromUS$3141 night, 2 adults
- Scored out of 10, guest rating 9.1Superb - What previous guests thought, 1,045 reviewsFromUS$2291 night, 2 adults
- Scored out of 10, guest rating 8.9Fabulous - What previous guests thought, 533 reviewsFromUS$1451 night, 2 adults
- Scored out of 10, guest rating 8.8Fabulous - What previous guests thought, 790 reviewsFromUS$1391 night, 2 adults
- Scored out of 10, guest rating 9.4Superb - What previous guests thought, 206 reviewsFromUS$2191 night, 2 adults
- Scored out of 10, guest rating 8.8Fabulous - What previous guests thought, 1,103 reviewsFromUS$1491 night, 2 adults
- Scored out of 10, guest rating 9.0Superb - What previous guests thought, 262 reviewsFromUS$1991 night, 2 adults
- Scored out of 10, guest rating 8.8Fabulous - What previous guests thought, 325 reviewsFromUS$1271 night, 2 adults
- Scored out of 10, guest rating 8.8Fabulous - What previous guests thought, 836 reviewsFromUS$1891 night, 2 adults
- Scored out of 10, guest rating 8.7Fabulous - What previous guests thought, 664 reviewsFromUS$1701 night, 2 adults
- Scored out of 10, guest rating 9.3Superb - What previous guests thought, 30 reviewsFromUS$2381 night, 2 adults
- Scored out of 10, guest rating 7.5Good - What previous guests thought, 1,709 reviewsFromUS$1691 night, 2 adults
- Scored out of 10, guest rating 7.8Good - What previous guests thought, 123 reviewsFromUS$1991 night, 2 adults
- Scored out of 10, guest rating 8.1Very good - What previous guests thought, 47 reviewsFromUS$2561 night, 2 adults
- Scored out of 10, guest rating 8.7Fabulous - What previous guests thought, 685 reviewsFromUS$2451 night, 2 adults
- Scored out of 10, guest rating 9.3Superb - What previous guests thought, 39 reviewsFromUS$3201 night, 2 adults
- Scored out of 10, guest rating 8.3Very good - What previous guests thought, 12 reviewsFromUS$2441 night, 2 adults
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L'Habitation Guesthouse- Adult Exclusive
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...
Southernmost Point Guest House & Garden Bar
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.
Old Town Manor
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.
Weatherstation Inn Circa 1911
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...
Key West Villas
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.
The Artist House
This historical Key West bed and breakfast is 1 mile from the Southernmost Point and 3 minute’s walk from iconic Duval Street.
Aquaria House -Pool & Boat Dock
Boasting air-conditioned accommodation with a private pool, Aquaria House -Pool & Boat Dock is situated in Key West.
Evershore House -Pool, Parking, Dock!
Featuring air-conditioned accommodation with a private pool, Evershore House -Pool, Parking, Dock! is located in Key West.
Cloud Suite On Duval
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.
Sky Suite On Duval
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.
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
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...
Southernmost Point Guest House & Garden Bar
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.
Old Town Manor
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.
Weatherstation Inn Circa 1911
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...
Key West Villas
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.
The Artist House
This historical Key West bed and breakfast is 1 mile from the Southernmost Point and 3 minute’s walk from iconic Duval Street.
Aquaria House -Pool & Boat Dock
Boasting air-conditioned accommodation with a private pool, Aquaria House -Pool & Boat Dock is situated in Key West.
Evershore House -Pool, Parking, Dock!
Featuring air-conditioned accommodation with a private pool, Evershore House -Pool, Parking, Dock! is located in Key West.
Cloud Suite On Duval
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.
Sky Suite On Duval
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.
Most booked holiday rentals in Key West and surroundings in the past month
Popular with guests booking holiday rentals in Key West
Popular with guests booking holiday rentals in Key West
Popular with guests booking holiday rentals in Key West
Popular with guests booking holiday rentals in Key West
Popular with guests booking holiday rentals in Key West
Popular with guests booking holiday rentals in Key West
Popular with guests booking holiday rentals in Key West
Popular with guests booking holiday rentals in Key West
Popular with guests booking holiday rentals in Key West
Popular with guests booking holiday rentals in Key West
These holiday rentals in Key West and nearby have options with free cancellation
The Casablanca Hotel
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.
Casa Key West-Pool & Free Parking
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...
NEW! Villa Positano - Duval Square Condo, Pool, Hot Tub & Parking
Set in the centre of Key West, 600 metres from South Beach and 500 metres from Ernest Hemingway Home and Museum, NEW!
New Casa Caribe by Brightwild- Two-Story Condo Rooftop Pool
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...
Coconut Palm
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...
Traveler's Palm
Located within the Downtown Key West district in Key West, Traveler's Palm has air conditioning, a patio, and city views.
Contra House -Luxury Home With Pool
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.
La Pensione Inn - Adult Exclusive
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
Old Town Suites
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.
Duval House
Located centrally on lively Duval Street, Duval House offers a continental breakfast that includes Belgian waffles. The 7 Caribbean-style buildings offer free WiFi.
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.
The Conch House Heritage Inn
This adult-only Conch House Heritage Inn offers accommodation in Key West with breakfast included and complimentary mimosas.
Key Lime Calypso
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.
Keys Please!
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.
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.
Marreros Guest Mansion - Adult Only
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.
Enjoy breakfast in Key West and nearby
The Grand Guesthouse
This all-adult bed and breakfast is within a 10-minute walk of Duval Street and the Atlantic Ocean.
Key West Bed and Breakfast
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.
The Garden House
Well located in Key West, The Garden House provides express check-in and check-out and private parking.
Nyah - Adult Exclusive
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.
Westwinds Inn
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.
Authors Key West Guesthouse
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.
Paradise Suite
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.
Hemingway's View
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
Southern Palms
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...
Kona Kai Oasis
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.
Rose Lane Villas
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.
Creme Brulee Suite
Ideally situated in the centre of Key West, Creme Brulee Suite features air-conditioned rooms, a garden and free WiFi.
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.
Conveniently located in Key West, King Suite Balcony - at James House offers air-conditioned rooms, a garden and free WiFi.
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.
Attractively located in Key West, Deluxe King - Curry Mansion with Pool! features air-conditioned rooms, a garden and free WiFi.
