Holiday Rentals in Key West
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The best 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.
Grand Marina Suite -Waterfront Condo
Located in Key West, 9.1 km from Ernest Hemingway Home and Museum and 9.2 km from Duval Street, Grand Marina Suite -Waterfront Condo offers a garden and air conditioning.
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.
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.
Evershore House -Pool, Parking, Dock!
Featuring air-conditioned accommodation with a private pool, Evershore House -Pool, Parking, Dock! is located in Key West.
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.
The St Martin -Hot Tub & Pool
Boasting air-conditioned accommodation with a patio, The St Martin -Hot Tub & Pool is situated in Key West. Both free WiFi and parking on-site are accessible at the holiday home free of charge.
The Exuma Cay -Pool View & Parking
Boasting air-conditioned accommodation with a patio, The Exuma Cay -Pool View & Parking is situated in Key West. Featuring a lift, this property also provides guests with an outdoor pool.
Most booked holiday rentals in Key West and surroundings in the past month
Popular with guests booking holiday rentals in Key West
Scored out of 10, guest rating 8.8Fabulous - What previous guests thought, 1,274 reviewsPopular with guests booking holiday rentals in Key West
Scored out of 10, guest rating 8.9Fabulous - What previous guests thought, 816 reviewsPopular with guests booking holiday rentals in Key West
Scored out of 10, guest rating 9.1Superb - What previous guests thought, 1,059 reviewsPopular with guests booking holiday rentals in Key West
Scored out of 10, guest rating 8.8Fabulous - What previous guests thought, 1,163 reviewsPopular with guests booking holiday rentals in Key West
Scored out of 10, guest rating 9.0Superb - What previous guests thought, 524 reviewsPopular with guests booking holiday rentals in Key West
Scored out of 10, guest rating 8.8Fabulous - What previous guests thought, 865 reviewsPopular with guests booking holiday rentals in Key West
Scored out of 10, guest rating 8.8Fabulous - What previous guests thought, 312 reviewsPopular with guests booking holiday rentals in Key West
Scored out of 10, guest rating 9.1Superb - What previous guests thought, 1,422 reviewsPopular with guests booking holiday rentals in Key West
Scored out of 10, guest rating 7.4Good - What previous guests thought, 1,768 reviewsPopular with guests booking holiday rentals in Key West
Scored out of 10, guest rating 9.3Superb - What previous guests thought, 1,176 reviews
Highly rated holiday rentals in Key West and nearby
Old Town Suites
Downtown Key West, Key West8.0+ review scoreScored out of 10, guest rating 8.1Very good - What previous guests thought, 473 reviewsLocated 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$685.15 per nightNew Casa Caribe by Brightwild- Two-Story Condo Rooftop Pool
Downtown Key West, Key West8.0+ review scoreScored out of 10, guest rating 8.0Very good - What previous guests thought, 14 reviewsLocated 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$1,802.98 per nightSea Breeze -Great Location!
Downtown Key West, Key West8.0+ review scoreScored out of 10, guest rating 8.6Fabulous - What previous guests thought, 26 reviewsIn the heart of Key West, set within a short distance of South Beach and Ernest Hemingway Home and Museum, Sea Breeze -Great Location!
Duval House
Downtown Key West, Key West8.0+ review scoreScored out of 10, guest rating 8.9Fabulous - What previous guests thought, 816 reviewsLocated 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$448.88 per night- Scored out of 10, guest rating 8.9Fabulous - What previous guests thought, 188 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$248.92 per night The Conch House Heritage Inn
Downtown Key West, Key West8.0+ review scoreScored out of 10, guest rating 9.2Superb - What previous guests thought, 30 reviewsThis adult-only Conch House Heritage Inn offers accommodation in Key West with breakfast included and complimentary mimosas.
From US$388.80 per nightCourtney's Place Historic Cottages & Inns
Downtown Key West, Key West8.0+ review scoreScored out of 10, guest rating 8.8Fabulous - What previous guests thought, 1,274 reviewsOffering an outdoor pool, this historic Key West property is just 1 minutes’ walk from Duval Street. Free WiFi and a light continental breakfast are provided daily to all guests.
From US$426.38 per nightCaribbean House
Downtown Key West, Key West8.0+ review scoreScored out of 10, guest rating 8.8Fabulous - What previous guests thought, 404 reviewsFeaturing free WiFi throughout this adult-only property, Caribbean House offers accommodation in Key West.
From US$392.29 per night
These holiday rentals in Key West and nearby have options with free cancellation
NEW! Villa Positano - Duval Square Condo, Pool, Hot Tub & Parking
Downtown Key West, Key WestFree cancellation options availableScored out of 10, guest rating 5.0Passable - What previous guests thought, 2 reviewsSet in the centre of Key West, 600 metres from South Beach and 500 metres from Ernest Hemingway Home and Museum, NEW!
From US$1,720.18 per nightCoconut Palm
Downtown Key West, Key WestFree cancellation options availableScored out of 10, guest rating 5.3Passable - What previous guests thought, 3 reviewsRight 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
Downtown Key West, Key WestFree cancellation options availableScored out of 10, guest rating 7.8Good - What previous guests thought, 45 reviewsLocated within the Downtown Key West district in Key West, Traveler's Palm has air conditioning, a patio, and city views.
From US$992.81 per nightLa Pensione Inn - Adult Exclusive
Downtown Key West, Key WestFree cancellation options availableScored out of 10, guest rating 8.8Fabulous - What previous guests thought, 658 reviewsSet 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 nightAlexander Palms Court - No Hidden Resort Fees!
Downtown Key West, Key WestFree cancellation options availableScored out of 10, guest rating 8.8Fabulous - What previous guests thought, 865 reviewsAlexander 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$235.13 per nightThe Grand Guesthouse
Downtown Key West, Key WestFree cancellation options availableScored out of 10, guest rating 8.6Fabulous - What previous guests thought, 860 reviewsThis all-adult bed and breakfast is within a 10-minute walk of Duval Street and the Atlantic Ocean.
From US$404.22 per nightCurry House Room 6
Downtown Key West, Key WestFree cancellation options availableScored out of 10, guest rating 7.0Good - What previous guests thought, 7 reviewsSituated 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$820.46 per nightCurry House - Room 2
Downtown Key West, Key WestFree cancellation options availableSet 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$711.68 per night
Holiday Rentals with swimming pools in Key West and nearby
Southern Palms
Downtown Key West, Key WestSwimming poolIn 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
Downtown Key West, Key WestSwimming poolScored out of 10, guest rating 7.7Good - What previous guests thought, 123 reviewsCentrally 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$313.88 per night- Scored out of 10, guest rating 8.9Fabulous - What previous guests thought, 77 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$572.63 per night Curry House - Room 1
Downtown Key West, Key WestSwimming poolScored out of 10, guest rating 6.4Pleasant - What previous guests thought, 7 reviewsSituated 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$714.26 per night- Scored out of 10, guest rating 8.9Fabulous - What previous guests thought, 258 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$505.13 per night Rose Lane Villas
Downtown Key West, Key WestSwimming poolScored out of 10, guest rating 8.4Very good - What previous guests thought, 301 reviewsLocated 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$415.13 per nightNyah - Adult Exclusive
Downtown Key West, Key WestSwimming poolScored out of 10, guest rating 7.4Good - What previous guests thought, 1,768 reviewsThis 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$308.60 per nightCreme Brulee Suite
Downtown Key West, Key WestSwimming poolScored out of 10, guest rating 8.0Very good - What previous guests thought, 24 reviewsIdeally situated in the centre of Key West, Creme Brulee Suite features air-conditioned rooms, a garden and free WiFi.
From US$809.16 per night
Enjoy breakfast in Key West and nearby
Key West Bed and Breakfast
Downtown Key West, Key WestBreakfast optionsScored out of 10, guest rating 8.8Fabulous - What previous guests thought, 312 reviewsKey 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$302.63 per nightThe Garden House
Downtown Key West, Key WestBreakfast optionsScored out of 10, guest rating 8.8Fabulous - What previous guests thought, 355 reviewsWell located in Key West, The Garden House provides express check-in and check-out and private parking.
Westwinds Inn
Downtown Key West, Key WestBreakfast optionsScored out of 10, guest rating 8.7Fabulous - What previous guests thought, 743 reviewsWithin 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$388.13 per nightAuthors Key West Guesthouse
Key WestBreakfast optionsScored out of 10, guest rating 8.8Fabulous - What previous guests thought, 1,163 reviewsFeaturing 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$167.63 per nightParadise Suite
Downtown Key West, Key WestBreakfast optionsParadise 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
Downtown Key West, Key WestBreakfast optionsScored out of 10, guest rating 7.9Good - What previous guests thought, 25 reviewsBoasting 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 8.2Very 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...
FAQ about holiday rentals in Key West
Holiday rentals that guests love in Key West
- Avg. price/night: US$415.13Scored out of 10, guest rating 8.4Very good - What previous guests thought, 301 reviewsbest location!! plenty of space for the family!! i will surely come back and stay the villas!!Guest review byAilenFamily with young children
- Avg. price/night: US$336.38Scored out of 10, guest rating 9.7Exceptional - What previous guests thought, 346 reviewsEverything was wonderful. The villas had everything you needed to make your trip enjoyable. Looking forward to going back again soon.Guest review byericaGroup
- Avg. price/night: US$336.38Scored out of 10, guest rating 9.7Exceptional - What previous guests thought, 346 reviewsPerfect 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 byThomasGroup
- Avg. price/night: US$415.13Scored out of 10, guest rating 8.4Very good - What previous guests thought, 301 reviewsAbsolutely 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 bylisaSolo traveller
