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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...

J
Jeannine
From
Austria
The guesthouse is such a beautiful house! we loved our room and it was very comfortable! the breakfast had everything we needed - even almond milk! the location is perfect to explore everything in key west! just around the corner of the duval street and still very quiet!
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,422 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.

a
andrea
From
Italy
Location is perfect, close to the nightlife and far from it at the same time. lovely house for lovely persons.
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,176 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.

d
daniel
From
United States
Stunning courtyard, delicious breakfast, quiet but right around the corner from bars, restaurants
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,059 reviews
Price from
US$289
1 night, 2 adults

Grand Marina Suite -Waterfront Condo

Key West

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.

K
Kim
From
United States
Large room for a family, has everything you need. Lovely place with a wonderful pool with a beautiful view.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 124 reviews
Price from
US$420.21
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.

N
Nadia
From
Austria
we loved it, very beautiful room, staff extremely helpful and accommodating, location is beautiful, pool is lovely!! highly recommend!!
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 523 reviews
Price from
US$145
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.

W
Werner Alberts
From
Isle of Man
The service of the staff is outstanding. They made us feel special and at home from the first minute. The house has a very interesting history and famous thrilling story but you need to hear it first hand. The rooms are large and very comfortable. All well airconditioned. The location is excellent and close to the main attractions. The breakfast are excellent with a wide selection. The selection of coffee is also excellent. Happy hour at 4pm is brilliant and the hosts are very generous with wine, beer , cake and other snacks. The splash pool was a life saver. The one day was 100+F and we spent 3 hours in the pool cooling down. It was such a social occasion with other guests.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 187 reviews
Price from
US$219.45
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

Keys Please!

Downtown Key West, Key West

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.

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 6 reviews
Price from
US$757.85
1 night, 2 adults

The St Martin -Hot Tub & Pool

Key West

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.

g
gary
From
United Kingdom
Tennis court nearby and decent pool
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 16 reviews
Price from
US$269.10
1 night, 2 adults

The Exuma Cay -Pool View & Parking

Key West

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.

N
Nina
From
Netherlands
The apartment was spacious, clean and cozy. The beds, even the sofa bed, were comfortable. Two bathrooms with very nice showers. The kitchen was fully equipped with plenty of everything. This is very convenient for a family with food allergies since this actually allows for cooking your own safe meal. In our experience, this is exceptional; often times when kitchens are described as fully equipped, they are not. This was a nice exception. Excellent washer/drying combination. Nice pool, sufficient towels. Staff was very helpful: we requested extra dishwashing powder since we did our own cooking and it was brought over the next day. We had the most excellent stay!
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 33 reviews
Price from
US$322
1 night, 2 adults
All holiday rentals in Key West

Most booked holiday rentals in Key West and surroundings in the past month

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

  • Scored out of 10, guest rating 8.0
    Very 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$1,056.49 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$1,135.41 per night
  • Scored out of 10, guest rating 8.6
    Fabulous - What previous guests thought, 26 reviews

    In the heart of Key West, set within a short distance of South Beach and Ernest Hemingway Home and Museum, Sea Breeze -Great Location!

    From US$800.10 per night
  • Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 659 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$302.63 per night
  • Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 865 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$403.88 per night
  • The Grand Guesthouse

    Downtown Key West, Key West
    Free cancellation options available
    Scored out of 10, guest rating 8.6
    Fabulous - What previous guests thought, 859 reviews

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

    From US$477.97 per night
  • Curry House Room 6

    Downtown Key West, Key West
    Free cancellation options available
    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$614.76 per night
  • Curry House - Room 2

    Downtown Key West, Key West
    Free cancellation options available

    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$480.09 per night

Enjoy breakfast in Key West and nearby

  • Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 1,276 reviews

    Offering 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$325.13 per night
  • Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 404 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, 312 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$336.38 per night
  • Scored out of 10, guest rating 7.4
    Good - What previous guests thought, 1,768 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$276.85 per night
  • Scored out of 10, guest rating 8.7
    Fabulous - What previous guests thought, 743 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$258.75 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 7.9
    Good - What previous guests thought, 25 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 8.2
    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...

Highly rated holiday rentals in Key West and nearby

  • Scored out of 10, guest rating 8.1
    Very good - What previous guests thought, 472 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$430.05 per night
  • Scored out of 10, guest rating 9.2
    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$429.30 per night
  • Scored out of 10, guest rating 8.4
    Very good - What previous guests thought, 302 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$415.13 per night
  • Scored out of 10, guest rating 8.0
    Very good - What previous guests thought, 24 reviews

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

    From US$541.35 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.

    From US$342.86 per night
  • Scored out of 10, guest rating 8.1
    Very good - What previous guests thought, 39 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$344.18 per night
  • Scored out of 10, guest rating 8.5
    Very good - What previous guests thought, 58 reviews

    Boasting air-conditioned accommodation with a balcony, Atlantic Ocean View is located in Key West. Featuring a lift, this property also has a restaurant and an outdoor pool.

  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 21 reviews

    Located in Key West in the Florida region, Sunrise Suites Big Kahuna Suite #202 has a balcony. Guests can benefit from a terrace and an outdoor pool. The apartment features a hot tub and a lift.

    From US$694.74 per night

Holiday Rentals with swimming pools in Key West and nearby

  • Scored out of 10, guest rating 7.7
    Good - What previous guests thought, 122 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$291.38 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$502.09 per night
  • Scored out of 10, guest rating 8.0
    Very good - What previous guests thought, 3 reviews

    Situated within the Downtown Key West district in Key West, Banana Split has air conditioning, a patio, and city views.

    From US$774.28 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$521.94 per night
  • Scored out of 10, guest rating 7.2
    Good - What previous guests thought, 8 reviews

    Located in a central area of Key West, 400 metres from Simonton Street Beach, Sweet Caroline provides air-conditioned accommodation with free WiFi and a TV.

    From US$1,272.26 per night
  • Scored out of 10, guest rating 7.0
    Good - What previous guests thought, 2 reviews

    In a prime location in the centre of Key West, Key Lime Cottage offers air-conditioned rooms, a garden and free WiFi.

    From US$633.21 per night
  • 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.

    From US$494.78 per night
  • Scored out of 10, guest rating 6.1
    Pleasant - What previous guests thought, 34 reviews

    This boutique hotel offers a landscaped tropical garden and a lagoon-style dipping pool. It is located in the Casa Marina Area of Key West, Florida, only 3 blocks from the beach.

    From US$264.77 per night

FAQ about holiday rentals in Key West

Holiday rentals that guests love in Key West

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  • Avg. price/night: US$415.13
    Scored out of 10, guest rating 8.4
    Very good - What previous guests thought, 302 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$471.38
    Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 345 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$471.38
    Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 345 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$415.13
    Scored out of 10, guest rating 8.4
    Very good - What previous guests thought, 302 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