The 10 best holiday rentals in Key West, USA | Booking.com
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Holiday Rentals in Key West

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The best holiday rentals in Key West

Check out our pick of great holiday rentals in Key West

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

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Enjoy breakfast in Key West and nearby

  • Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 191 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.

  • Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 32 reviews

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

  • Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 1,274 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$572.63 per night
  • Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 407 reviews

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

  • 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$325.13 per night
  • Scored out of 10, guest rating 9.0
    Superb - 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.

  • Scored out of 10, guest rating 8.6
    Fabulous - What previous guests thought, 865 reviews

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

  • Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 308 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.

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$1,033.94 per night
  • Scored out of 10, guest rating 8.5
    Very good - What previous guests thought, 17 reviews

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

    From US$928.18 per night
  • 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$1,597.28 per night
  • Scored out of 10, guest rating 8.0
    Very good - What previous guests thought, 14 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 9.0
    Superb - What previous guests thought, 16 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...

  • Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 260 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$392.63 per night
  • Scored out of 10, guest rating 8.4
    Very good - What previous guests thought, 298 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.

  • Scored out of 10, guest rating 8.0
    Very good - What previous guests thought, 22 reviews

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

    From US$725.06 per night

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

  • Scored out of 10, guest rating 7.5
    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...

  • 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$1,595.98 per night

  • Coconut Palm

    Downtown Key West, Key West
    Free cancellation options available
    Scored out of 10, guest rating 5.3
    Passable - What previous guests thought, 3 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$2,197.74 per night

  • Traveler's Palm

    Downtown Key West, Key West
    Free cancellation options available
    Scored out of 10, guest rating 7.9
    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.

  • The Collins on Duval

    Downtown Key West, Key West
    Free cancellation options available
    Scored out of 10, guest rating 6.4
    Pleasant - What previous guests thought, 6 reviews

    In the heart of Key West, set within a short distance of Simonton Street Beach and Duval Street, The Collins on Duval offers free WiFi, air conditioning and household amenities such as a fridge and...

    From US$1,649.58 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, 27 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$1,518 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.

  • 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$577.13 per night

FAQ about holiday rentals in Key West

Holiday rentals that guests love in Key West

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  • Rose Lane Villas

    Holiday Rental in Downtown Key West, Key West
    Scored out of 10, guest rating 8.4
    Very good - What previous guests thought, 298 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

  • Key West Villas

    Holiday Rental in Downtown Key West, Key West
    Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 351 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

  • Key West Villas

    Holiday Rental in Downtown Key West, Key West
    Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 351 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

  • Rose Lane Villas

    Holiday Rental in Downtown Key West, Key West
    Scored out of 10, guest rating 8.4
    Very good - What previous guests thought, 298 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