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

S
Sue
From
Australia
Our host Foster was fantastic. We were welcomed with a smile and made to feel at home. Facilities were good and breakfast was plentiful. The bed was very comfortable. The complex was very close so everything. Just metres away from Duval Street. Thank you for a nice stay. We recommend L' Habitaion Guest house and would loved to have stayed longer.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,418 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.

T
Thomas Tan
From
Singapore
Great location, spacious room, free parking and daily drinks included.
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,174 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.

A
Ashanahan9
From
Canada
What a hidden gem! Clean and cozy. Air-conditioned. Amazing breakfast. Right in the heart of Key West. Recommended!
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,059 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.

S
Steve
From
Canada
The staff was very friendly and the room was very clean. The location was great as well. The bedding felt luxurious, and was a comfy sleep.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 527 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.

B
Ben9Copenhagen
From
Denmark
AMAZING! WOW - this place was so nice and the staff was so kind and friendly. We had the most beautiful room with fridge, coffee & tea. A very nice breakfast and snacks available in the kitchen. A nice and cozy court yard with spa.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 184 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$1,361.60
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$829.15
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$244.95
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
Natalia
From
Canada
It was simply amazing! Dream come true! Super location, clean, slick, comfortable, beach, swimming pool, very helpful personnel - highly recommend
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 33 reviews
Price from
US$288.65
1 night, 2 adults

Sky Loft in Key West

Downtown Key West, Key West

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...

P
Patrick
From
United Kingdom
Location, and general layout of the property.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 16 reviews
Price from
US$347.30
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 7.5
    Good - What previous guests thought, 17 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$1,216.52 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$903.83 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$958.16 per night
  • Scored out of 10, guest rating 8.6
    Fabulous - What previous guests thought, 25 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$638.38 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$1,305.06 per night
  • 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, 46 reviews

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

    From US$521.89 per night
  • Scored out of 10, guest rating 10.0
    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 casino and air conditioning.

    From US$1,798.71 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$212.63 per night

Enjoy breakfast in Key West and nearby

  • Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 819 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$156.38 per night
  • 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.

    From US$410.13 per night
  • 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.

    From US$334.80 per night
  • 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, 405 reviews

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

    From US$275.29 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.

    From US$415.13 per night
  • 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.

    From US$396.84 per night
  • Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 310 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$257.63 per night

Highly rated holiday rentals in Key West and nearby

  • Scored out of 10, guest rating 8.1
    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$258.48 per night
  • 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...

    From US$499.95 per night
  • Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 868 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$415.13 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$336.38 per night
  • Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 356 reviews

    Well located in Key West, The Garden House provides express check-in and check-out and private parking.

    From US$263.25 per night
  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 47 reviews

    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...

  • Scored out of 10, guest rating 8.0
    Very good - What previous guests thought, 23 reviews

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

    From US$423.62 per night
  • Scored out of 10, guest rating 8.2
    Very good - What previous guests thought, 11 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$795.32 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$336.38
    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$392.63
    Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 350 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$392.63
    Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 350 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$336.38
    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