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

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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
Jeffrey
From
United States
The Concierge (Foster) who checked us in, out and everything in between was truly exceptional. We felt at home thanks to Foster. The rest of the staff were also very friendly and always smiling. The room's television was larger than most hotels and is a perfect fit for the room. We shared a deck, under the trees, with our neighboring room. Our doorway onto the deck was our only doorway and was a French door. This was a nice touch for a romantic birthday get-a-way. The room was very nice and the mattress and pillows were extremely comfortable.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,418 reviews
Price from
US$219
1 night, 2 adults
Check availability

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.

F
Francesca
From
Switzerland
We had a lovely time in this romantic guesthouse as a 30 y.o. couple. The room was quite big and clean, bathroom was spacious and the balcony was so nice. We were on the first floor, and there was armchairs to sit in outside there and just enjoy the ocean breeze. Magical. The bar was quite cool as well, with live music. A pity that they stop playing at 19:00 and close the bar at 19:30 though. Breakfast was a lot of options, homemade cooking kinda vibe, we enjoyed it a lot. Parking was very convenient, I don’t understand the bad reviews about the distance. Guys, it’s literally 1 minutes walk. It’s good for you, just walk. It’s not gonna kill you. Strongly recommend!
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,173 reviews
Price from
US$481.85
1 night, 2 adults
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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.

T
Theodore
From
Greece
one of the most authentic and best places we’ve ever slept. really an amazing experience. breakfast was awesome as well.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,057 reviews
Price from
US$289
1 night, 2 adults
Check availability

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, 526 reviews
Price from
US$145
1 night, 2 adults
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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
Check availability

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$1,384.60
1 night, 2 adults
Check availability

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$828
1 night, 2 adults
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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
Check availability

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.

S
Stephen
From
United Kingdom
It is very spacious and well laid out.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 33 reviews
Price from
US$288.65
1 night, 2 adults
Check availability

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
Check availability
All holiday rentals in Key West

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

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Highly rated holiday rentals in Key West and nearby

  • Scored out of 10, guest rating 8.1
    Very good - What previous guests thought, 471 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 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$906.41 per night
  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 5 reviews

    Situated in the centre of Key West, 700 metres from South Beach and 300 metres from Duval Street, Duval Street Suite overlooking Duval with parking and pool offers free WiFi, a garden and air...

  • 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$201.38 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, 1,274 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$325.13 per night
  • Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 406 reviews

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

    From US$275.29 per night

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

  • Scored out of 10, guest rating 7.4
    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...

    From US$1,220.40 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$962.04 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$1,310.23 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$524.48 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

  • Sky Loft in Key West

    Downtown Key West, Key West
    Free cancellation options available
    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$502.54 per night

  • 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$850.82 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$829.86 per night

Enjoy breakfast in Key West and nearby

  • 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$493.88 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 8.7
    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.

    From US$257.63 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$310.50 per night
  • Scored out of 10, guest rating 7.4
    Good - What previous guests thought, 1,787 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$165.48 per night
  • Scored out of 10, guest rating 8.7
    Fabulous - What previous guests thought, 754 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$236.25 per night
  • Scored out of 10, guest rating 8.7
    Fabulous - What previous guests thought, 1,165 reviews

    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.

    From US$156.38 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.

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
    Avg. price/night: US$336.38
    Scored out of 10, guest rating 8.5
    Very good - What previous guests thought, 300 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
    Avg. price/night: US$426.38
    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

  • Key West Villas

    Holiday Rental in Downtown Key West, Key West
    Avg. price/night: US$426.38
    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

  • Rose Lane Villas

    Holiday Rental in Downtown Key West, Key West
    Avg. price/night: US$336.38
    Scored out of 10, guest rating 8.5
    Very good - What previous guests thought, 300 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