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
Shelly
From
Israel
Beautiful house, great hosts, very clean room and a comfy bed. Close to the nain street yet quiet. Delicious breakfast.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,419 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.

E
Elaine
From
Falkland Islands (Malvinas)
The room was spectacular and breakfast was delicious
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,177 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.

M
Marcin
From
Poland
Climate place :) Great breakfast in the garden :)
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,055 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, 526 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, 185 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$1,357
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$815.35
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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Holiday Rentals with swimming pools in Key West and nearby

  • 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$2,025.11 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$1,537.76 per night
  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    Set in Key West, 300 metres from Duval Street and 200 metres from Ernest Hemingway Home and Museum, Duval Street Suite w kitchen and shared heated pool offers a garden and air conditioning.

  • 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 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$753.19 per night
  • 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$646.99 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$656.04 per night
  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 4 reviews

    Located in the centre of Key West, 700 metres from Higgs Beach and 1 km from Southernmost Point, Sunnyside Up offers free WiFi, a garden and air conditioning.

    From US$1,480.89 per night

Enjoy breakfast in Key West and nearby

  • Scored out of 10, guest rating 8.6
    Fabulous - What previous guests thought, 864 reviews

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

    From US$404.22 per night
  • Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 311 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$258.75 per night
  • Scored out of 10, guest rating 7.4
    Good - What previous guests thought, 1,779 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$388.23 per night
  • Scored out of 10, guest rating 8.7
    Fabulous - What previous guests thought, 752 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$388.13 per night
  • Scored out of 10, guest rating 8.1
    Very good - What previous guests thought, 470 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$677.25 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, 26 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...

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

  • 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, 45 reviews

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

    From US$872.49 per night
  • Creme Brulee Suite

    Downtown Key West, Key West
    Free cancellation options available
    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$741.88 per night
  • Banana Split

    Downtown Key West, Key West
    Free cancellation options available
    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$1,049.85 per night
  • Sugar Pie Suite

    Downtown Key West, Key West
    Free cancellation options available
    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$709.54 per night
  • Sweet Caroline

    Downtown Key West, Key West
    Free cancellation options available
    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$1,681.09 per night
  • Key Lime Cottage

    Downtown Key West, Key West
    Free cancellation options available
    Scored out of 10, guest rating 4.0
    Disappointing - What previous guests thought, 1 review

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

    From US$797.51 per night
  • Honey Bun Hideaway

    Downtown Key West, Key West
    Free cancellation options available
    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$551.70 per night
  • Scored out of 10, guest rating 8.5
    Very good - What previous guests thought, 8 reviews

    Attractively situated in Key West, Classic King Balcony at the James House features air-conditioned rooms, a garden and free WiFi.

    From US$510.12 per night

Highly rated holiday rentals in Key West and nearby

  • Scored out of 10, guest rating 8.0
    Very good - What previous guests thought, 50 reviews

    Set in Key West, 6.5 km from Southernmost Point and 7.3 km from Ernest Hemingway Home and Museum, The Barbados -Bright Condo w Pool offers air conditioning.

    From US$805.56 per night
  • Scored out of 10, guest rating 8.3
    Very good - What previous guests thought, 49 reviews

    Tortuga Suite at Sunrise Suites Resort - Heated Pool, Hot Tub & Free Parking is set in Key West, 6.5 km from Southernmost Point, 7.3 km from Ernest Hemingway Home and Museum, and 7.4 km from Duval...

    From US$821.08 per night
  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 526 reviews

    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.

    From US$309.38 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$1,070.49 per night
  • Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 150 reviews

    Located right off Duval Street, the Andrews Inn and Garden Cottages are less than 5 minutes’ walk from various dining and entertainment options. Guests can enjoy free WiFi and an outdoor pool.

  • Scored out of 10, guest rating 8.2
    Very good - What previous guests thought, 8 reviews

    Featuring air-conditioned accommodation with a balcony, Crawl to Duval w/ Hot tub is located in Key West. This property offers access to a terrace and free private parking.

  • 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$1,611.51 per night
  • Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 6 reviews

    In a central area of Key West, located within a short distance of South Beach and Duval Street, Poolside Suite offers free WiFi, air conditioning and household amenities such as an oven and kettle.

    From US$898.71 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$618.75
    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$370.13
    Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 349 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$370.13
    Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 349 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$618.75
    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