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The best holiday rentals in Florida Keys

Check out our pick of great holiday rentals in Florida Keys

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Superb: 9+ Very good: 8+ Good: 7+ Pleasant: 6+
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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 a terrace. Breakfast, comfortable bed, clean room/area!

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9
Superb
1,417 reviews
Price from
US$99
per night

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. Features include a free hot American breakfast and a hot tub.The property is located across 4 buildings. 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!

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9.2
Superb
1,169 reviews
Price from
US$182.85
per night

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. Guests will enjoy a daily breakfast including pastries, organic fruit, and dessert cakes during their stay. We had a great stay at Old Town Manor - friendly staff, delicious breakfast, large room. Will definitely stay here again once we will be back in Key West.

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9.1
Superb
1,057 reviews
Price from
US$124
per night

Offering a bar and garden view, The Speakeasy Inn and Rum Bar is situated in Key West, 500 metres from Southernmost Point and 400 metres from Ernest Hemingway Home and Museum. This bed and breakfast features free private parking and luggage storage space. The property is 400 metres from the city centre and 400 metres from South Beach. It was very well equipped with all the things you need to make your stay enjoyable & then some. It had a whole range of coffee flavours, face cloths, make up wipes, complimentary pain killer drinks, umbrella, towels &, free parking. It was perfectly situated within duval strret; quiet yet still part of the atmosphere. Beds were extremely comfortable!

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9.1
Superb
353 reviews
Price from
US$130
per night

Situated in the centre of Key West, 600 metres from Simonton Street Beach, the historic Key West Harbor Inn - Adults Only features accommodation with free WiFi and an indoor pool. The property has pool and garden views, and is 600 metres from Key West Aquarium. The bed and breakfast also offers facilities for disabled guests. It was a quaint little tropical paradise! The grounds are beautiful. The room was spacious, comfortable, and clean!

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9.2
Superb
321 reviews
Price from
US$245
per night

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 terrace. Location location this was great you were a block maybe two away from Sloppy Joe's and Deval Street close to Mallory Square you are off the beaten path but close to everything I would recommend this it was wonderful I felt safe staying there after hours they lock the gate so you had a key to get in but I could walk back to my room feeling safe it was a wonderful place to stay the staff was wonderful this will be my new place every time I come to the Keys now which is once a year

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9
Superb
261 reviews
Price from
US$169
per night

All rooms feature a private bath, small refrigerator, and microwave. Apartments at Key West Villas include a fully-equipped kitchen and seating area.

Key West Villas guests can hire a bicycle and explore Key West. A guest launderette is available as well. We went there for two nights. The location was amazing. The service is awesome. A truly quiet pool area, good breakfast with all you need, and the happy hour with cocktails for free. We definitely will come back!!

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9.7
Exceptional
372 reviews
Price from
US$399
per night

This historical Key West bed and breakfast is 1 mile from the Southernmost Point and 3 minute’s walk from iconic Duval Street. The Artist House guests will enjoy a daily continental breakfast and spa hot tub. One word - WOW!! Absolutely loved our stay here and will be back! The rooms are massive for Key West with charming decor. Staff are incredible, so friendly and helpful. Fantastic complementary breakfast in the gorgeous garden. Can’t recommend this place highly enough!

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9.5
Exceptional
165 reviews
Price from
US$118.65
per night

This Key West bed and breakfast is 3 minutes’ walk from the art galleries and cafés of historic Duval Street. Guests can start their day with a full hot breakfast and enjoy two outdoor pools.

All accommodations feature a small refrigerator and microwave. Ambrosia Key West guests will also have in-suite Keurig® tea- and coffee-making facilities. Location was great. The room fabulous. It would be nice if a mirror could be added. Beautiful garden terrace. Nice spa in the garden. Very friendly and helpful staff.

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9
Superb
779 reviews
Price from
US$179
per night

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.

A flat-screen TV and an iPod docking station are featured in each classic room at this Key West bed and breakfast. Guests will also enjoy the convenience of a refrigerator in their room. Rooms also have a clock radio with auxiliary cables. Izabella at the reception was super helpful and friendly. The location and the room were perfect and the breakfast was delicious. We will definitely come back again.

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9.5
Exceptional
147 reviews
Price from
US$232.47
per night

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