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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. Good location Great staff at the reception Good breakfast

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9.1
Superb
1,413 reviews
Price from
US$89
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. Very clean, friendly staff - especially Maxwell at the bar, Sandy’s food truck and staff, great location, breakfast included in always nice as well.

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9.2
Superb
1,164 reviews
Price from
US$136.85
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. Room was extremey clean and comfortable

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9.1
Superb
1,053 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. A picturesque and cozy hotel with an excellent location

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9.1
Superb
356 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. Great location, close to all the action yet quiet. Amazing, friendly stuff.

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9.2
Superb
317 reviews
Price from
US$230
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
259 reviews
Price from
US$159
per night

Featuring garden views, Coconut Bay Resort - Key Largo provides accommodation with water sports facilities, pool with a view and a garden, around 5.1 km from Pigeon Key. With a private beach area, the 3-star aparthotel has air-conditioned rooms with free WiFi, each with a private bathroom. The aparthotel features family rooms as well as facilities for disabled guests. Everything! The grounds are well kept. The cottages are very clean. Kayaks and other water equipment are well maintained and clean. The fresh scones and coffee in the morning are a bonus. We will definitely stay here again!!

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9
Superb
116 reviews
Price from
US$165
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. This place is exceptional, very clean, cozy and centrally located- just perfect for our stay in Key West. The hosts warmly welcomed us and were extremely friendly and helpful throughout our stay. On top of anything else we very much appreciated the availability of comfortable pool towels, a really good washing machine & dryer and much more little things that were even complimentary to our surprise. The pool and hot tub are very nice too and are open until 10pm. We can highly recommend this facility and will definitely return when coming back to Key West.

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9.7
Exceptional
363 reviews
Price from
US$289
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. The place is INCREDIBLE! Charming, beautiful, interesting, fun and so much more. I have been to Key West dozens of times and this is the best place I stayed by far, I would take it over any fancy hotel I have stayed in the area. Sophia and Shawn (or Sean?) are perfect hosts. The breakfast is great, with fruit, mimosas, great coffee and much more. They also hace a charming Happy Hour that they serve cheese and crackers and good wine.

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9.5
Exceptional
171 reviews
Price from
US$131.25
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. My husband and I stayed 2 nights in the poolside room #110 (second floor). It was wonderful and included coffee, tea, a refrigerator, a couple of chairs on the patio and robes. We found street parking for free on William street a couple blocks away. I’m glad we picked the basic poolside room because it was lovely and up to date. Would definitely recommend!

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9
Superb
780 reviews
Price from
US$189
per night

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