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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. The room, the staff, the breakfast … all !! Beautiful moment !!

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9.2
Superb
1,384 reviews
Price from
US$259
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. Beautiful historic property in perfect location. Rooms were well appointed and very clean. Staff were friendly and helpful. A wonderful place to stay.

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9.3
Superb
1,175 reviews
Price from
US$378.35
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. I did self checkin, it was super easy due to perfect instructions from the team. Everyone was so polite and nice! I like it! The breakfast was great! I recommend!

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9.1
Superb
1,040 reviews
Price from
US$349
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
Superb
380 reviews
Price from
US$349.67
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. Fantastic location, oasis in the city

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9.2
Superb
291 reviews
Price from
US$355
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. the history, the location, and the staff was amazing….

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9
Superb
263 reviews
Price from
US$419
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. So close to the water and very personal staff, other quests were friendly like a family atmosphere

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9.2
Superb
122 reviews
Price from
US$295
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. If I could give more than 10 I would! Everything was perfect: the location (in the heart of Key West, parking space available), the rooms (they’re even nicer as on the homepage), the poolside.. everything was so tasteful and clean. And of course the hosts ! They make everything to make you feel home. Snacks and drinks available all day long, happy hour every day and the bottle of wine offered upon arrival!! We just can strongly recommend this lovely place.

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9.7
Exceptional
322 reviews
Price from
US$379
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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9.4
Superb
206 reviews
Price from
US$292.95
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
747 reviews
Price from
US$339
per night

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