Skip to main content

The best holiday rentals in Florida Keys

Check out our pick of great holiday rentals in Florida Keys

Filter by:


Review score

Superb: 9+ Very good: 8+ Good: 7+ Pleasant: 6+
Our top picks Lowest price first Star rating and price Top reviewed

See the latest prices and deals by choosing your dates.

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. In the center of the town. Everything was very clean. Breakfast was ok.

Show more Show less
9.1
Superb
1,383 reviews
Price from
US$249
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!

Show more Show less
9.3
Superb
1,174 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. Absolutely perfect ! A lovely place in Key West, a real good address. The room is cute, with everything we need. A small terrace just for us (with table and chairs) a beautiful and quiet garden where we have breakfast (really good). The address to keep in mind. Many thanks

Show more Show less
9.1
Superb
1,041 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. Loved the accommodation - great comfortable room out the back. Fabulous location and the Rum Bar was terrific. It was so nice either sitting up to the bar with Kayla mixing the drinks or great people watching sitting out the front with Captain the Cat as company.

Show more Show less
9.1
Superb
381 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. Right at the heart of old town key west.

Show more Show less
9.2
Superb
284 reviews
Price from
US$305
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….

Show more Show less
9
Superb
262 reviews
Price from
US$359
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. The place is just great. Great layout and very nice people.

Show more Show less
9.2
Superb
125 reviews
Price from
US$215
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.

Show more Show less
9.7
Exceptional
321 reviews
Price from
US$349
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. Beautiful and historical. Rooms were stunning and so comfortable with all the amenities. The staff were so friendly and helpful and took the time to show me everything and answer any questions I had. Will definitely be back

Show more Show less
9.4
Superb
206 reviews
Price from
US$313.95
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. 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!

Show more Show less
9
Superb
747 reviews
Price from
US$339
per night

Most booked holiday rentals in Florida Keys this month

FAQs about holiday rentals in Florida Keys

Holiday Rentals that guests love in Florida Keys