Search holiday rentals in Florida Keys

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Featured holiday rental destinations

Destination inspiration for your trip – find a holiday rental

Key West

242 holiday rentals

Key Largo

71 holiday rentals

Marathon

55 holiday rentals

Key Colony Beach

27 holiday rentals

Stock Island

14 holiday rentals

Tavernier

13 holiday rentals

Cudjoe Key

9 holiday rentals

Islamorada

8 holiday rentals

Layton

8 holiday rentals

Duck Key

7 holiday rentals

Big Pine Key

3 holiday rentals

Summerland Key

3 holiday rentals

The best holiday rentals in Florida Keys

Check out our pick of great holiday rentals in Florida Keys

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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.

A
Andrew
From
United Kingdom
Super cute little hotel right in the heart of Duval street, but far enough from the Mallory Square end that it's not totally crazy outside. Tons of great restaurants and bars within a few blocks. Nice little pool and adjoining bar. Our room had a large deck with chairs that faced into some palm trees at the edge of the property. Really nice spot to read in the morning or just chill whenever.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 519 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.

D
Dearbhla
From
Ireland
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!
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 197 reviews
Price from
US$219.45
1 night, 2 adults

Beach House Getaway

Duck Key, Duck Key

Set within the Duck Key district in Duck Key, Beach House Getaway has air conditioning, a patio, and garden views. Both free WiFi and parking on-site are available at the holiday home free of charge.

M
Maggan
From
United Kingdom
Absolute gem of a place, I wish we had booked a longer stay, will definitely be back. The villa is very clean and comfortable and has everything you need. A nice little welcome pack on arrival and very good information booklet before arrival with all necessary details about the area. Ana was fabulous in keeping us up to date and to feel welcome. We did not get a chance to use the kayaks, which is a shame as it was one of the things we were looking forward to. I am not sure how easy it is to actually get them in to the water but I guess if you have some help it is not too hard.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 15 reviews
Price from
US$403.65
1 night, 2 adults

Aquaria House -Pool & Boat Dock

Key West

Boasting air-conditioned accommodation with a private pool, Aquaria House -Pool & Boat Dock is situated in Key West.

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 5 reviews
Price from
US$1,473.15
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$1,572.05
1 night, 2 adults

The Bartlum-Luxurious Studio

Downtown Key West, Key West

In a central area of Key West, located within a short distance of Simonton Street Beach and Key West Aquarium, The Bartlum-Luxurious Studio offers free WiFi, air conditioning and household amenities...

S
SIqintana
From
United States
Offering free parasol/shade umbrella service is great.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 46 reviews
Price from
US$262.89
1 night, 2 adults

Sunrise Suites Saint Lucia Suite #201

Key West

Boasting air-conditioned accommodation with a terrace, Sunrise Suites Saint Lucia Suite #201 is set in Key West. Guests staying at this apartment have access to a balcony.

I
Inge Merete
From
Denmark
The kitchen was super nice and the apartment was clean and cosy
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 11 reviews
Price from
US$389
1 night, 2 adults

Marreros Guest Mansion - Adult Only

Downtown Key West, Key West

Offering a year-round outdoor pool and terrace, this adult-only (21 years +) Marreros Guest Mansion is set in the Duval district in Key West. Duval Street is a 1 minute walk from the property.

R
Robin
From
United States
The location is a big plus. The old charm of the place is great. So much history behind it. The front desk staff (especially Laura) were friendly and helpful with local suggestions.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 71 reviews
Price from
US$309
1 night, 2 adults

Authors Key West Guesthouse

Key West

Featuring free WiFi, a sun terrace with a swimming pool and a garden, Authors Key West Guesthouse is situated in Key West. It is set 1.7 km from South Beach and features a concierge service.

M
Marcelo
From
Brazil
The Room was perfec and comfy. The breakfast was also good. The hotel is in a great location.
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 1,133 reviews
Price from
US$149
1 night, 2 adults

Courtney's Place Historic Cottages & Inns

Downtown Key West, Key West

Offering an outdoor pool, this historic Key West property is just 1 minutes’ walk from Duval Street. Free WiFi and a light continental breakfast are provided daily to all guests.

M
Mateus
From
Brazil
The room we stayed in was unbelivable. Really spacious, with lots of beds. Everything was clean, and the location is good as well, within a 10 minute walk from most of Key West atractions. The office was closed when we arrived, but that wasnt an issue, as the instructions for out check in were left in an envelope. Another plus is the parking spot included. The breakfast is simple but enough to satisfy you.
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 1,276 reviews
Price from
US$249
1 night, 2 adults
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Scored out of 10, guest rating 9.0
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Scored out of 10, guest rating 8.8
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Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 519 reviews

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Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 324 reviews

Popular with guests booking holiday rentals in Florida Keys

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,402 reviews

FAQs about holiday rentals in Florida Keys

Holiday rentals that guests love in Florida Keys

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Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 53 reviews
Location right next to beach and private beach. Layout of villas and the pool and hot tub was really well thought through. Private and quiet.
Guest review by
Pamela
Family with young children
Avg. price/night: US$471.38
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 299 reviews
Everything!!!We loved everything about Rose Lane & especially our Villa Alta. It exceeded our expectations.
Guest review by
Steven
Young couple
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 20 reviews
The villa was well located and well appointed. From beach towels to kitchen appliances, from dishes to kayaks and bikes, this place seemed designed with our comfort and relaxation in mind.
Guest review by
Anne
Young couple
Avg. price/night: US$175.60
Scored out of 10, guest rating 7.4
Good - What previous guests thought, 1,739 reviews
Breakfast was disgusting...Breakfast areas should be for animal that can not fit for human...They are telling us that have breakfast....They have to know what need for breakfast...They dont need to give hotel services...This hotel services look liken village hotel...
Guest review by
Gokhan
Solo traveller
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 292 reviews
Quiet, tucked away in our tree house, like we’re on our own private island- while able to run out and get coffee, and cookies, and gifts, and seashells, and art…within a 5 min walk. Bikes easily accessible on site for venturing to North Duval or Bahama Village.
Guest review by
Johanna
Young couple
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 84 reviews
The property was very well appointed and had the feel of a lovely holiday home rather than a holiday let. There was lots of information to help with the stay- restaurant recommendations, local attraction leaflets. The furnishings were of a lovely quality and created a lovely warm and relaxed ambience
Guest review by
Sarah
Family with young children
Avg. price/night: US$246.38
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 333 reviews
Excellent location and villa setup. We loved the porch.
Guest review by
Olga
Family with young children
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 7 reviews
Unit was beautiful. 3 stories, comfortable. No complaints about the owners unit. It was good and he is a conscientious owner. Great beds. Overall the villa property was nice.
Guest review by
James
Solo traveller
Avg. price/night: US$163.13
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 944 reviews
Fresh baked muffins, individual frittatas, yogurt, fruit, coffee all served outdoors under a tiki hut with tables and chairs by your villa all a short walk from the shore with a great view. It's an old school Florida hotel. Refreshing break from the standard modern hotels.
Guest review by
Bethel
Family with young children
Avg. price/night: US$667.46
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 129 reviews
very nice views of the Marina, but there are also large dry dock barns behind the villas They are nicely furnished, but not enough comfortable seating for 4 adults The beds were very comfortable!
Guest review by
Evans
People with friends
gogless