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. Breakfast, comfortable bed, clean room/area!

Show more Show less
9.1
Superb
1,413 reviews
Price from
US$109
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. Absolutely everything! We booked room 6 and we're not disappointed as it was excellent. The whole house,location and staff on site were first class ... 5 star. It is my new favourite place .

Show more Show less
9.3
Superb
1,185 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. Wonderful garden, room in typical style, perfect site, near center,

Show more Show less
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. 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!

Show more Show less
9
Superb
368 reviews
Price from
US$241.67
per night

Located in Key West, 9.1 km from Ernest Hemingway Home and Museum and 9.2 km from Duval Street, Grand Marina Suite -Waterfront Condo offers a garden and air conditioning. The property is set 10 km from Southernmost Point, 10 km from Key West Aquarium and 10 km from Mallory Dock. Providing free WiFi throughout the property, the non-smoking holiday home has a fitness centre. We were in a different place. It was not conducive for me as I have difficulty walking. The staff was efficient, professional, great communicators, and attentive.

Show more Show less
9
Superb
126 reviews
Price from
US$310.50
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.

Show more Show less
9.2
Superb
304 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. Quiet location, gated community. Close to Mallory Square en Duval. Spacious rooms, excellent beds.

Show more Show less
9
Superb
258 reviews
Price from
US$169
per night

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 flat-screen TV with cable channels is provided in each spacious room at The Casablanca Hotel. A private bathroom is also provided in every air-conditioned guest room. Offer oatmeal, cereal, or some sort for breakfast.

Show more Show less
9
Superb
523 reviews
Price from
US$100
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
9.1
Superb
119 reviews
Price from
US$185
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
340 reviews
Price from
US$279
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

gogless