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Holiday Rentals in Key West

Find the holiday rentals that appeal to you the most

The best holiday rentals in Key West

Check out our pick of great holiday rentals in Key West

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L'Habitation Guesthouse- Adult Exclusive

Downtown Key West, Key West

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...

t
tracey
From
United Kingdom
fabulous location in the middle of everything. but stil quiet . our room was big comfy and spotless. the maids were superb every day. staff si friendly
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,422 reviews
Price from
US$219
1 night, 2 adults

Southernmost Point Guest House & Garden Bar

Downtown Key West, Key West

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.

J
Janno
From
Estonia
Supreme location if you travel with kids and prefer a less noisy area of the main street. It was dead quiet during nighttime. It is at the end (or beginning) of Duval street and yet it is well close enough to all the Key West action. Staff was extraordinarily helpful and rooms were very nice. Very easy parking just next to the rooms. Breakfast was good and we liked the setup where you get your coffee and food and then just take it outside to enjoy your breakfast with a nice morning breeze from ocean which is just 100 meters away. I think the whole concept of this establishment gives you a really nice understanding of "Key West" way of living. Really good :)
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,176 reviews
Price from
US$481.85
1 night, 2 adults

Old Town Manor

Downtown Key West, Key West

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.

A
Ante
From
Spain
Room was extremey clean and comfortable
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,059 reviews
Price from
US$289
1 night, 2 adults

Grand Marina Suite -Waterfront Condo

Key West

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.

K
Kim
From
United States
Large room for a family, has everything you need. Lovely place with a wonderful pool with a beautiful view.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 124 reviews
Price from
US$422.28
1 night, 2 adults

Weatherstation Inn Circa 1911

Downtown Key West, Key West

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...

B
BURAK
From
Turkey
The location is fantastic! In a quiet and secure neighborhood, surrounded by trees and adjacent to the ocean. We wished if we stayed more.
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 258 reviews
Price from
US$199
1 night, 2 adults

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.

W
William
From
United States
Amazing hotel. Met all my expectations.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 523 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.

K
Kaicheng
From
United States
Great breakfast, beautiful room decor, perfect location
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 187 reviews
Price from
US$219.45
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$918.85
1 night, 2 adults

Keys Please!

Downtown Key West, Key West

Set in the centre of Key West, 300 metres from South Beach and 400 metres from Southernmost Point, Keys Please! offers free WiFi, a garden and air conditioning.

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 6 reviews
Price from
US$762.45
1 night, 2 adults

The St Martin -Hot Tub & Pool

Key West

Boasting air-conditioned accommodation with a patio, The St Martin -Hot Tub & Pool is situated in Key West. Both free WiFi and parking on-site are accessible at the holiday home free of charge.

g
gary
From
United Kingdom
Tennis court nearby and decent pool
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 16 reviews
Price from
US$264.50
1 night, 2 adults
All holiday rentals in Key West

Most booked holiday rentals in Key West and surroundings in the past month

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Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 659 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 815 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,059 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 1,161 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 523 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 312 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,418 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 865 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 7.4
Good - What previous guests thought, 1,767 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,179 reviews

Holiday Rentals with swimming pools in Key West and nearby

Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 17 reviews

Located within the Downtown Key West district in Key West, Road's End has air conditioning, a patio, and city views.

Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 14 reviews

Located in the centre of Key West, 600 metres from South Beach and 500 metres from Ernest Hemingway Home and Museum, New Casa Caribe by Brightwild- Two-Story Condo Rooftop Pool offers free WiFi and...

From US$1,055.19 per night
Scored out of 10, guest rating 5.0
Passable - What previous guests thought, 2 reviews

Set in the centre of Key West, 600 metres from South Beach and 500 metres from Ernest Hemingway Home and Museum, NEW!

From US$1,134.11 per night
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Set in Key West, 300 metres from Duval Street and 200 metres from Ernest Hemingway Home and Museum, Duval Street Suite w kitchen and shared heated pool offers a garden and air conditioning.

From US$250.58 per night
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 815 reviews

Located centrally on lively Duval Street, Duval House offers a continental breakfast that includes Belgian waffles. The 7 Caribbean-style buildings offer free WiFi.

From US$325.13 per night
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 189 reviews

Located above a nightclub on historic Duval Street in Key West, Florida, this gay male guest house features an outdoor swimming pool, a clothing-optional sundeck, and an on-site restaurant.

From US$248.92 per night
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 30 reviews

This adult-only Conch House Heritage Inn offers accommodation in Key West with breakfast included and complimentary mimosas.

From US$429.30 per night
Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 14 reviews

Key Lime Calypso is set in the Downtown Key West district of Key West, 200 metres from Ernest Hemingway Home and Museum, 200 metres from Duval Street and less than 1 km from Southernmost Point.

These holiday rentals in Key West and nearby have options with free cancellation

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 26 reviews

In the heart of Key West, set within a short distance of South Beach and Ernest Hemingway Home and Museum, Sea Breeze -Great Location!

From US$798.81 per night

Sky Suite On Duval

Downtown Key West, Key West
Free cancellation options available
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 8 reviews

Set in the centre of Key West, less than 1 km from South Beach and a 1-minute walk from Duval Street, Sky Suite On Duval offers free WiFi and air conditioning.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Located in the centre of Key West, less than 1 km from South Beach and a 3-minute walk from Duval Street, Contra House -Luxury Home With Pool offers free WiFi, a garden and air conditioning.

From US$1,798.71 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 659 reviews

Set in Key West, less than 1 km from South Beach, La Pensione Inn - Adult Exclusive offers accommodation with an outdoor swimming pool, free private parking, a shared lounge and a terrace.

From US$291.38 per night

Sky Loft in Key West

Downtown Key West, Key West
Free cancellation options available
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 15 reviews

In the centre of Key West, located within a short distance of Simonton Street Beach and Duval Street, Sky Loft in Key West offers free WiFi, air conditioning and household amenities such as a...

From US$616.39 per night

The Collins on Duval

Downtown Key West, Key West
Free cancellation options available
Scored out of 10, guest rating 6.4
Pleasant - What previous guests thought, 6 reviews

In the heart of Key West, set within a short distance of Simonton Street Beach and Duval Street, The Collins on Duval offers free WiFi, air conditioning and household amenities such as a fridge and...

From US$1,026.63 per night

Duval Dream Loft on Duval

Downtown Key West, Key West
Free cancellation options available
Scored out of 10, guest rating 7.1
Good - What previous guests thought, 27 reviews

Situated in the centre of Key West, less than 1 km from Simonton Street Beach and a 3-minute walk from Duval Street, Duval Dream Loft on Duval offers free WiFi and air conditioning.

From US$964.92 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 865 reviews

Alexander Palms Court - No Hidden Resort Fees! provides accommodation located less than 1 km from the centre of Key West and features an outdoor swimming pool and a garden.

From US$403.88 per night

Enjoy breakfast in Key West and nearby

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 1,273 reviews

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.

From US$325.13 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 403 reviews

Featuring free WiFi throughout this adult-only property, Caribbean House offers accommodation in Key West.

From US$363.04 per night
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 859 reviews

This all-adult bed and breakfast is within a 10-minute walk of Duval Street and the Atlantic Ocean.

From US$477.97 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 312 reviews

Key West Bed and Breakfast, a property with a garden, is situated in Key West, 1.2 km from Key West Aquarium, 1.3 km from Ernest Hemingway Home and Museum, as well as 1.1 km from Mallory Dock.

From US$201.38 per night
Scored out of 10, guest rating 7.4
Good - What previous guests thought, 1,767 reviews

This bed and breakfast welcomes guests to Old Town, Key West and boasts a free continental breakfast, 3 outdoor pools and a hot tub. The Ernest Hemingway Home and Museum is 15 minutes’ walk away.

From US$236.35 per night
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 738 reviews

Within walking distance of the beach, local attractions and activities, this Old Town Key West inn features on-site laundry facilities, comfortable guest rooms and an extended continental breakfast.

From US$258.75 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 1,161 reviews

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.

From US$280.13 per night

Paradise Suite has a patio and is situated in Key West, within just 400 metres of Duval Street and 300 metres of Ernest Hemingway Home and Museum.

Highly rated holiday rentals in Key West and nearby

Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 472 reviews

Located in Key West, Florida, these furnished self-catering apartments feature free WiFi access. The Ernest Hemingway Home and Museum is only 3 minutes’ walk away from Old Town Suites.

From US$430.05 per night
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 301 reviews

Located in Key West, Florida, these villas feature a heated outdoor swimming pool. They are adjacent to dining and shopping on Duval Street. and 1.8 km from the Southernmost Point.

From US$358.88 per night
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 46 reviews

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...

From US$472.31 per night
Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 11 reviews

Right in the heart of Key West, situated within a short distance of Simonton Street Beach and Key West Aquarium, Mesa House, Dos -Unreal Location offers free WiFi, air conditioning and household...

From US$950.57 per night
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 9 reviews

Attractively situated in Key West, Classic King Balcony at the James House features air-conditioned rooms, a garden and free WiFi.

From US$342.86 per night
Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 39 reviews

Ideally set in the centre of Key West, King Suite at Curry Mansion with Heated Pool! features free WiFi throughout the property and a garden.

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 21 reviews

Located in Key West in the Florida region, Sunrise Suites Big Kahuna Suite #202 has a balcony. Guests can benefit from a terrace and an outdoor pool. The apartment features a hot tub and a lift.

From US$694.74 per night
Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 51 reviews

Set in Key West, 6.5 km from Southernmost Point and 7.3 km from Ernest Hemingway Home and Museum, The Barbados -Bright Condo w Pool offers air conditioning.

From US$656.78 per night

FAQ about holiday rentals in Key West

Holiday rentals that guests love in Key West

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Avg. price/night: US$358.88
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 301 reviews
best location!! plenty of space for the family!! i will surely come back and stay the villas!!
Guest review by
Ailen
Family with young children
Avg. price/night: US$471.38
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 343 reviews
Everything was wonderful. The villas had everything you needed to make your trip enjoyable. Looking forward to going back again soon.
Guest review by
erica
Group
Avg. price/night: US$471.38
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 343 reviews
Perfect location, but even more importantly, Heather and Kevin were dream hosts. The snacks, cocktails and customer service were outstanding. I would recommend Key West villas to everyone!
Guest review by
Thomas
Group
Avg. price/night: US$358.88
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 301 reviews
Absolutely beautiful great sized villa. Comfortable, convenient location, staff was excellent and villa was spotless. Parking and pet friendly with a nice pool - all excellent bonuses! So nice that when I walked in I immediately called the office and extended my stay by two nights!
Guest review by
lisa
Solo traveller