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Vacation Rentals in Key West

Find the vacation rentals that appeal to you the most

The best vacation rentals in Key West

Check out our selection of great vacation rentals in Key West

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L'Habitation Guesthouse- Adult Exclusive

Downtown Key West, Key West

Located in Key West, 1969 feet from Key West Aquarium and 1969 feet from Mallory Dock, L'Habitation Guest house- Adult Exclusive provides accommodations with free WiFi, air conditioning, a garden and...

L
Lucian
From
Romania
Excellent location,in the heart of the old town!
Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 1,422 reviews
Price from
$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 361 feet from the Southernmost Point and 240 feet from the beach.

M
Markus
From
Germany
Unique, indescribable! It was a unique, positively surprising stay in this house furnished with excellent taste and finesse.
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 1,176 reviews
Price from
$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 mi from the Southernmost Point.

E
Eduard
From
Moldova
We had a great stay at Old Town Manor - friendly staff, delicious breakfast, large room. Will definitely stay here again once we will be back in Key West.
Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 1,059 reviews
Price from
$289
1 night, 2 adults

Grand Marina Suite -Waterfront Condo

Key West

5.7 miles from Ernest Hemingway Home and Museum in Key West, Grand Marina Suite -Waterfront Condo provides accommodations with access to a fitness center.

L
LaVerna
From
United States
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.
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 124 reviews
Price from
$422.28
1 night, 2 adults

Weatherstation Inn Circa 1911

Downtown Key West, Key West

Set within 1640 feet 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...

W
Wendy
From
United States
it’s a beautiful place, very clean and comfortable. The staff was great and very responsive. We asked for an extra blanket while down at breakfast and it was delivered to our room in minutes. There were plenty of options for breakfast including pastries from a local restaurant.
Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 258 reviews
Price from
$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.

L
LAURO
From
Brazil
Beautiful, renewed, organized and clean, filled with courtesy and kindness, in a great location downtown, really close to the beach…
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 523 reviews
Price from
$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.

C
Chrys
From
Brazil
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.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 187 reviews
Price from
$219.45
1 night, 2 adults

Evershore House -Pool, Parking, Dock!

Key West

Evershore House -Pool, Parking, Dock! is located in Key West, just 5.3 miles from Ernest Hemingway Home and Museum and 5.3 miles from Duval Street.

J
Jonathan
From
United States
Spacious , comfortable, amenities were great, close to key west!
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 5 reviews
Price from
$918.85
1 night, 2 adults

Keys Please!

Downtown Key West, Key West

Keys Please! is located in Key West, just 1.1 miles from Key West Aquarium and 1.1 miles from Mallory Dock. This vacation home offers air-conditioned accommodations with free Wifi.

O
Olena
From
United States
Paradise. Thank you, everything was perfect.
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 6 reviews
Price from
$770.50
1 night, 2 adults

The St Martin -Hot Tub & Pool

Key West

The St Martin -Hot Tub & Pool offers accommodations in Key West, 4 miles from Southernmost Point and 4.6 miles from Ernest Hemingway Home and Museum.

C
Christina
From
United States
The place was clean and comfortable. The location was perfect...close to all the action but far enough no traffic or noise from the busy areas in town. The pool and spa were very well maintained.
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 16 reviews
Price from
$269.10
1 night, 2 adults
All vacation rentals in Key West

Most booked vacation rentals in Key West and surrounding area in the past month

See all

Popular with guests booking vacation rentals in Key West

Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 813 reviews

Popular with guests booking vacation rentals in Key West

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

Popular with guests booking vacation rentals in Key West

Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 1,057 reviews

Popular with guests booking vacation rentals in Key West

Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 1,160 reviews

Popular with guests booking vacation rentals in Key West

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 522 reviews

Popular with guests booking vacation rentals in Key West

Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 313 reviews

Popular with guests booking vacation rentals in Key West

Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 862 reviews

Popular with guests booking vacation rentals in Key West

Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 1,417 reviews

Popular with guests booking vacation rentals in Key West

Scored out of 10, guest rating 7.4
Good - What previous guests thought, 1,765 reviews

Popular with guests booking vacation rentals in Key West

Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 1,182 reviews

Enjoy breakfast in Key West and nearby

Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 813 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 $325.13 per night
Scored out of 10, guest rating 8.9
Excellent - 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 $248.92 per night
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 31 reviews

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

From $429.30 per night
Scored out of 10, guest rating 8.8
Excellent - 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 $325.13 per night
Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 403 reviews

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

From $363.04 per night
Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 659 reviews

Located in Key West, a 11-minute walk from South Beach, La Pensione Inn - Adult Exclusive provides accommodations with an outdoor swimming pool, free private parking, a shared lounge and a terrace.

From $291.38 per night
Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 859 reviews

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

From $477.97 per night
Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 313 reviews

Key West Bed and Breakfast features rooms with free Wifi in the center of Key West. Featuring a garden, the property is located within a 13-minute walk of Simonton Street Beach.

From $201.38 per night

Highly rated vacation 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 $430.05 per night
Scored out of 10, guest rating 8.5
Very Good - What previous guests thought, 17 reviews

Road's End offers accommodations in Key West, a 16-minute walk from Key West Aquarium and 0.9 miles from Mallory Dock. This apartment features air-conditioned accommodations with a patio.

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

Sea Breeze -Great Location! is located in Key West, just a 16-minute walk from Key West Aquarium and 0.9 miles from Mallory Dock.

From $801.39 per night
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 15 reviews

Sky Loft in Key West offers accommodations in Key West, a 13-minute walk from Mallory Dock and 0.7 miles from Mallory Square. This vacation home provides accommodations with a patio and free Wifi.

From $616.39 per night
Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 862 reviews

Alexander Palms Court - No Hidden Resort Fees! is a guest house featuring rooms with free Wifi and air conditioning in the center of Key West.

From $403.88 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 1.1 mi from the Southernmost Point.

From $358.88 per night
Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 353 reviews

The Garden House provides rooms in Key West near Mallory Square and Ernest Hemingway Home and Museum.

From $277.88 per night
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 46 reviews

The Bartlum-Luxurious Studio is located in Key West, just a 8-minute walk from Duval Street and 0.7 miles from Ernest Hemingway Home and Museum.

From $474.64 per night

Vacation Rentals with swimming pools in Key West and nearby

Scored out of 10, guest rating 7.5
Good - What previous guests thought, 17 reviews

Casa Key West-Pool & Free Parking offers accommodations in Key West, a 19-minute walk from Key West Aquarium and one mile from Mallory Dock.

From $1,483.03 per night
Scored out of 10, guest rating 5.0
Fair - What previous guests thought, 2 reviews

NEW! Villa Positano - Duval Square Condo, Pool, Hot Tub & Parking is located in Key West, just a 18-minute walk from Key West Aquarium and one mile from Mallory Dock.

From $1,137.99 per night
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Duval Street Suite w kitchen and shared heated pool is located in Key West, just a 15-minute walk from Mallory Dock and 0.9 miles from Mallory Square.

From $250.58 per night

Southern Palms offers accommodations in Key West, a 11-minute walk from Key West Aquarium and 0.6 miles from Mallory Dock.

From $3,324.60 per night
Scored out of 10, guest rating 5.3
Fair - What previous guests thought, 3 reviews

Coconut Palm offers accommodations in Key West, a 11-minute walk from Key West Aquarium and 0.6 miles from Mallory Dock. This property offers a private pool and free Wifi.

From $1,402.09 per night
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Just a 14-minute walk from Key West Aquarium and 0.7 miles from Mallory Dock, Contra House -Luxury Home With Pool features accommodations in Key West with a garden.

From $1,798.71 per night
Scored out of 10, guest rating 7.7
Good - What previous guests thought, 122 reviews

Centrally located in Key West's Old Town, this intimate Florida inn offers bright, tropical rooms. It is 4 blocks from the beach and 2 blocks to dining on Duval Street.

From $291.38 per night
Scored out of 10, guest rating 7.0
Good - What previous guests thought, 7 reviews

Curry House Room 6 is located in Key West, just a 13-minute walk from Mallory Dock and 0.7 miles from Mallory Square. Guests staying at this apartment have access to free Wifi and a patio.

From $614.76 per night

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

Traveler's Palm

Downtown Key West, Key West
Free cancellation options available
Scored out of 10, guest rating 7.8
Good - What previous guests thought, 45 reviews

Traveler's Palm offers accommodations in Key West, a 11-minute walk from Key West Aquarium and 0.6 miles from Mallory Dock. This apartment features air-conditioned accommodations with a patio.

From $574.93 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

The Collins on Duval is located in Key West, just a 9-minute walk from Mallory Dock and half a mile from Mallory Square. This apartment offers air-conditioned accommodations with free Wifi.

From $1,034.79 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, 26 reviews

Duval Dream Loft on Duval is located in Key West, just a 9-minute walk from Mallory Dock and half a mile from Mallory Square. This apartment features air-conditioned accommodations with free Wifi.

From $966.08 per night

Curry House - Room 2

Downtown Key West, Key West
Free cancellation options available

Curry House - Room 2 is located in Key West, just a 13-minute walk from Mallory Dock and 0.7 miles from Mallory Square. Guests staying at this apartment have access to free Wifi and a patio.

From $480.09 per night

Curry House - Room 1

Downtown Key West, Key West
Free cancellation options available
Scored out of 10, guest rating 6.4
Pleasant - What previous guests thought, 7 reviews

Located in the center of Key West, a 12-minute walk from Simonton Street Beach, Curry House - Room 1 has air-conditioned rooms and free WiFi.

From $502.09 per night

Sunnyside Up

Downtown Key West, Key West
Free cancellation options available
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 4 reviews

Sunnyside Up offers accommodations in Key West, 1.5 miles from Key West Aquarium and 1.6 miles from Mallory Dock. Both free Wifi and parking on-site are available at the apartment free of charge.

From $1,145.81 per night

Nyah - Adult Exclusive

Downtown Key West, Key West
Free cancellation options available
Scored out of 10, guest rating 7.4
Good - What previous guests thought, 1,765 reviews

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

From $236.35 per night
Scored out of 10, guest rating 8.2
Very Good - What previous guests thought, 11 reviews

Mesa House, Dos -Unreal Location is located in Key West, just a 9-minute walk from Duval Street and 0.7 miles from Ernest Hemingway Home and Museum.

From $951.86 per night

FAQ about vacation rentals in Key West

Vacation Rentals That Guests Love in Key West

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Avg. price/night: $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: $448.88
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 342 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: $448.88
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 342 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: $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 traveler