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Top Holiday Rentals in Key West

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very good, (307)
"We had a nice stay. The property was in a great location."
The price is £219
includes taxes & fees
4 Sept - 5 Sept
Hyatt Vacation Club at Sunset Harbor, Key West

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (160)
"The stay was beautiful "
The price is £173
includes taxes & fees
12 Aug - 13 Aug
Aqua Lodges at Hurricane Hole Marina

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

10.0 out of 10, Exceptional, (18)
"We had a wonderful stay here with our kids. Can’t beat the location."
The price is £256
includes taxes & fees
12 Aug - 13 Aug
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (393)
"this was exactly as advertised and close to all the action"
The price is £170
includes taxes & fees
4 Sept - 5 Sept
Steps from Duval, Pool on Site & Bikes Included!

Heart of Downtown Key West Cottage With Off-Street Parking

10.0 out of 10, Exceptional, (133)
"We very much enjoyed our stay at the cottage. Everything you need for a comfortable stay and a location that can't be beat. Also, the off-street parking was a time, money, and sanity saver. Thanks to Marcela and family!"
Heart of Downtown Key West Cottage With Off-Street Parking

COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

9.6 out of 10, Exceptional, (139)
"Confortable b"
The price is £190
includes taxes & fees
6 Aug - 7 Aug
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking

9.6 out of 10, Exceptional, (8)
"The units were perfect and the customer service was amazing. "
The price is £652
includes taxes & fees
31 Aug - 1 Sept
Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking

Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!

9.6 out of 10, Exceptional, (13)
"Great place to stay! Very clean and steps to Duval Ave."
The price is £318
includes taxes & fees
26 Aug - 27 Aug
Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!

HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!

9.6 out of 10, Exceptional, (141)
"Very clean, great location and wonderful amenities!"
The price is £184
includes taxes & fees
6 Aug - 7 Aug
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

9.2 out of 10, Wonderful, (178)
"Place is centrally located which is ideal for walking from place to place. House was very clean and had everything needed for my time spent there"
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

10.0 out of 10, Exceptional, (19)
"The Osprey Unit was terrific! Great location, clean, and most of all- the staff was incredibly kind and helpful."
The price is £255
includes taxes & fees
27 Aug - 28 Aug
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!

10.0 out of 10, Exceptional, (2)
"We absolutely loved our stay at the Delaney house. The pool and outdoor area were lovely and private, the location was excellent and walking distance from fun Key West spots but quiet and cozy, and the beds were all incredibly comfortable! Would definitely recommend this place to everyone!"
DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

10.0 out of 10, Exceptional, (19)
"Will stay here again "
The price is £258
includes taxes & fees
24 Aug - 25 Aug
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very good, (818)
"Great place really nice rooms"
Coconut Mallory Resort And Marina By Kees Vacations

JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!

9.6 out of 10, Exceptional, (161)
"Clean, comfortable and close to everything fun! "
JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!

Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

9.8 out of 10, Exceptional, (295)
"Excellent accommodations, gorgeous condon"
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

Resort View 1BR Suite

2.0 star property
10.0 out of 10, Exceptional, (2)
"Cleanliness "
The price is £256
includes taxes & fees
19 Aug - 20 Aug
Resort View 1BR Suite

WHITEHEAD ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool

9.2 out of 10, Wonderful, (10)
"Great time staying there "
The price is £183
includes taxes & fees
18 Aug - 19 Aug
WHITEHEAD ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool

GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor Suite w/Shared Pool!

9.2 out of 10, Wonderful, (15)
"We had a great time at this property. The owner is super attentive to detail and immediately responds to any questions or requests. You can really tell that they CARE about their property and guests. Property is well cared for and charming. Highly recommend!"
The price is £226
includes taxes & fees
17 Aug - 18 Aug
GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor Suite w/Shared Pool!

Scott's Cottage - Truman @ Duval | Perfect Location! Ideal for Solos &Couples

10.0 out of 10, Exceptional, (8)
"Great location, friendly and helpful hosts, clean, perfect spot for my solo trip!"
The price is £213
includes taxes & fees
6 Aug - 7 Aug
Scott's Cottage - Truman @ Duval | Perfect Location! Ideal for Solos &Couples
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Key West Hotel Reviews

Frequently asked questions

Can I find holiday rentals in Key West?

Yes, there are holiday rentals in Key West close to Mel Fisher Maritime Museum, or you can select a more secluded option if you're looking for a relaxing stay. Travellers who like culture and the arts give Key West high marks for its great live music and entertainment choices. While you're in the area, you can also enjoy the scenic seaside and lively festivals.

What are some of the best holiday rentals that Key West has to offer?

MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!: This highly rated holiday home rental in Key West is located in the city centre, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Some other homes for rent in Key West include Harbor Walk Hideaways | Group Compound In Old Town! and DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!.

How many holiday rentals will I find in Key West?

With 1348 Expedia holiday rentals, you're guaranteed to find just the right place for your Key West stay.

What can I see and do in Key West?

Mel Fisher Maritime Museum and Florida Keys Eco - Discovery Center are a couple of the family-friendly sights, whereas cultural attractions include Ernest Hemingway Home and Museum and Key West Lighthouse and Keeper's Quarters Museum. Duval Street and Harry S. Truman Little White House are other places to visit while you're in town.

What are holiday rentals like in Key West?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Key West. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for family trips.