Search Holiday Rentals in Key West

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Check prices for these dates

Tonight
16 Dec - 17 Dec
Tomorrow
17 Dec - 18 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Our top choices for Key West holiday rentals

Front of property
Aqua Lodges at Hurricane Hole Marina

Houseboat in Stock Island

Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, (170)
"Location , staff , and aqua lodge were perfect."
United States
William
The price is 3.196.908 ₫
8.007.069 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Aqua Lodges at Hurricane Hole Marina
Interior
Island View 1BR Residence With Balcony

Aparthotel in Key West

Island View 1BR Residence With Balcony
2.0 star property
10.0 out of 10, Exceptional, (2)
"Great place it is a full apartment with everything you could need and very clean "
United States
Luis
The price is 8.099.984 ₫
11.349.892 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Island View 1BR Residence With Balcony
Terrace/patio
Hyatt Vacation Club at Sunset Harbor, Key West

Apartment in Old Town Key West

Hyatt Vacation Club at Sunset Harbor, Key West
3.5 star property
8.6 out of 10, Excellent, (321)
"Place was great bed was comfy and the water was HOT!!! "
United States
Angela
The price is 7.080.559 ₫
8.854.251 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Hyatt Vacation Club at Sunset Harbor, Key West
Apartment | 1 bedroom, Internet
The Bartlum Luxury Studio In Prime Location

Apartment in Key West Historic District

The Bartlum Luxury Studio In Prime Location
2.0 star property
The price is 18.451.845 ₫
25.553.688 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
The Bartlum Luxury Studio In Prime Location
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

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent
"shuttle"
Laurie 4-night trip
Posted 20 hours ago
DoubleTree Resort by Hilton Grand Key - Key West

Frequently asked questions

Can I find holiday rentals in Key West?

Yes, there are holiday rentals in Key West close to Florida Keys Eco - Discovery Center, 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 lively festivals and great live music. While you're in the area, you can also enjoy the scenic seaside and entertainment choices.

How many holiday rentals will I find in Key West?

With 1129 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?

Florida Keys Eco - Discovery Center and Key West Shipwreck Museum 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.