Search Holiday Rentals in Key West

    price find illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Save instantly and earn perks with One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Top Holiday Rentals in Key West

Kingfish Keep | Lively Escape on Duval! Balcony!

10.0 out of 10, Exceptional, (15)
"Awesome location with excellent communication. "
The price is £272
includes taxes & fees
23 Jul - 24 Jul
Kingfish Keep | Lively Escape on Duval! Balcony!

Paradise found

9.8 out of 10, Exceptional, (26)
"Clean, quiet and great location near Key West. "
The price is £354
includes taxes & fees
10 Aug - 11 Aug
Paradise found

Poolside Cottage #411

9.8 out of 10, Exceptional, (47)
"Lovely home to stay in for a couple of nights on Key West"
The price is £260
includes taxes & fees
30 Jul - 31 Jul
Poolside Cottage #411

Duval Street Retreat | Dog-Friendly Home w/ Hot Tub, Patio, & Parking

9.8 out of 10, Exceptional, (17)
"We loved our hideaway location! Unit was clean and well stocked with everything we needed. Easy access, great directions and a parking space too.We will return again! "
Duval Street Retreat | Dog-Friendly Home w/ Hot Tub, Patio, & Parking

Poolside Cottage #412

9.2 out of 10, Wonderful, (24)
"The property and our place was really nice. Would definitely stay again. "
The price is £280
includes taxes & fees
3 Aug - 4 Aug
Poolside Cottage #412

Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED

9.6 out of 10, Exceptional, (107)
"Very comfortable house in a great location. "
The price is £438
includes taxes & fees
17 Jul - 18 Jul
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED

Wahoo Way | Charming Hideaway On Duval Street!

9.0 out of 10, Wonderful, (16)
"Small place, but clean and everything needed for 2 people to stay I "
The price is £202
includes taxes & fees
23 Jul - 24 Jul
Wahoo Way | Charming Hideaway On Duval Street!

Yellowfin Ledge | Inviting Getaway On Duval! Balcony!

9.4 out of 10, Exceptional, (17)
"Well worth it, located to perfection. "
Yellowfin Ledge | Inviting Getaway On Duval! Balcony!

The Mesa House by Brightwild Close to Duval

2.0 star property
The price is £751
includes taxes & fees
20 Jul - 21 Jul
The Mesa House by Brightwild Close to Duval

Gone Coastal

9.8 out of 10, Exceptional, (16)
"The property was clean and we enjoyed our stay. We especially enjoyed the balcony by our bedroom. "
Gone Coastal

Pescado Penthouse | Vibrant Retreat Overlooking Duval Street!

10.0 out of 10, Exceptional, (4)
"Great location and very nice place."
Pescado Penthouse | Vibrant Retreat Overlooking Duval Street!

Harbor Walk Hideaways | Group Compound In Old Town!

10.0 out of 10, Exceptional, (3)
"I come to Key West often. This is the best location and property I’ve stayed in. Everything was wonderful. I will book this every single time I come. it is perfect for big families, couples or a group of friends. "
The price is £739
includes taxes & fees
22 Jul - 23 Jul
Harbor Walk Hideaways | Group Compound In Old Town!

Capmar House by Brightwild Huge Home Pool

2.0 star property
10.0 out of 10, Exceptional, (1)
"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"
The price is £1,682
includes taxes & fees
3 Aug - 4 Aug
Capmar House by Brightwild Huge Home Pool

Waterfront Luxury Home - Tidelands House

2.0 star property
The price is £2,753
includes taxes & fees
20 Jul - 21 Jul
Waterfront Luxury Home - Tidelands House

Grand Admiral - 46’ 2 Cabin Yacht

The price is £674
includes taxes & fees
17 Jul - 18 Jul
Grand Admiral - 46’ 2 Cabin Yacht

Dog-friendly Key West Cottage with Private Hot Tub & Unbeatable Location

9.0 out of 10, Wonderful, (178)
"Comfortable no frills 3 bedroom home. Close to great bars and restaurants. Would recommend for the location "
The price is £431
includes taxes & fees
29 Jul - 30 Jul
Dog-friendly Key West Cottage with Private Hot Tub & Unbeatable Location

Palmgale House in Key West

2.0 star property
The price is £1,974
includes taxes & fees
20 Jul - 21 Jul
Palmgale House in Key West

Parking, Pool & Pet Friendly - Larkshine House

2.0 star property
10.0 out of 10, Exceptional, (5)
"Great Property, even better than the pictures. Mind you, we went in early March, so we didn't get to swim or crank up the grill or anything so, we can't speak to that but our team loved every bit of the property and it suited our needs. The property was new and the only thing the team complained about was the hot water. It didn't get very hot. But other than that, we'd rent here again."
The price is £2,685
includes taxes & fees
30 Jul - 31 Jul
Parking, Pool & Pet Friendly - Larkshine House

Brand New Build Larkshine House - Pool

2.0 star property
The price is £2,446
includes taxes & fees
20 Jul - 21 Jul
Brand New Build Larkshine House - Pool

Luxury two floor apartment in prime location of famous Duval Street

9.6 out of 10, Exceptional, (82)
"Perfect place to stay. Great location. "
The price is £550
includes taxes & fees
11 Aug - 12 Aug
Luxury two floor apartment in prime location of famous Duval Street
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.
Save an average of 15% on thousands of hotels when you're signed in

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?

THE DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!: This highly rated holiday home rental in Key West is located in the city centre, and offers a BBQ, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Some other homes for rent in Key West include Harbor Walk Hideaways | Group Compound In Old Town! and SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!.

How many holiday rentals will I find in Key West?

With 1352 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.