Search Vacation Homes in Key West

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Vacation Homes in Key West

House on Settler Lane
House, 2 Bedrooms | 1 bedroom, desk, free WiFi

House on Settler Lane

3.5 star property
10.0 out of 10, Exceptional, (9)
"Great place! Great location! Great stay!"
House on Settler Lane
Augusta House
Exterior detail

Augusta House

3.5 star property
Augusta House
Moose Tracks Lodge
Exterior

Moose Tracks Lodge

3.5 star property
Moose Tracks Lodge
Lorelei Cabins
Cabin (Aster) | Private kitchen | Fridge, microwave, oven, stovetop

Lorelei Cabins

3.0 star property
Lorelei Cabins
House on Northview
House, 6 Bedrooms (with Sofa Bed) | Terrace/patio

House on Northview

3.5 star property
House on Northview
Northstar House
Outdoor spa tub

Northstar House

3.5 star property
10.0 out of 10, Exceptional, (1)
Northstar House
Farmstead House
House, 2 Bedrooms | Private kitchen | Fridge, microwave, stovetop, dishwasher

Farmstead House

3.5 star property
10.0 out of 10, Exceptional, (6)
"Farmstead #9 is a beautiful home. It has all the amenities we wanted, is in a great location, and is ridiculously clean and well kept."
Farmstead House
House on Augusta
House, 5 Bedrooms (With Sofa Bed) | Free WiFi

House on Augusta

3.5 star property
House on Augusta
Shorewood House
Sundeck

Shorewood House

3.5 star property
9.0 out of 10, Wonderful, (2)
"Very clean and comfortable. My family had a good yime"
Shorewood House
Walnut Hill
Exterior

Walnut Hill

3.5 star property
9.0 out of 10, Wonderful, (6)
"Clean comfortable and quiet. Nestled in a golf course complex."
Walnut Hill
Valleywood House
Front of property

Valleywood House

3.5 star property
8.8 out of 10, Excellent, (6)
"Neat and well kept. Liked that there was a bathroom for each bedroom. Enjoyed sitting on the back patio in the evening. Very peaceful area. Also enjoyed long walks on the property. Did not have time to use the pool area that we had access to."
Valleywood House
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
Sign in
Sign up, it's free

Top Key West Hotel Reviews

Dubuque Inn & Suites

Dubuque Inn & Suites

10/10 Excellent
"The staff were very nice and wonderful! The hotel was clean and very nice. "
Cliff 3-night trip
Posted 15 hours ago
Dubuque Inn & Suites