Search Vacation Homes in Key West

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Key West vacation homes

9.8 out of 10, Exceptional, (8 reviews)
"First class, attentive customer service. Prime location. Attractive setting. Easy access. Complimentary airport transportation. "
United States
Cynthia
Road's End | Prime Old Town Location! Updated Home w/ Pool
9.0 out of 10, Wonderful, (188 reviews)
"Great location for &10 Uber to anywhere"
United States
Barbara
The price is AED 1,074
AED 1,921 total
includes taxes & fees
26 Mar - 27 Mar
SPECIALS 4-4 to 6th @225 lod+ 4-20 to 25 + 4-28 to 5-1 @209 lod+kitch+beach
8.6 out of 10, Excellent, (13 reviews)
"This place was great!!! Location was walking distance to everything. The pool was amazing , it felt like our own little resort. We enjoyed having coffee on the patio and watching the birds and iguanas in the trees. "
United States
keri c.
The price is AED 1,078
AED 2,478 total
includes taxes & fees
31 Mar - 1 Apr
Tropical Utopia by RENT KEY WEST VACATIONS -Quiet/Gated/Pool/Balcony/Pet friendl

Vacation Home in Old Town Key West

Shared Pool & Near Duval - Curry House Room 9
7.2 out of 10, Good, (17 reviews)
"Very clean."
United States
Wendy R.
Shared Pool & Near Duval - Curry House Room 9

Vacation Home in Stock Island

Paradise found
9.8 out of 10, Exceptional, (34 reviews)
"Great house and location. We have found our rental for our yearly stay in Key West. "
United States
Elizabeth F.
Paradise found
10.0 out of 10, Exceptional, (17 reviews)
"We stayed for a week and the condo was perfect. Beautifully decorated & very clean. The balconies were an added plus. It’s a perfect location for access to the pool. Roostica is a great Italian restaurant in walking distance. And a delicious French bakery nearby too."
United States
Joan Z.
TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking

Vacation Home in Key West

Poolside Cottage #411
9.8 out of 10, Exceptional, (62 reviews)
"Great little condo - perfect for our family to visit Key West! "
United States
Stephanie A.
Poolside Cottage #411
9.4 out of 10, Exceptional, (50 reviews)
"Loved the location of this property. It is close to everything. It is a little confusing to find the property and the parking and where to load and unload our belongs but the stay was very enjoyable. I love walking downtown to Mallory Square and Duval Street. I would have liked it better if the front door had a shutter or blind on it. "
United States
Kathryn J.
The price is AED 1,322
AED 3,497 total
includes taxes & fees
2 Apr - 3 Apr
Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St
8.8 out of 10, Excellent, (201 reviews)
"Close to everything and still quiet and peaceful. "
United States
Brian
Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK
9.6 out of 10, Exceptional, (97 reviews)
"Excellent apartment in a great location. "
United States
Jennifer K.
Luxury two floor apartment in prime location of famous Duval Street

Vacation Home in Raccoon Key

The Seagate Estate at Lunara Bay
10.0 out of 10, Exceptional, (22 reviews)
"Great place and great hosts. However the pool never heated and couldn’t get anyone out to look at it. Overall an amazing stay and would definitely return."
United States
Austin S.
The price is AED 2,935
AED 6,280 total
includes taxes & fees
31 Mar - 1 Apr
The Seagate Estate at Lunara Bay

Vacation Home in Raccoon Key

Capmar House by Brightwild Huge Home Pool
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"
France
Karen
The price is AED 4,009
AED 6,897 total
includes taxes & fees
20 Apr - 21 Apr
Capmar House by Brightwild Huge Home Pool

Vacation Home in Raccoon Key

Capmar House at Lunara Bay
9.8 out of 10, Exceptional, (29 reviews)
"The property had all the comforts of home. Plus, being able to enjoy the heated pool even through the overcast and windy conditions! The tropical landscaping and the dock on the bay was awesome!Would definitely recommend!!!"
United States
Anonymous traveler
The price is AED 2,935
AED 6,280 total
includes taxes & fees
14 Apr - 15 Apr
Capmar House at Lunara Bay
9.8 out of 10, Exceptional, (21 reviews)
"This place is a hidden gem! We didn’t use the hot tub, but the place was clean and location was perfect! We will be coming back for sure! Loved the fact that we were able to check in a little early as well!"
United States
Mark
Southernmost Retreat | On Duval! With Hot Tub, Patio

Vacation Home in Key West

Poolside Cottage #412
9.4 out of 10, Exceptional, (31 reviews)
"Everything you need for a great stay!!"
United States
Karen D.
Poolside Cottage #412

Vacation Home in Key West Historic District

Meadows Manor | Elegant Oasis with Private Pool
9.4 out of 10, Exceptional, (14 reviews)
"Beautiful home! Well stocked! Quiet yet walkable area"
United States
Ali
Meadows Manor | Elegant Oasis with Private Pool

Vacation Home in Old Town Key West

Key West Lighthouse Suite
9.8 out of 10, Exceptional, (61 reviews)
"We stayed at this location for a four day weekend. We will definitely be back."
United States
Keith D.
Key West Lighthouse Suite

Vacation Home in Raccoon Key

The Shellstone House at Solaire Lunara Bay
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful home with great outdoor space and we loved the pool and private dock"
United States
Sharon L.
The price is AED 4,771
AED 9,772 total
includes taxes & fees
26 Mar - 27 Mar
The Shellstone House at Solaire Lunara Bay

Vacation Home in Key West Historic District

Shared Pool & Parking - The Cottage at James House
9.6 out of 10, Exceptional, (8 reviews)
"Very convenient to Duval Street and everything in Old Town Key West."
United States
David P.
Shared Pool & Parking - The Cottage at James House

Vacation Home in Stock Island

Gone Coastal
9.8 out of 10, Exceptional, (21 reviews)
"Great place , clean and close to everything!"
United States
april
Gone Coastal
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

Top Key West Hotel Reviews