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 holiday homes

Tropical Utopia by RENT KEY WEST VACATIONS -Quiet/Gated/Pool/Balcony/Pet friendl

Tropical Utopia by RENT KEY WEST VACATIONS -Quiet/Gated/Pool/Balcony/Pet friendl
Old Town Key West
8.8 out of 10, Excellent, (15 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.
Tropical Utopia by RENT KEY WEST VACATIONS -Quiet/Gated/Pool/Balcony/Pet friendl

Road's End | Prime Old Town Location! Updated Home w/ Pool

Road's End | Prime Old Town Location! Updated Home w/ Pool
Old Town Key West
9.8 out of 10, Exceptional, (8 reviews)
"The courtyard was peaceful and perfect for breakfasts in the morning and board games in the evening. Location is close enough to Duval for easy access, but just enough removed that you don’t hear a thing! Great for us early birds with small children. "
United States
Dylan
The price is HK$1,939
HK$4,469 total
includes taxes & fees
3 Apr - 4 Apr
Road's End | Prime Old Town Location! Updated Home w/ Pool

Shared Pool & Near Duval - Curry House Room 9

Shared Pool & Near Duval - Curry House Room 9
Old Town Key West
7.2 out of 10, Good, (17 reviews)
"Very clean."
United States
Wendy R.
The price is HK$1,449
HK$3,276 total
includes taxes & fees
22 Apr - 23 Apr
Shared Pool & Near Duval - Curry House Room 9

Paradise found

Paradise found
Stock Island
9.8 out of 10, Exceptional, (36 reviews)
"Great house and location. We have found our rental for our yearly stay in Key West. "
United States
Elizabeth F.
Paradise found

Luxury two floor apartment in prime location of famous Duval Street

Luxury two floor apartment in prime location of famous Duval Street
Old Town Key West
9.6 out of 10, Exceptional, (97 reviews)
"Excellent apartment in a great location. "
United States
Jennifer K.
The price is HK$3,094
HK$6,656 total
includes taxes & fees
7 Apr - 8 Apr
Luxury two floor apartment in prime location of famous Duval Street

Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St

Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St
Old Town Key West
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.
Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St

TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking

TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking
Stock Island
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.
The price is HK$3,526
HK$8,920 total
includes taxes & fees
5 Apr - 6 Apr
TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking

Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (62 reviews)
"This was a beautiful property, great location and awesome amenities. We loved it and will highly recommend it! "
United States
Kim H.
The price is HK$3,024
HK$4,581 total
includes taxes & fees
17 Apr - 18 Apr
Poolside Cottage #411

The Seagate Estate at Lunara Bay

The Seagate Estate at Lunara Bay
Raccoon Key
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 HK$7,010
HK$14,346 total
includes taxes & fees
22 Apr - 23 Apr
The Seagate Estate at Lunara Bay

Shared Pool & Parking - The Cottage at James House

Shared Pool & Parking - The Cottage at James House
Key West Historic District
9.6 out of 10, Exceptional, (8 reviews)
"Very convenient to Duval Street and everything in Old Town Key West."
United States
David P.
The price is HK$2,930
HK$4,633 total
includes taxes & fees
1 Apr - 2 Apr
Shared Pool & Parking - The Cottage at James House

The Shellstone House at Solaire Lunara Bay

The Shellstone House at Solaire Lunara Bay
Raccoon Key
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 HK$17,410
HK$29,921 total
includes taxes & fees
15 Apr - 16 Apr
The Shellstone House at Solaire Lunara Bay

Capmar House by Brightwild Huge Home Pool

Capmar House by Brightwild Huge Home Pool
2.0 star property
Raccoon Key
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 HK$9,400
HK$15,665 total
includes taxes & fees
20 Apr - 21 Apr
Capmar House by Brightwild Huge Home Pool

Capmar House at Lunara Bay

Capmar House at Lunara Bay
Raccoon Key
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 traveller
The price is HK$6,877
HK$14,173 total
includes taxes & fees
20 Apr - 21 Apr
Capmar House at Lunara Bay

Slice of Paradise

Slice of Paradise
Stock Island
The price is HK$2,320
HK$4,782 total
includes taxes & fees
18 Apr - 19 Apr
Slice of Paradise

Poolside Cottage #412

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

Gone Coastal

Gone Coastal
Stock Island
9.8 out of 10, Exceptional, (21 reviews)
"Great place , clean and close to everything!"
United States
april
The price is HK$3,126
HK$5,798 total
includes taxes & fees
12 Apr - 13 Apr
Gone Coastal

Southernmost Retreat | On Duval! With Hot Tub, Patio

Southernmost Retreat | On Duval! With Hot Tub, Patio
Old Town Key West
9.8 out of 10, Exceptional, (22 reviews)
"Great apartments, very clean and easy comms with the host. Perfect location, will likely be back!"
United States
Steve
The price is HK$4,514
HK$10,264 total
includes taxes & fees
12 Apr - 13 Apr
Southernmost Retreat | On Duval! With Hot Tub, Patio

Key West Lighthouse Suite

Key West Lighthouse Suite
Old Town Key West
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.
The price is HK$7,169
HK$8,976 total
includes taxes & fees
7 Apr - 8 Apr
Key West Lighthouse Suite

Altair House at Lunara Bay

Altair House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (13 reviews)
"Great house. Large space, everything you need is there. "
United States
CRIMSON A.
The price is HK$12,325
HK$22,914 total
includes taxes & fees
20 Apr - 21 Apr
Altair House at Lunara Bay

BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL

BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL
Key West Historic District
10.0 out of 10, Exceptional, (121 reviews)
"Really great location, friendly accommodating hosts. Just lovely."
United States
David L.
The price is HK$5,289
HK$12,117 total
includes taxes & fees
9 Apr - 10 Apr
BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL
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

Find out more about Key West

Key West Vacation Homes information

Number of reviews
634
Accommodation
1043 Vacation Homes
Lowest Price
HK$3,276
Highest Price
HK$29,921

Explore a world of travel with Expedia