Holiday Homes in Key West

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Our top choices for Key West holiday homes

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)
"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

SPECIALS 4-4 to 6th @225 lod+ 4-20 to 25 + 4-28 to 5-1 @209 lod+kitch+beach

SPECIALS 4-4 to 6th @225 lod+ 4-20 to 25 + 4-28 to 5-1 @209 lod+kitch+beach
Old Town Key West
9.0 out of 10, Wonderful, (188 reviews)
"Great location for &10 Uber to anywhere"
United States
Barbara
The price is €447
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

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
8.6 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 €582
includes taxes & fees
31 Mar - 1 Apr
Tropical Utopia by RENT KEY WEST VACATIONS -Quiet/Gated/Pool/Balcony/Pet friendl

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 €352
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, (34 reviews)
"Great house and location. We have found our rental for our yearly stay in Key West. "
United States
Elizabeth F.
The price is €632
includes taxes & fees
13 Apr - 14 Apr
Paradise found

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 €1,048
includes taxes & fees
20 Apr - 21 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)
"Great little condo - perfect for our family to visit Key West! "
United States
Stephanie A.
Poolside Cottage #411

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.
The price is €825
includes taxes & fees
2 Apr - 3 Apr
Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St

Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK

Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK
Old Town Key West
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

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 €727
includes taxes & fees
7 Apr - 8 Apr
Luxury two floor apartment in prime location of famous Duval Street

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 Seagate Estate at 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
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 €1,470
includes taxes & fees
14 Apr - 15 Apr
Capmar House at Lunara Bay

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, (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

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

Meadows Manor | Elegant Oasis with Private Pool

Meadows Manor | Elegant Oasis with Private Pool
Key West Historic District
9.4 out of 10, Exceptional, (14 reviews)
"Beautiful home! Well stocked! Quiet yet walkable area"
United States
Ali
The price is €2,054
includes taxes & fees
25 Mar - 26 Mar
Meadows Manor | Elegant Oasis with Private Pool

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.
Key West Lighthouse Suite

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 Shellstone House at Solaire 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.
Shared Pool & Parking - The Cottage at James House

Gone Coastal

Gone Coastal
Stock Island
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.
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Top Key West Hotel Reviews

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Key West Holiday Homes information

Number of reviews
898
Accommodation
1043 Holiday Homes
Lowest Price
€352
Highest Price
€2,054

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