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Compare 829 Vacation Homes in Key West with updated reviews, rates, and availability.

Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location

10.0 out of 10, Exceptional, (1)
"Rick and his staff made our girl’s trip worry free. Always available for questions and recommendations. Condo was large, beds comfortable, kitchen well stocked and of course located right on Duval. . As we sit here waiting to leave, other than the roosters, we have no negative comments "
The price is AED 2,417
AED 4,716 total
includes taxes & fees
5 Jan - 6 January 2025
Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

9.0 out of 10, Wonderful, (31)
"Peaceful and paradise!"
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!

9.8 out of 10, Exceptional, (171)
"Accommodations were great. Loft bedroom was a little noisy if people got up early. Noise came straight upstairs. Otherwise accommodations were great. Kitchen well stocked and washer and dryer!! "
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!

INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!

9.6 out of 10, Exceptional, (30)
"This was a very smooth, perfect 5 night visit. The property offered us everything that we could need. It was a short drive to Duval St and all of the activities in Key West yet the property was very peaceful with a wonderful waterfront patio that we sat out on and enjoyed. The hot tub was a nice treat as well. I have to mention the incredible responsiveness of the property manager. Every question that I had they responded to within minutes which was very much appreciated. "
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!

OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!

9.6 out of 10, Exceptional, (75)
"This was our first time staying in an air b&b. We absolutely loved our stay! We wish we would have booked for longer. We highly recommend this place as it was super clean, spacious, and relaxing! We will be back! "
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!

Conch Cove - 3br/3ba with private heated pool and private parking

10.0 out of 10, Exceptional, (1)
"Property had a wonderful heated pool which was lovely since we had a chilly day. It also provides a lot of shade for when it is really hot out. The location was perfect for walking to everything we wanted to see. Rick, the manger was awesome and was there for anything we needed, would recommend this property to anyone seeking to have a holiday in Key West."
The price is AED 3,996
AED 7,238 total
includes taxes & fees
5 Jan - 6 January 2025
Conch Cove - 3br/3ba with private heated pool and private parking

LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool

10.0 out of 10, Exceptional, (185)
"Another fabulous stay at the Lost Shaker of Salt. Great location on Key West. Accommodations met our needs. The pool is delightful. Can’t wait to stay here again when we come back to Key West. "
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool

EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!

9.8 out of 10, Exceptional, (87)
"Loved the house it was awesome for our group plenty of space for our large group. The beds were very comfortable and every thing was clean and looked new. "
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!

~POINCIANA GARDEN~ Casual 1st floor duplex 2 blocks from Duval Street!

9.8 out of 10, Exceptional, (162)
"Loved this light filled little cottage with a huge back porch and yard. It was a great launching pad for our visit to the area. "
~POINCIANA GARDEN~ Casual 1st floor duplex 2 blocks from Duval Street!

Poolside Cottage #411

10.0 out of 10, Exceptional, (33)
"Really nice place to stay. We had a pleasant stay and the property was great "
The price is AED 1,241
AED 1,923 total
includes taxes & fees
8 Jan - 9 January 2025
Poolside Cottage #411

Banana Breeze: Oceanview 4-bedroom home with private pool & lush landscaping!

9.8 out of 10, Exceptional, (97)
"Great place to stay very kid friendly and a short golfcart ride to everything "
Banana Breeze: Oceanview 4-bedroom home with private pool & lush landscaping!

CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!

9.8 out of 10, Exceptional, (110)
"Ok location. 10 minutes to key west. Nice pool"
CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!

Pool & Parking, Near Duval - Poolside Paradise

9.2 out of 10, Wonderful, (11)
"Great location 1/2 block from Duval. Lots of great towels, and pillows! I didn’t know this is two units connected but no connecting door, you access back unit via the pool. We needed both sofa beds but one had broken springs and was unusable. The floors hadn’t been mopped and all of my kids had black feet from walking around barefoot. If you are planning to cook you might want to bring a decent frying pan and a sharp knife. They have plenty of knives but none sharp. The grill didn’t work and...
The price is AED 3,137
AED 5,721 total
includes taxes & fees
7 Jan - 8 January 2025
Pool & Parking, Near Duval - Poolside Paradise

Wahoo Way | Charming Hideaway On Duval Street!

The price is AED 754
AED 1,631 total
includes taxes & fees
24 Dec - 25 Dec
Wahoo Way | Charming Hideaway On Duval Street!

Dec. Spec Only dates 12 (2-5) 12 (8-11) & 12 (14-19) Near beach full kitch

9.6 out of 10, Exceptional, (204)
"Cute, older place in good location, with nice front porch. You can walk, but we rented bikes, and glad we did. Because you have to park on street and only in designated areas, it's hard to find a spot. Place did not seem that clean. Floors were really dirty. Walked 10 steps after getting out of shower and our feet were black!"
Dec. Spec Only dates 12 (2-5) 12 (8-11) & 12 (14-19) Near beach full kitch

Poolside Cottage #412

10.0 out of 10, Exceptional, (14)
"Quiet area of the key west neighbors quiet, nice bike ride to key west and grocery store was close by. Would recommend renting from the resort"
The price is AED 1,241
AED 1,912 total
includes taxes & fees
6 Jan - 7 January 2025
Poolside Cottage #412

NEWLY REMODELED KITCHEN!! PET FRIENDLY! 3 Bedroom 3 bathroom home. Sleeps 8

9.6 out of 10, Exceptional, (196)
"Exactly as advertised with an incredible host. We had a great time in Key West! "
NEWLY REMODELED KITCHEN!! PET FRIENDLY! 3 Bedroom 3 bathroom home. Sleeps 8

SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!

9.8 out of 10, Exceptional, (171)
"Beautiful, well appointed home in a great neighborhood. Great communication and lovely experience!"
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!

CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!

9.6 out of 10, Exceptional, (173)
"Captains Quarters is a beautiful house, great location, walking distance to Duval, clean, heated pool and plenty of amenities to make your stay enjoyable. Would def stay there again. "
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!

HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!

9.8 out of 10, Exceptional, (22)
"Clean, cozy and cute "
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
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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Other property types in Key West

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (105)
"Nice for affordable price "
The price is AED 757
AED 1,368 total
includes taxes & fees
7 Jan - 8 January 2025
Aqua Lodges at Hurricane Hole Marina

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very Good, (286)
"We have been to Hyatt Sunset many times as we own Hyatt Timeshare. Staff is especially friendly and gracious!"
The price is AED 1,739
AED 2,060 total
includes taxes & fees
23 Dec - 24 Dec
Hyatt Vacation Club at Sunset Harbor, Key West

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very Good, (799)
"Great condo for family."
Coconut Mallory Resort And Marina By Kees Vacations
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.