Holiday Homes in Windley Key
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Our top choices for Windley Key holiday homes
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
Beachside Retreat w/ Pool, Boat Ramp Dock for RentKey Largo
9.6 out of 10, Exceptional, (45)
"We absolutely loved it! "
Emily B.
The price is AU$513
includes taxes & fees
15 Dec - 16 Dec
Charming Home in Key Largo
Charming Home in Key LargoKey Largo
9.8 out of 10, Exceptional, (28)
"It was clean and a very nice place to stay. Plenty of room and awesome amenities."
Eric M.
The price is AU$721
includes taxes & fees
28 Dec - 29 Dec
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
New Tiny Home- Paddle Boards, Kayaks, Pool, MarinaKey Largo
9.6 out of 10, Exceptional, (82)
"The place was clean and nice, no problems at all. Plenty of room for my family. Wish we could have stayed longer!"
Brad W.
The price is AU$606
includes taxes & fees
15 Dec - 16 Dec
Casa Largo
Casa LargoKey Largo
9.0 out of 10, Wonderful, (129)
"We stayed in 2 vrbo properties while in Florida. This one met and exceeded our expectations. We would stay again without hesitation."
Kelly M.
The price is AU$811
includes taxes & fees
12 Dec - 13 Dec
NEW ! Marvelous 2-bedroom house with Marina in Key Largo
NEW ! Marvelous 2-bedroom house with Marina in Key LargoKey Largo
10.0 out of 10, Exceptional, (44)
"Good location. Lagoon and pool right outside door. "
Debra C.
The price is AU$792
includes taxes & fees
15 Dec - 16 Dec
Lovely Bungalow w/ Plenty Of Shade at Largo Resort
Lovely Bungalow w/ Plenty Of Shade at Largo ResortKey Largo
10.0 out of 10, Exceptional, (17)
"Our bungalow was very clean and the beds were very comfortable! It was almost like we we're on our own private island and my 8 year old loved it! We hope to come back on our next visit!"
Elizabeth M.
The price is AU$1,243
includes taxes & fees
24 Dec - 25 Dec
Tranquil Bungalow at the Beautiful at Largo Resort
Tranquil Bungalow at the Beautiful at Largo ResortKey Largo
9.6 out of 10, Exceptional, (7)
"10/10! This property itself is secluded and very safe. The pool and views were breathtaking. The complimentary paddle boards and bicycles were fun and just an extra service that bettered our experience. The employees were amazing, kind, and professional. The bungalow was so comfortable and smelt amazing when we entered. Beds were comfortable and the little kitchen was used! Plates, silverwear, & cups were provided thankfully. The host!!!! 100/10. Thank you!!!! She was able to provide a nice...
Nancy H.
The price is AU$1,020
includes taxes & fees
11 Jan - 12 Jan 2026
Ohana Cay 2brm/2bth - Book your getaway!
Ohana Cay 2brm/2bth - Book your getaway!Rock Harbor
10.0 out of 10, Exceptional, (92)
"Perfect location and great community. Easy docking at the marina and nice amenities. "
Gene Z.
The price is AU$1,219
includes taxes & fees
3 Jan - 4 Jan 2026
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.
Top Windley Key Hotel Reviews
Chesapeake Beach Resort
10/10 Excellent
Find out more about Windley Key
Windley Key Holiday Homes information
Number of reviews | 1,098 |
|---|---|
Accommodation | 640 Holiday Homes |
Lowest Price | AU$513 |
Highest Price | AU$3,045 |
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