Search Holiday Rentals in Windley Key
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Our top choices for Windley Key holiday rentals
Houseboat in Islamorada
Treasure Harbor9.0 out of 10, Wonderful, (117)
"I am obsessed with tiny houses and this one floats! It was so relaxing to sit on the deck and enjoy the view. The bed was very comfy and the gentle motion of the water put me right to sleep. The staff are friendly and helpful. Islamorada is beautiful and fun to explore."
Mary
Aparthotel in Matecumbe
Breezy Palms Resort8.8 out of 10, Excellent, (589)
"we stayed in the beach front cottage kitchen was stocked room was clean and the views were great friendly staff
"
Terry
The price is 2.836.231 ₫
4.554.863 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Villa in Matecumbe
The Islands of Islamorada9.8 out of 10, Exceptional, (69)
"Great for family vacation with kids. love it"
Dixania
The price is 16.025.835 ₫
19.479.679 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Aparthotel in Tavernier
Island Bay Resort10.0 out of 10, Exceptional, (141)
"Very quiet and the outdoor spaces are very nice. Staff was very friendly also."
Jacob
The price is 8.799.736 ₫
9.899.703 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Aparthotel in Key Largo
Kings Kamp8.8 out of 10, Excellent, (23)
"Kings Kamp was a charming stay. The owners were friendly and made the stay easy"
Erica
The price is 33.137.164 ₫
37.279.309 ₫ total
includes taxes & fees
1 Jan - 2 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
Waterside Suites & Marina
10/10 Excellent
