Windley Key Vacation Rentals
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Our top choices for Windley Key vacation rentals
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 P24,882
P27,992 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Villa in Matecumbe
The Islands of Islamorada9.8 out of 10, Exceptional, (70)
"Great for family vacation with kids. love it"
Dixania
The price is P35,777
P43,487 total
includes taxes & fees
Jan 5 - Jan 6, 2026
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
Houseboat in Islamorada
Treasure Harbor9.0 out of 10, Wonderful, (118)
"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, (598)
"Property was nice and easy to navigate, ocean view room was extra nice to have!"
Lisa
The price is P8,980
P13,148 total
includes taxes & fees
Jan 11 - Jan 12, 2026
The price is P73,977
P83,224 total
includes taxes & fees
Jan 1 - Jan 2, 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
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