A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.

Windley Key Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Windley Key vacation rentals

A beach with palm trees, thatched-roof huts, and lounge chairs.

1. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (785 reviews)
"Such a great place to stay!!"
United States
Gavin
The price is P7,284
P9,211 total
includes taxes & fees
Nov 15 - Nov 16
Breezy Palms Resort
A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

2. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (185 reviews)
"Had a very enjoyable stay at Hemingway House. The place was spotless! All staff were very friendly and helpful. Would highly recommend staying here!"
United States
Diane
The price is P7,892
P17,840 total
includes taxes & fees
Nov 16 - Nov 17
Treasure Harbor
Two hammocks with a view of the sea and a boat in the background.

3. Piece of Paradise

Piece of Paradise
2.0 star property
Key largo
The price is P10,890
P24,033 total
includes taxes & fees
Dec 1 - Dec 2
Piece of Paradise
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 Windley Key Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"The room was very clean and comfortable, my only issue was it was close to the road so all you hear is road traffic. I asked to move rooms but we weren’t able to. The breakfast was nice- homemade omelet and waffles, a selections of items to toast. The bar tender Jose was super nice and very helpful as well as maintenance man Douglas- he was super Friendly. We thought the amenities were great and we would totally stay again!"
Wendy Gail 6-night trip
Posted 15 hours ago
Chesapeake Beach Resort

Find out more about Windley Key

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