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

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Check prices for these dates

Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13
In one month
Sep 25 - Sep 27
In two months
Oct 23 - Oct 25

Our top choices for Windley Key resorts

A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.

1. Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
4.0 star property
Islamorada
9.0 out of 10, Wonderful, (255 reviews)
"Wonderful resort and friendly staff!"
United States
Ana
The price is ₩241,134
₩371,927 total
includes taxes & fees
Sep 7 - Sep 8
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.

2. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,413 reviews)
"Wonderful stay! Friendly staff, clean rooms, highly recommend!"
United States
Jessica
The price is ₩205,075
₩331,361 total
includes taxes & fees
Sep 7 - Sep 8
Cheeca Lodge & Spa
A wooden deck with two lounge chairs, a table with two glasses of champagne and red roses, and a view of the beach and ocean.

3. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,298 reviews)
"Best place to stay !!"
United States
David A
The price is ₩203,458
₩329,542 total
includes taxes & fees
Sep 1 - Sep 2
Amara Cay Resort
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.

4. La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,004 reviews)
"Great place to stay!"
United States
Brianne
The price is ₩184,877
₩308,639 total
includes taxes & fees
Sep 1 - Sep 2
La Siesta Resort & Villas

5. Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.4 out of 10, Exceptional, (1,472 reviews)
"Would stay again!"
United States
Chadwick
The price is ₩154,257
₩235,475 total
includes taxes & fees
Sep 2 - Sep 3
Lime Tree Bay Resort
An aerial view of a resort with a large pool, palm trees, and a beach.

6. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
4.5 star property
Rock Harbor
9.0 out of 10, Wonderful, (1,003 reviews)
"Such a beautiful resort!"
United States
Rachel
The price is ₩349,797
₩469,399 total
includes taxes & fees
Sep 2 - Sep 3
Playa Largo Resort & Spa, Autograph Collection
A beach with a thatched umbrella, lounge chairs, and a clear view of the ocean.

7. Matecumbe Resort

Matecumbe Resort
2.0 star property
Matecumbe
9.0 out of 10, Wonderful, (158 reviews)
"Worth the money."
United States
paul
The price is ₩184,568
₩207,639 total
includes taxes & fees
Aug 30 - Aug 31
Matecumbe Resort
A hammock on a sandy beach with a view of the sea and a tree overhead.

8. Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton
4.0 star property
Key Largo
8.6 out of 10, Excellent, (1,167 reviews)
"Beautiful and great place and a LOT activity for the kids very family hotel"
United States
Vianney
The price is ₩326,165
₩442,814 total
includes taxes & fees
Sep 28 - Sep 29
Baker's Cay Resort Key Largo, Curio Collection by Hilton
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

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"Nice property with great dining options and activities for the whole family."
John 1-night trip
Posted less than an hour ago
Cheeca Lodge & Spa

Find out more about Windley Key

Windley Key Resorts information

Number of reviews
4,127
Accommodation
9 Resorts
Lowest Price
₩207,639
Highest Price
₩469,399