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
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1
In one month
Nov 13 - Nov 15
In two months
Dec 11 - Dec 13

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, (291 reviews)
"Great place to stay!"
United States
Liosbel
The price is ₩321,425
₩459,872 total
includes taxes & fees
Oct 20 - Oct 21
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
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.

2. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,324 reviews)
"Super clean resort."
United States
Danielle
The price is ₩206,327
₩329,732 total
includes taxes & fees
Oct 19 - Oct 20
Amara Cay Resort
A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.

3. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,478 reviews)
"Staff is very helpful, rooms are clean, and there is a lot to do on the property!"
United States
Morgan
The price is ₩265,625
₩396,443 total
includes taxes & fees
Oct 19 - Oct 20
Cheeca Lodge & Spa
Terrace/patio

4. Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.4 out of 10, Exceptional, (1,539 reviews)
"We will definitely stay here again! Beautiful property that was always clean and peaceful."
United States
Katie
The price is ₩155,259
₩235,135 total
includes taxes & fees
Oct 15 - Oct 16
Lime Tree Bay Resort
An aerial view of a resort with a large pool, palm trees, and a beach.

5. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
4.5 star property
Rock Harbor
9.0 out of 10, Wonderful, (1,001 reviews)
"Everything was amazing!!! Beautiful hotel and great location."
United States
Jorge
The price is ₩353,406
₩471,663 total
includes taxes & fees
Nov 1 - Nov 2
Playa Largo Resort & Spa, Autograph Collection
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.

6. La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.6 out of 10, Excellent, (1,000 reviews)
"Great place to stay!"
United States
Brianne
The price is ₩225,850
₩352,349 total
includes taxes & fees
Nov 1 - Nov 2
La Siesta Resort & Villas
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, (174 reviews)
"A very peaceful place."
United States
angel
The price is ₩180,197
₩202,721 total
includes taxes & fees
Oct 15 - Oct 16
Matecumbe Resort
A wooden deck with a view of the ocean and a palm tree.

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
8.8 out of 10, Excellent, (1,181 reviews)
"We loved this place. Will definitely stay there again."
United States
Alan
The price is ₩393,179
₩515,914 total
includes taxes & fees
Oct 25 - Oct 26
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

Amara Cay Resort

Amara Cay Resort

10/10 Excellent
"Beautiful"
Wesley 2-night trip
Posted 10 hours ago
Amara Cay Resort

Find out more about Windley Key

Windley Key Resorts information

Number of reviews
4,155
Accommodation
9 Resorts
Lowest Price
₩202,721
Highest Price
₩515,914