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
4 Sept - 6 Sept
In two weeks
11 Sept - 13 Sept
In one month
25 Sept - 27 Sept
In two months
23 Oct - 25 Oct

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)
"I’d recommend getting breakfast locally instead of the resort’s breakfast. Very friendly and helpful staff."
United States
Dareen
The price is NZ$454
includes taxes & fees
7 Sept - 8 Sept
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, (1,406 reviews)
"Wonderful stay! Friendly staff, clean rooms, highly recommend!"
United States
Jessica
The price is NZ$404
includes taxes & fees
2 Sept - 3 Sept
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, (1,296 reviews)
"Best place to stay !!"
United States
David A
The price is NZ$377
includes taxes & fees
2 Sept - 3 Sept
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, (1,001 reviews)
"Great place to stay!"
United States
Brianne
The price is NZ$377
includes taxes & fees
30 Aug - 31 Aug
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, (1,495 reviews)
"Would stay again!"
United States
Chadwick
The price is NZ$287
includes taxes & fees
30 Aug - 31 Aug
Lime Tree Bay Resort
A beach with a thatched umbrella, lounge chairs, and a clear view of the ocean.

6. Matecumbe Resort

Matecumbe Resort
2.0 star property
Matecumbe
9.0 out of 10, Wonderful, (157 reviews)
"Staff very friendly and accommodating Great location (plenty places to eat, fishing charters, Robbie’s just around the corner), boat parking, kayaking/bikes for use. Full size kitchen! Simply amazing for family, fishing trip. Would love to com back soon!"
United States
Anna
The price is NZ$254
includes taxes & fees
30 Aug - 31 Aug
Matecumbe Resort
An aerial view of a resort with a large pool, palm trees, and a beach.

7. 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 NZ$559
includes taxes & fees
20 Sept - 21 Sept
Playa Largo Resort & Spa, Autograph Collection
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, (1,163 reviews)
"Beautiful and great place and a LOT activity for the kids very family hotel"
United States
Vianney
The price is NZ$541
includes taxes & fees
28 Sept - 29 Sept
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

Lime Tree Bay Resort

Lime Tree Bay Resort

10/10 Excellent
"Everything about Lime Tree was excellent! We can't wait to go back!"
Paula 4-night trip
Posted 4 hours ago
Lime Tree Bay Resort

Find out more about Windley Key

Windley Key Resort information

Number of reviews
4,073
Accommodation
10 Resort
Lowest Price
NZ$254
Highest Price
NZ$559

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