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

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 NZ$613
includes taxes & fees
3 Nov - 4 Nov
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, (1,321 reviews)
"Super clean resort."
United States
Danielle
The price is NZ$418
includes taxes & fees
20 Oct - 21 Oct
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, (1,477 reviews)
"Staff is very helpful, rooms are clean, and there is a lot to do on the property!"
United States
Morgan
The price is NZ$468
includes taxes & fees
3 Nov - 4 Nov
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 NZ$313
includes taxes & fees
14 Oct - 15 Oct
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, (1,004 reviews)
"Everything was amazing!!! Beautiful hotel and great location."
United States
Jorge
The price is NZ$628
includes taxes & fees
1 Nov - 2 Nov
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 NZ$469
includes taxes & fees
8 Nov - 9 Nov
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 NZ$270
includes taxes & fees
14 Oct - 15 Oct
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
8.6 out of 10, Excellent, (1,185 reviews)
"We loved this place. Will definitely stay there again."
United States
Alan
The price is NZ$692
includes taxes & fees
25 Oct - 26 Oct
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

The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

8/10 Good
"The hotel’s location is fantastic, right on the Gulf side with its own private beach, lounge chairs, and even a small pier. The sunsets were absolutely stunning, and waking up by the water was a real treat. Just a heads up: we booked the economy double room and it was really small; barely enough space for two people and luggage. Still, the outdoor areas more than made up for it."
Betul 1-night trip
Posted 12 hours ago
The Pelican Key Largo Cottages

Find out more about Windley Key

Windley Key Resort information

Number of reviews
5,340
Accommodation
10 Resort
Lowest Price
NZ$270
Highest Price
NZ$692

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