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

Windley Key Resorts

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

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, (306 reviews)
"Great place to stay!"
United States
Liosbel
The price is S$391
includes taxes & fees
29 Nov - 30 Nov
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, (1,497 reviews)
"Great place. Phenomenal food!"
United States
Brandon
The price is S$354
includes taxes & fees
8 Nov - 9 Nov
Cheeca Lodge & Spa
Terrace/patio

3. Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.4 out of 10, Exceptional, (1,561 reviews)
"Very friendly staff, quiet and low key if that’s what you’re looking for"
United States
Mark Blair
The price is S$236
includes taxes & fees
3 Nov - 4 Nov
Lime Tree Bay 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.

4. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,324 reviews)
"Great location as well."
United States
Amir
The price is S$321
includes taxes & fees
15 Nov - 16 Nov
Amara Cay 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 S$449
includes taxes & fees
29 Nov - 30 Nov
Playa Largo Resort & Spa, Autograph Collection
A beach with lounge chairs and a pier extending into the water.

6. 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, (1,202 reviews)
"Very relaxing the beach was nice and pretty from that side of the property clean rooms staff was nice and helpful they made the stay enjoyable"
United States
Damion
The price is S$423
includes taxes & fees
11 Nov - 12 Nov
Baker's Cay Resort Key Largo, Curio Collection by Hilton
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, (182 reviews)
"The room was very clean and had a park area that if traveling with little ones will enjoy."
United States
Adelangele
The price is S$226
includes taxes & fees
10 Nov - 11 Nov
Matecumbe Resort
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.

8. 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 S$316
includes taxes & fees
15 Nov - 16 Nov
La Siesta Resort & Villas
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windley Key Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Excellent stay would definitely stay again"
Lisa D 1-night trip
Posted 4 hours ago
Chesapeake Beach Resort

Find out more about Windley Key

Windley Key Resorts information

Number of reviews
182
Accommodation
9 Resorts
Lowest Price
S$226
Highest Price
S$449

Explore a world of travel with Expedia