Windley Key Resorts

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sept - 14 Sept

Featured Resorts in Windley Key

Cheeca Lodge & Spa
Relax on the beach with lounge chairs, a shaded hut, and a long pier extending into the calm sea.

Cheeca Lodge & Spa

5.0 star property
9.0 out of 10, Wonderful, (1136)
"Great place "
The price is S$415
includes taxes & fees
20 Jul - 21 Jul
Cheeca Lodge & Spa
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Enjoy ocean views from the large window in this stylish living room, featuring a comfortable sofa and a potted plant.

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

4.0 star property
8.6 out of 10, Excellent, (1004)
"Great spot for famlies! It was quaint and service was top notch when dining. "
The price is S$526
includes taxes & fees
14 Aug - 15 Aug
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Amara Cay Resort
Relax in a serene outdoor seating area with Adirondack chairs around a central fire pit, surrounded by palm trees and ocean views.

Amara Cay Resort

4.0 star property
8.8 out of 10, Excellent, (1237)
"Amazing stay"
The price is S$324
includes taxes & fees
11 Aug - 12 Aug
Amara Cay Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Relax by the oceanfront pool surrounded by palm trees and lounge chairs.

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

3.5 star property
9.0 out of 10, Wonderful, (47)
"This place is a gem. It was beautiful and quiet. "
The price is S$477
includes taxes & fees
11 Aug - 12 Aug
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Playa Largo Resort & Spa, Autograph Collection
Relax by the pool surrounded by palm trees and lounge chairs under a picturesque arched structure.

Playa Largo Resort & Spa, Autograph Collection

4.5 star property
9.0 out of 10, Wonderful, (1004)
"Amazing place, will Definitely be back"
The price is S$474
includes taxes & fees
10 Aug - 11 Aug
Playa Largo Resort & Spa, Autograph Collection
La Siesta Resort & Villas
Relax by the uniquely shaped pool surrounded by palm trees and shaded by umbrellas.

La Siesta Resort & Villas

4.0 star property
8.6 out of 10, Excellent, (1002)
"Pool and bar area very nice and fun for our family "
The price is S$345
includes taxes & fees
18 Aug - 19 Aug
La Siesta Resort & Villas
Lime Tree Bay Resort
Relax by the clear swimming pool surrounded by lounge chairs and umbrellas, with access to the beach and shallow waters.

Lime Tree Bay Resort

3.5 star property
9.2 out of 10, Wonderful, (1081)
"Great resort! We loved the games and hammocks around the property. Loved how we could ride bikes and paddle board right from the resort. "
Lime Tree Bay Resort
Matecumbe Resort
Enjoy a serene beach experience with a tranquil sea and a picturesque pier.

Matecumbe Resort

2.0 star property
8.8 out of 10, Excellent, (59)
"Beautiful resort! All the amenities were great and it was centrally located."
The price is S$211
includes taxes & fees
14 Aug - 15 Aug
Matecumbe Resort
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.
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

Lime Tree Bay Resort

Lime Tree Bay Resort

10/10 Excellent
"Great place"
edwin a 1-night trip
Posted 15 hours ago
Lime Tree Bay Resort