Windley Key Resorts

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

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

In two weeks

In one month

In two months

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

Islamorada

Dareen

P16,659 total

includes taxes & fees

Sep 7 - Sep 8

A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.

2. Cheeca Lodge & Spa

Matecumbe

Jessica

P14,842 total

includes taxes & fees

Sep 7 - Sep 8

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

Matecumbe

David A

P14,760 total

includes taxes & fees

Aug 30 - Aug 31

A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.

4. La Siesta Resort & Villas

Matecumbe

Brianne

P13,870 total

includes taxes & fees

Sep 1 - Sep 2

5. Lime Tree Bay Resort

Long Key

Chadwick

P10,547 total

includes taxes & fees

Aug 30 - Aug 31

A beach with a thatched umbrella, lounge chairs, and a clear view of the ocean.

6. Matecumbe Resort

Matecumbe

Anna

P9,331 total

includes taxes & fees

Aug 30 - Aug 31

An aerial view of a resort with a large pool, palm trees, and a beach.

7. Playa Largo Resort & Spa, Autograph Collection

Rock Harbor

Rachel

P20,528 total

includes taxes & fees

Sep 20 - Sep 21

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

Key Largo

Vianney

P19,900 total

includes taxes & fees

Sep 28 - Sep 29

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Top Windley Key Hotel Reviews

Lime Tree Bay Resort

10/10 Excellent

"Everything about Lime Tree was excellent! We can't wait to go back!"

Chesapeake Beach Resort

8/10 Good

"We arrived one hour and twenty minutes before check in and were told there were no available rooms, although I am positive there were clean ready rooms. My husband and I went to the pool and enjoyed some music before checking into our room. Room was clean and comfortable. Continental breakfast served the next morning. The attendance were lovely and seemed happy to be at work. Check out soon after."

The Pelican Key Largo Cottages

8/10 Good

"Extremely helpful staff, really nice people! Everything was nearby and convenient. You can swim, snorkel, and fish right here! Ice maker was very close too. My only issue was is that I wanted a kitchenette. There were two burners but no stove and the refrigerator didn't work. Staff was very helpful by bringing over a mini frig yet I still got charged for the kitchenette price. I would totally stay here again, but I would check out the unit before completing transaction."

Find out more about Windley Key