Windley Key Resorts

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

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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

Liosbel

P21,478 total

includes taxes & fees

Nov 3 - Nov 4

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

Matecumbe

Danielle

P15,503 total

includes taxes & fees

Oct 18 - Oct 19

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

3. Cheeca Lodge & Spa

Matecumbe

Morgan

P18,640 total

includes taxes & fees

Oct 14 - Oct 15

4. Lime Tree Bay Resort

Long Key

Katie

P10,982 total

includes taxes & fees

Oct 14 - Oct 15

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

5. Playa Largo Resort & Spa, Autograph Collection

Rock Harbor

Jorge

P22,029 total

includes taxes & fees

Nov 1 - Nov 2

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

6. La Siesta Resort & Villas

Matecumbe

Brianne

P16,456 total

includes taxes & fees

Nov 8 - Nov 9

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

7. Matecumbe Resort

Matecumbe

angel

P9,468 total

includes taxes & fees

Oct 14 - Oct 15

A wooden deck with a view of the ocean and a palm tree.

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

Key Largo

Alan

P24,262 total

includes taxes & fees

Oct 27 - Oct 28

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Top Windley Key Hotel Reviews

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."