Top Resorts in Windley Key in 2026

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

Rp6.130.367 total

includes taxes & fees

3 Nov - 4 Nov

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

Rp4.424.992 total

includes taxes & fees

18 Oct - 19 Oct

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

Rp5.320.250 total

includes taxes & fees

14 Oct - 15 Oct

4. Lime Tree Bay Resort

Long Key

Katie

Rp3.134.502 total

includes taxes & fees

14 Oct - 15 Oct

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

Rp6.287.553 total

includes taxes & fees

1 Nov - 2 Nov

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

6. La Siesta Resort & Villas

Matecumbe

Brianne

Rp4.697.047 total

includes taxes & fees

8 Nov - 9 Nov

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

7. Matecumbe Resort

Matecumbe

angel

Rp2.700.288 total

includes taxes & fees

14 Oct - 15 Oct

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

Rp6.919.927 total

includes taxes & fees

25 Oct - 26 Oct

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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."