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

Windley Key 4 Stars Hotels

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Check availability on Windley Key 4 Star Hotels

Tonight
26 Sept - 27 Sept
Tomorrow
27 Sept - 28 Sept
Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct

Our top choices for Windley Key 4-star hotels

A dining area with tables set for two, overlooking a beach with palm trees and a sunset view.
A spacious bar area with high ceilings and large windows, offering views of the ocean.
A beach with thatched umbrellas, palm trees, and blue lounge chairs.
A poolside area with blue chairs and a thatched-roof structure.

1. Reefhouse Resort & Marina

Reefhouse Resort & Marina
Key Largo
United States
Susan
HK$1,561
HK$2,070 total
includes taxes & fees
27 Sept - 28 Sept
Reefhouse Resort & Marina
A wooden deck with a view of the ocean and a palm tree.
A spacious dining area with high ceilings, wicker furniture, and large windows.
A hammock on a sandy beach with a view of the sea and a tree overhead.
A spacious interior with a high ceiling, large windows, and a central chandelier.

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
United States
Milagros
HK$2,057
HK$2,747 total
includes taxes & fees
29 Sept - 30 Sept
Baker's Cay Resort Key Largo, Curio Collection by Hilton
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.
A beach with palm trees, a dock, and lounge chairs.
A resort pool with palm trees, beach chairs, and umbrellas.
An aerial view of a resort with a swimming pool, palm trees, and a dock.

3. Amara Cay Resort

Amara Cay Resort
Matecumbe
United States
MICHAEL
HK$1,212
HK$1,937 total
includes taxes & fees
28 Sept - 29 Sept
Amara Cay Resort
A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.
A coastal resort with a beach, a swimming pool, and multiple buildings.
A resort with a pool, beach, and ocean view.
A beach with palm trees, a clear blue sky, and a calm sea.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
Canada
Eslita
HK$1,625
HK$2,402 total
includes taxes & fees
6 Oct - 7 Oct
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.
A paved pathway leading to a beach with palm trees and a view of the ocean.
A beachside patio with wooden furniture, a thatched roof, and a view of the ocean.
A wooden pier leading to a beach with palm trees and a row of beach huts.

5. Islander Resort

Islander Resort
Matecumbe
United States
John
HK$2,245
HK$3,099 total
includes taxes & fees
27 Oct - 28 Oct
Islander Resort
An aerial view of a resort with a large pool, palm trees, and a beach.
A restaurant with wooden tables and chairs, a bar area, and a view of the sea.
A pool area with lounge chairs and umbrellas, a clear sky, and palm trees.
A beachside patio with lounge chairs, a table, and a view of the ocean.

6. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
United States
Tania
HK$2,063
HK$2,753 total
includes taxes & fees
11 Oct - 12 Oct
Playa Largo Resort & Spa, Autograph Collection
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.
A row of colorful beach huts with palm trees in the background.
A beach with colorful buildings, kayaks, and lounge chairs.
A resort with a pool surrounded by palm trees and a view of the ocean.

7. La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
United States
Brianne
La Siesta Resort & Villas
A beach with palm trees, lounge chairs, and a thatched-roof structure.
A clear blue pool with lounge chairs and umbrellas, surrounded by greenery.
A restaurant with a bar area, wooden ceiling, large windows, and potted plants.
A spacious living room with a dining area, a sofa, and a coffee table.

8. Condo in the Keys

Condo in the Keys
Tavernier
United States
Angela
Condo in the Keys
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Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Windley Key.
Cheeca Lodge & Spa

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL
HK$1,169
HK$1,888 total
29 Sept - 30 Sept
includes taxes & fees
9.2/10 Wonderful! (1,456 reviews)
Cheeca Lodge & Spa
The Islands of Islamorada

The Islands of Islamorada

82779 Old Hwy Islamorada FL
HK$3,247
HK$4,151 total
1 Oct - 2 Oct
includes taxes & fees
The Islands of Islamorada
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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.

Learn more about Windley Key

Check out the local area in Windley Key—home to attractions like Windley Key Fossil Reef Geological State Park and Hog Heaven.

See all hotels in Windley Key
A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.

Top Windley Key Hotel Reviews

Islander Resort

Islander Resort

8/10 Good
"I liked the fact that our rear outside seating area was quite private because of the trees and bushes growing around the property. Very peaceful and also just a couple of minutes walk from the sea."
norman 4-night trip
Posted 9 hours ago
Islander Resort

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