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

Windley Key 5 Stars Hotels

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Check availability on Windley Key 5 Star Hotels

Tonight
2 Oct - 3 Oct
Tomorrow
3 Oct - 4 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Windley Key 5-star hotels

A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.
A spacious lobby with a seating area, a bar, and a large window providing a view of the outdoors.
A tropical resort with a swimming pool, palm trees, and a waterfall.
A hotel room with a large bed, a television, a dining area with chairs, a table, and a view of the ocean.

1. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
United States
RAIBEL
HK$1,169
HK$1,889 total
includes taxes & fees
4 Oct - 5 Oct
Cheeca Lodge & Spa
A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.
A pool area with clear blue water, white lounge chairs, and palm trees.
A beachside patio with a thatched roof, two lounge chairs, and a view of the ocean.
A resort with multiple white buildings, each featuring balconies and surrounded by lush greenery and palm trees.

2. The Islands of Islamorada

The Islands of Islamorada
Matecumbe
United States
Christian
HK$4,096
HK$5,122 total
includes taxes & fees
4 Oct - 5 Oct
The Islands of Islamorada
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Windley Key.
Reefhouse Resort & Marina

Reefhouse Resort & Marina

103800 Overseas Hwy Key Largo FL
HK$1,718
HK$2,247 total
4 Oct - 5 Oct
includes taxes & fees
9.2/10 Wonderful! (1,542 reviews)
Reefhouse Resort & Marina
Baker's Cay Resort Key Largo, Curio Collection by Hilton

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

97000 Overseas Hwy Key Largo FL
HK$2,181
HK$2,886 total
18 Oct - 19 Oct
includes taxes & fees
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Amara Cay Resort

Amara Cay Resort

80001 Overseas Hwy Islamorada FL
HK$1,213
HK$1,938 total
18 Oct - 19 Oct
includes taxes & fees
Amara Cay Resort
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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.

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