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

Compare and book 5 Star hotels in Windley Key, Islamorada

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Check availability on Windley Key 5 Star Hotels

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov

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.

1. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,511 reviews)
"Great place. Phenomenal food!"
United States
Brandon
The price is £208
includes taxes & fees
19 Nov - 20 Nov
Cheeca Lodge & Spa
A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.

2. The Islands of Islamorada

The Islands of Islamorada
5.0 star property
Matecumbe
9.6 out of 10, Exceptional, (83 reviews)
"We had an AMAZING stay! The staff was wonderful, providing excellent customer service and providing local recommendations for activities and dining. The property is pristine and gorgeous. My only critique would be a lack of on property food options. We will definitely be back."
United States
Catherine
The price is £620
includes taxes & fees
30 Nov - 1 Dec
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
The price is £214 per night from 29 Nov to 30 Nov
£214
29 Nov - 30 Nov
includes taxes & fees
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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

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"Perfect halfway stop off for trip to The Keys . Staff exceptionally helpful.. particularly ‘Fran’ I think that was her name on Front Desk. Great pools and loved the bikes ! Rooms were spacious and comfy beds. Recommend Lorelei Restaurant for something to eat off site ..! Great stay, definitely recommend."
Claire 1-night trip
Posted 6 hours ago
Cheeca Lodge & Spa

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