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

Find 5 Star Hotels in Windley Key, FL from $246

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Check availability on Windley Key 5 Star Hotels

Tonight
Oct 24 - Oct 25
Tomorrow
Oct 25 - Oct 26
Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8

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 bar area with a thatched roof, wooden chairs, and a view of the ocean.
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.

1. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
United States
Patricia
$226 nightly
$246 total
Nov 19 - Nov 20
Total with taxes and fees
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.
An aerial view of a resort with multiple bungalow-style buildings, a central swimming pool, and a beach area.
A gated entrance to a resort with palm trees and a clear sky.

2. The Islands of Islamorada

The Islands of Islamorada
Matecumbe
United States
Christian
$552 nightly
$620 total
Oct 26 - Oct 27
Total with taxes and fees
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
$259 nightly
$286 total
Oct 25 - Oct 26
Total with taxes and fees
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
$294 nightly
$331 total
Nov 9 - Nov 10
Total with taxes and fees
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Islander Resort

Islander Resort

82100 Overseas Highway Islamorada FL
$273 nightly
$308 total
Nov 15 - Nov 16
Total with taxes and fees
Islander 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.

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

Top Windley Key Hotel Reviews

Find out more about Windley Key

Windley Key Five Star Hotel Information

If you’re searching for the celebrity treatment, the 5 star hotels in Windley Key are your dreams come true. From sprawling resorts to fancy hot spots, theseWindley Key 5 star hotels immerse each traveler in the most elite experience money can buy. Want to unwind with a VIP-worthy spa treatment? These hotels have the leisure you're looking for.

Interested in sampling world-class cuisine? The on-site restaurants at the 5 stars hotels in Windley Key, Islamorada, let you do just that. You’ll even be able to book a room (or perhaps a penthouse?) at first-rate hotels near the region’s can’t-miss sights and most bustling shopping centers. Plus, many globe-trotters who visit Windley Key five star hotels find incredible rates and deep discounts thanks to Expedia, so you can score a deal without sacrificing an ounce of quality.

Everything you could possibly want (and a few things you didn’t know you needed): That’s what you’ll receive when you stay at Windley Key 5 star hotels.

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