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 $221

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Check availability on Windley Key 5 Star Hotels

Tonight
Sep 20 - Sep 21
Tomorrow
Sep 21 - Sep 22
Next weekend
Sep 25 - Sep 27
In two weeks
Oct 2 - Oct 4

Our top choices for Windley Key 5-star hotels

Balcony
Property grounds
Lobby
Premium bedding, in-room safe, desk, laptop workspace

1. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
United States
RAIBEL
$196 nightly
$221 total
Sep 21 - Sep 22
Total with taxes and fees
Cheeca Lodge & Spa
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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
Sep 21 - Sep 22
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
$286 nightly
$322 total
Sep 30 - Oct 1
Total with taxes and fees
8.6/10 Excellent! (1,186 reviews)
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Amara Cay Resort

Amara Cay Resort

80001 Overseas Hwy Islamorada FL
$206 nightly
$232 total
Sep 27 - Sep 28
Total with taxes and 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.

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

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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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