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 $234

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Check availability on Windley Key 5 Star Hotels

Tonight
Oct 5 - Oct 6
Tomorrow
Oct 6 - Oct 7
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

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
RAIBEL
$218 nightly
$245 total
Oct 13 - Oct 14
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 resort with multiple white buildings, each featuring balconies and surrounded by lush greenery and palm trees.
A pool area with clear blue water, white lounge chairs, and palm trees.
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
$534 nightly
$600 total
Oct 18 - Oct 19
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 6 - Oct 7
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
$327 nightly
$368 total
Oct 18 - Oct 19
Total with taxes and fees
8.6/10 Excellent! (1,178 reviews)
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Amara Cay Resort

Amara Cay Resort

80001 Overseas Hwy Islamorada FL
$208 nightly
$234 total
Oct 18 - Oct 19
Total with taxes and fees
8.8/10 Excellent! (1,322 reviews)
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.

Top Windley Key Hotel Reviews

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"Take a large was more than we expected. It was beautiful. It was clean. The service was amazing. The hotel had the perfect keys vibe. The beach was exactly what we needed. Perfect for group of friends families overall great hotel great food. Great drinks great bar service the rooms for spacious clean valet was super friendly. The staff was kind and cheerful. This place definitely gets five stars."
yusleidy 2-night trip
Posted 10 hours ago
Cheeca Lodge & Spa

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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