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

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Check availability on Windley Key 4 Star Hotels

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Our top choices for Windley Key 4-star hotels

A beach resort with a calm pool, lounge chairs, and palm trees.

1. Reefhouse Resort & Marina

Key Largo

Vince

HK$2,245 total

includes taxes & fees

29 Nov - 30 Nov

A table with a glass pitcher, a glass with a slice of lime, and a plate with raspberries and a sprig of rosemary.

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

Key Largo

Damion

HK$2,754 total

includes taxes & fees

29 Nov - 30 Nov

An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

3. Islander Resort

Matecumbe

DEBORAH

HK$2,154 total

includes taxes & fees

15 Nov - 16 Nov

A wooden deck with two lounge chairs, a table with two glasses of champagne and red roses, and a view of the beach and ocean.

4. Amara Cay Resort

Matecumbe

Amir

HK$2,056 total

includes taxes & fees

15 Nov - 16 Nov

A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.

5. Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Islamorada

Liosbel

HK$2,401 total

includes taxes & fees

29 Nov - 30 Nov

An aerial view of a resort with a large pool, palm trees, and a beach.

6. Playa Largo Resort & Spa, Autograph Collection

Rock Harbor

Jorge

HK$2,752 total

includes taxes & fees

29 Nov - 30 Nov

A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.

7. La Siesta Resort & Villas

Matecumbe

Brianne

HK$1,937 total

includes taxes & fees

15 Nov - 16 Nov

A wooden deck with a thatched-roof gazebo, overlooking a clear blue sea.

8. Condo in the Keys

Tavernier

Angela

9. Florida Keys Getaway w/ Stunning Ocean Views

Long Key

A beachside patio with outdoor seating, palm trees, and a view of the marina.

10. Key Largo Condo - Community Pool, Marina & Beach!

Key Largo

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Explore similar 5-star hotels

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

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

HK$1,421

HK$2,172 total

19 Nov - 20 Nov

includes taxes & fees

9.2/10 Wonderful! (1,511 reviews)

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Pool Spa Hot tub Breakfast included Waterpark

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

Top Windley Key Hotel Reviews

Islander Resort

10/10 Excellent

"We absolutely loved our stay at Islander! It was such a peaceful, relaxing resort, and we’re so glad we chose it for our honeymoon. The staff was incredibly helpful and welcoming, and the shuttle service was a wonderful perk for getting to and from nearby restaurants. We also really enjoyed the resort’s amenities, especially kayaking, fishing, and bike riding. Everything from check-in to check-out was easy and seamless, making our stay that much more enjoyable. We would definitely stay at Islander again and highly recommend it to anyone looking for a relaxing getaway!"

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