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

Windley Key 4 Stars Hotels

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Check availability on Windley Key 4 Star Hotels

Tonight
16 Sept - 17 Sept
Tomorrow
17 Sept - 18 Sept
This weekend
18 Sept - 20 Sept
Next weekend
25 Sept - 27 Sept

Our top choices for Windley Key 4-star hotels

1. Reefhouse Resort & Marina

Reefhouse Resort & Marina
Key Largo
United States
Susan
HK$1,718
HK$2,247 total
includes taxes & fees
22 Sept - 23 Sept
Reefhouse Resort & Marina

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
United States
Milagros
HK$1,859
HK$2,524 total
includes taxes & fees
29 Sept - 30 Sept
Baker's Cay Resort Key Largo, Curio Collection by Hilton

3. Amara Cay Resort

Amara Cay Resort
Matecumbe
United States
Amy
HK$1,213
HK$1,938 total
includes taxes & fees
20 Sept - 21 Sept
Amara Cay Resort

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
Canada
Eslita
HK$1,500
HK$2,261 total
includes taxes & fees
23 Sept - 24 Sept
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

5. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
United States
Danilo
HK$2,000
HK$2,683 total
includes taxes & fees
30 Sept - 1 Oct
Playa Largo Resort & Spa, Autograph Collection

6. Islander Resort

Islander Resort
Matecumbe
United States
Sonia
HK$1,740
HK$2,487 total
includes taxes & fees
27 Sept - 28 Sept
Islander Resort

7. La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
United States
Brianne
La Siesta Resort & Villas

8. The Islands of Islamorada

The Islands of Islamorada
Matecumbe
United States
Christian
HK$3,177
HK$4,070 total
includes taxes & fees
24 Sept - 25 Sept
The Islands of Islamorada

9. Condo in the Keys

Condo in the Keys
Tavernier
United States
Angela
Condo in the Keys
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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

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL
HK$1,169
HK$1,889 total
29 Sept - 30 Sept
includes taxes & fees
Cheeca Lodge & Spa
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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

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

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

10/10 Excellent
"We had an excellent stay at Three Waters Resort in Islamorada. Everything about the property was great from start to finish. Our room was very clean, comfortable, and well maintained, and the entire resort was beautiful and inviting. One of the things we really enjoyed was all of the included amenities. We took advantage of the complimentary kayaks, and they also had bikes available for guests to use at no additional charge. It was a great way to get out, explore, and enjoy the area. The fire pits at night were another highlight. Sitting outside by the fire was the perfect way to end the day and really added to the relaxing Keys atmosphere. Overall, we had a fantastic experience. The property was clean, the amenities were excellent, and there honestly wasn’t anything we could complain about. We would absolutely stay at Three Waters again and highly recommend it to anyone visiting Islamorada!"
Eric 2-night trip
Posted 1 day ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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