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

Compare and book 4 Star hotels in Windley Key, Islamorada

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Check availability on Windley Key 4 Star Hotels

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov

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

Reefhouse Resort & Marina
4.5 star property
Key Largo
9.2 out of 10, Wonderful, (1,566 reviews)
"Very nice property, rooms were well appointed, oceanside fire pit was a nice touch."
Canada
Vince
The price is £214
includes taxes & fees
29 Nov - 30 Nov
Reefhouse Resort & Marina
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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
4.0 star property
Key Largo
8.8 out of 10, Excellent, (1,200 reviews)
"Very relaxing the beach was nice and pretty from that side of the property clean rooms staff was nice and helpful they made the stay enjoyable"
United States
Damion
The price is £263
includes taxes & fees
29 Nov - 30 Nov
Baker's Cay Resort Key Largo, Curio Collection by Hilton
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

3. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,162 reviews)
"The entire resort was clean, staff very friendly, bar and restaurant and pools were fabulous! Would definitely stay there again!"
United States
DEBORAH
The price is £206
includes taxes & fees
15 Nov - 16 Nov
Islander Resort
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

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,333 reviews)
"Great location as well."
United States
Amir
The price is £186
includes taxes & fees
15 Nov - 16 Nov
Amara Cay Resort
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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
4.0 star property
Islamorada
9.0 out of 10, Wonderful, (309 reviews)
"Great place to stay!"
United States
Liosbel
The price is £229
includes taxes & fees
29 Nov - 30 Nov
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
An aerial view of a resort with a large pool, palm trees, and a beach.

6. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
4.5 star property
Rock Harbor
9.0 out of 10, Wonderful, (1,003 reviews)
"Everything was amazing!!! Beautiful hotel and great location."
United States
Jorge
The price is £263
includes taxes & fees
29 Nov - 30 Nov
Playa Largo Resort & Spa, Autograph Collection
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.

7. La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.6 out of 10, Excellent, (1,000 reviews)
"Great place to stay!"
United States
Brianne
The price is £185
includes taxes & fees
15 Nov - 16 Nov
La Siesta Resort & Villas
A wooden deck with a thatched-roof gazebo, overlooking a clear blue sea.

8. Condo in the Keys

Condo in the Keys
4.0 star property
Tavernier
8.2 out of 10, Very good, (17 reviews)
"Love the location "
United States
Angela
Condo in the Keys
Interior

9. Florida Keys Getaway w/ Stunning Ocean Views

Florida Keys Getaway w/ Stunning Ocean Views
4.0 star property
Long Key
Florida Keys Getaway w/ Stunning Ocean Views
A beachside patio with outdoor seating, palm trees, and a view of the marina.

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

Key Largo Condo - Community Pool, Marina & Beach!
4.0 star property
Key Largo
Key Largo Condo - Community Pool, Marina & Beach!
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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
The price is £208 per night from 19 Nov to 20 Nov
£208
19 Nov - 20 Nov
includes taxes & fees
9.2/10 Wonderful! (1,511 reviews)
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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

Islander Resort

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!"
Trevor 4-night trip
Posted 3 days ago
Islander Resort

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