4 Stars Hotels in Windley Key, Islamorada from CA $218

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Nov 8 - Nov 9
Tomorrow
Nov 9 - Nov 10
Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22

Our top choices for Windley Key 4-star hotels

A beach with thatched umbrellas, palm trees, and blue lounge chairs.

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 CA $309
CA $405 total
includes taxes & fees
Nov 29 - Nov 30
Reefhouse Resort & Marina
A beach with lounge chairs and a pier extending into the water.

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 CA $372
CA $496 total
includes taxes & fees
Nov 29 - Nov 30
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 CA $253
CA $388 total
includes taxes & fees
Nov 15 - Nov 16
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 CA $235
CA $368 total
includes taxes & fees
Nov 15 - Nov 16
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 CA $293
CA $433 total
includes taxes & fees
Nov 29 - Nov 30
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 CA $372
CA $496 total
includes taxes & fees
Nov 29 - Nov 30
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 CA $218
CA $349 total
includes taxes & fees
Nov 15 - Nov 16
La Siesta Resort & Villas
A beach with palm trees, lounge chairs, and a thatched-roof structure.

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!

Top Windley Key Hotel Reviews

A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

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

10/10 Excellent

Beautiful place Great beds Lots of dining options
Canada
Eslita
Reviewed September 12, 2026
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Find out more about Windley Key

If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Windley Key are calling your name. Known for providing first-rate service in amazing locations, each of the Windley Key 4 Stars hotels lets discerning travelers bask in an unforgettable experience.

Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day.

It’s all waiting for you at the top four star hotels in Windley Key. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Windley Key, Islamorada, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Windley Key hotels with 4 Stars provide everything you need to unwind in style.

Explore a world of travel with Expedia