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

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

A dining area with tables set for two, overlooking a beach with palm trees and a sunset view.
A spacious bar area with high ceilings and large windows, offering views of the ocean.
A beach with thatched umbrellas, palm trees, and blue lounge chairs.
A poolside area with blue chairs and a thatched-roof structure.

1. Reefhouse Resort & Marina

Reefhouse Resort & Marina
Key Largo
United States
Susan
₹20,927
₹27,366 total
includes taxes & fees
20 Sept - 21 Sept
Reefhouse Resort & Marina
A wooden deck with a view of the ocean and a palm tree.
A coconut drink with a straw, a cherry, and a slice of fruit on a table by a pool with a waterfall and palm trees in the background.
A modern hotel lobby with large windows, geometric light fixtures, and indoor plants.
A modern hotel room with a large bed, a desk with a lamp, a chair, and a view of the ocean.

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
₹22,646
₹30,744 total
includes taxes & fees
28 Sept - 29 Sept
Baker's Cay Resort Key Largo, Curio Collection by Hilton
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.
An aerial view of a resort with a swimming pool, palm trees, and a dock.
A resort pool with palm trees, beach chairs, and umbrellas.
A beach with palm trees, a dock, and lounge chairs.

3. Amara Cay Resort

Amara Cay Resort
Matecumbe
United States
Amy
₹13,589
₹22,276 total
includes taxes & fees
21 Sept - 22 Sept
Amara Cay Resort
A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.
A resort with a pool, beach, and ocean view.
A coastal resort with a beach, a swimming pool, and multiple buildings.
An outdoor dining area with round tables and chairs, a thatched roof, and a view of the sea.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
Canada
Eslita
₹17,506
₹26,683 total
includes taxes & fees
29 Sept - 30 Sept
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.
A beachside patio with lounge chairs, a table, and a view of the ocean.
A pool area with lounge chairs and umbrellas, a clear sky, and palm trees.
A beach with clear water, a wooden pier, and lounge chairs under a tree.

5. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
United States
Danilo
₹24,367
₹32,682 total
includes taxes & fees
29 Sept - 30 Sept
Playa Largo Resort & Spa, Autograph Collection
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.
A beachside patio with wooden furniture, a thatched roof, and a view of the ocean.
A bar area with a wooden counter, bar stools, and potted plants.
A paved pathway leading to a beach with palm trees and a view of the ocean.

6. Islander Resort

Islander Resort
Matecumbe
United States
Sonia
₹21,200
₹30,300 total
includes taxes & fees
29 Sept - 30 Sept
Islander Resort
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.
A resort with a pool surrounded by palm trees and a view of the ocean.
A beach resort with palm trees, a thatched hut, and a purple building with a window.
A beach with colorful buildings, kayaks, and lounge chairs.

7. La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
United States
Brianne
La Siesta Resort & Villas
A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.
A beachside patio with a thatched roof, two lounge chairs, and a view of the ocean.
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.

8. The Islands of Islamorada

The Islands of Islamorada
Matecumbe
United States
Christian
₹38,701
₹49,581 total
includes taxes & fees
27 Sept - 28 Sept
The Islands of Islamorada
A beach with palm trees, lounge chairs, and a thatched-roof structure.
A clear blue pool with lounge chairs and umbrellas, surrounded by greenery.
A restaurant with a bar area, wooden ceiling, large windows, and potted plants.
A spacious living room with a dining area, a sofa, and a coffee table.

9. Condo in the Keys

Condo in the Keys
Tavernier
United States
Angela
Condo in the Keys
A modern kitchen with white cabinetry, a built-in oven, and a large island with stools.
A modern kitchen with a central island, bar stools, and a ceiling fan.
A beach with clear turquoise water, a wooden pier, and a rocky shoreline.

10. Florida Keys Getaway w/ Stunning Ocean Views

Florida Keys Getaway w/ Stunning Ocean Views
Long Key
Florida Keys Getaway w/ Stunning Ocean Views
A beachside patio with outdoor seating, palm trees, and a view of the marina.
A kitchen with a large island, stainless steel appliances, and pendant lighting.
A spacious kitchen with white cabinets, a large island with bar stools, and pendant lighting.
A spacious living room with a dining area, a kitchen in the background, and a TV in the corner.

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

Key Largo Condo - Community Pool, Marina & Beach!
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
₹12,582
₹21,173 total
30 Sept - 1 Oct
includes taxes & fees
9.2/10 Wonderful! (1,440 reviews)
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 14 hours ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Find out more about Windley Key

Take Your Pick of 4 Star Hotels in Windley Key

The get-go of any holiday starts with choosing a great spot. Windley Key has been a popular destination with guests because it offers so much to do and see. But, "location, location, location" applies to more than just what city where your plane lands. Now that you have a feel for the town, it's time you to get to know your new digs.

Accommodations as Picturesque as Windley Key

Search Expedia.com.sg for the right 4 Star Windley Key Hotel to suit your fancy. Plenty of these people wrote tips to help you select the accommodation that is the right fit for your holiday.You'll be more than glad to get back to your resort every night. Windley Key has dozens of good options in the 4-star hotel range that create the ideal getaway.

A stay at one of these lodgings ensure that whether you are just relaxing after a day of checking out Windley Key or you are ready to lie down for the night, you'll be as comfortable as possible. You won't go without a thing during your stay at one of these accommodations. Visitors have consistently given them high marks for their attentive service. It's no surprise that loads of guests recommend it.

Reserve a 4-Star Hotel in Windley Key Today!

Your trip to Windley Key should be one that you'll reminisce over for years to come, and booking a 4-star hotel will help create memories that are incredible. Make sure to make a reservation soon. With so few hotels, and plenty of people desiring to vacation in Windley Key, you may miss out on your perfect hotel.

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