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

Four Star Hotels in Windley Key

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Check availability on Windley Key 4 Star Hotels

Tonight
26 Oct - 27 Oct
Tomorrow
27 Oct - 28 Oct
This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

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 living room with large windows, comfortable seating, and decorative plants.
A spacious bar area with high ceilings and large windows, offering views of the ocean.
An aerial view of a resort with a large pool, sun loungers, and palm trees.

1. Reefhouse Resort & Marina

Reefhouse Resort & Marina
Key Largo
Canada
William Dean
RM895
RM1,170 total
includes taxes & fees
27 Oct - 28 Oct
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.
A spacious interior with a high ceiling, large windows, and a central light fixture.
A beach with lounge chairs and a pier extending into the water.
An aerial view of a resort with a central swimming pool surrounded by palm trees and a sandy beach.

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
Alan
RM1,002
RM1,352 total
includes taxes & fees
9 Nov - 10 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.
A bar area with a wooden counter, bar stools, and potted plants.
A wooden pier leading to a beach with palm trees and a row of beach huts.
A beachside patio with wooden furniture, a thatched roof, and a view of the ocean.

3. Islander Resort

Islander Resort
Matecumbe
United States
Bryan
RM765
RM1,159 total
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.
A resort pool with palm trees, beach chairs, and umbrellas.
An aerial view of a resort with a swimming pool, palm trees, and a dock.
A beach with palm trees, a dock, and lounge chairs.

4. Amara Cay Resort

Amara Cay Resort
Matecumbe
United States
Ronald
RM687
RM1,071 total
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.
An outdoor dining area with round tables and chairs, a thatched roof, and a view of the sea.
A coastal resort with a beach, a swimming pool, and multiple buildings.
A beach with palm trees, a clear blue sky, and a calm sea.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
United States
Liosbel
RM977
RM1,398 total
includes taxes & fees
1 Nov - 2 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.
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.
A beachside patio with lounge chairs, a table, and a view of the ocean.

6. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
United States
Jorge
RM1,238
RM1,618 total
includes taxes & fees
9 Nov - 10 Nov
Playa Largo Resort & Spa, Autograph Collection
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.
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.
A resort with a pool surrounded by palm trees and a view of the ocean.

7. La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
United States
Brianne
RM632
RM1,009 total
includes taxes & fees
15 Nov - 16 Nov
La Siesta Resort & Villas
A sunset over a body of water with clouds.
A clear blue pool with lounge chairs and umbrellas, surrounded by greenery.
A beach with palm trees, lounge chairs, and a thatched-roof structure.
A bedroom with a bed, a ceiling fan, a dining table with chairs, and artwork on the walls.

8. 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
RM813
RM1,213 total
31 Oct - 1 Nov
includes taxes & fees
Cheeca Lodge & Spa
The Islands of Islamorada

The Islands of Islamorada

82779 Old Hwy Islamorada FL
RM2,133
RM2,667 total
27 Oct - 28 Oct
includes taxes & fees
The Islands of Islamorada
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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

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

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

10/10 Excellent
"Amazing hotel with lots of on-site amenities and options for dinner. Loved the fishing in the morning."
Forrest 2-night trip
Posted 6 hours ago
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Amara Cay Resort

Amara Cay Resort

10/10 Excellent
"Great property however the rooms could use an update."
Michelle 2-night trip
Posted 12 hours ago
Amara Cay Resort
Islander Resort

Islander Resort

10/10 Excellent
"💜"
Carolyn 7-night trip
Posted 12 hours ago
Islander 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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