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

Find 4 Star Hotels in Windley Key, FL from $233

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Check availability on Windley Key 4 Star Hotels

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

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.
An aerial view of a resort with a large pool, sun loungers, and palm trees.
A beach with thatched umbrellas, palm trees, and blue lounge chairs.
A spacious living room with large windows, comfortable seating, and decorative plants.

1. Reefhouse Resort & Marina

Reefhouse Resort & Marina
Key Largo
Canada
William Dean
$259 nightly
$286 total
Oct 27 - Oct 28
Total with taxes and fees
Reefhouse Resort & Marina
A beach with lounge chairs and a pier extending into the water.
A beachside bar with a thatched roof, palm trees, and a view of the sea.
A spacious interior with a high ceiling, large windows, and a central light fixture.
A resort with multiple buildings, a dock, and clear waters.

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
$294 nightly
$331 total
Nov 9 - Nov 10
Total with taxes and fees
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 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.
A paved pathway leading to a beach with palm trees and a view of the ocean.

3. Islander Resort

Islander Resort
Matecumbe
United States
Bryan
$273 nightly
$308 total
Nov 15 - Nov 16
Total with taxes and fees
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.
An aerial view of a resort with a swimming pool, palm trees, and a dock.
A hotel room with a bed, a sofa, a coffee table, a desk with a lamp, and a view of the ocean.
A beach with palm trees, a dock, and lounge chairs.

4. Amara Cay Resort

Amara Cay Resort
Matecumbe
United States
Ronald
$220 nightly
$248 total
Nov 15 - Nov 16
Total with taxes and fees
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.
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
$304 nightly
$342 total
Nov 2 - Nov 3
Total with taxes and fees
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 restaurant with wooden tables and chairs, a bar area, and a view of the sea.
A beach with clear water, a wooden pier, and lounge chairs under a tree.

6. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
United States
Jorge
$352 nightly
$396 total
Nov 9 - Nov 10
Total with taxes and fees
Playa Largo Resort & Spa, Autograph Collection
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.
A beach with colorful buildings, kayaks, and lounge chairs.
A beach resort with palm trees, a thatched hut, and a purple building with a window.
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
$237 nightly
$266 total
Nov 15 - Nov 16
Total with taxes and fees
La Siesta Resort & Villas
A beach with palm trees, lounge chairs, and a thatched-roof structure.
A wooden deck with a thatched-roof structure, a sign indicating no swimming, and a clear view of the ocean.
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.

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
$207 nightly
$233 total
Nov 1 - Nov 2
Total with taxes and fees
Cheeca Lodge & Spa
The Islands of Islamorada

The Islands of Islamorada

82779 Old Hwy Islamorada FL
$534 nightly
$600 total
Oct 27 - Oct 28
Total with taxes and 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 10 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 16 hours ago
Amara Cay Resort
Islander Resort

Islander Resort

10/10 Excellent
"💜"
Carolyn 7-night trip
Posted 16 hours ago
Islander Resort

Find out more about Windley Key

Windley Key Four Star Hotel Information

When you need to book a room with luxurious amazing amenities and the best rates, the 4 star hotels in Windley Key, Islamorada are incredible options. Known for their extra perks, first-rate service, and fantastic locations, each of the Windley Key 4 star hotels offers the ultimate experience for globe-trotting travelers. Relax in your expertly designed room. Kick back with around-the-clock room service.

Get a good night’s sleep with the ultra-plush bedding, and freshen up in the morning with designer-inspired body products. It’s all available when you stay at one of the top book a four star hotels in Windley Key. What’s more, thanks to Expedia you might even score a cheap great deal on a 4 star hotel in Windley Key, Islamorada, areas near the hottest attractions, so you can plan a sightseeing adventure and take advantage of unbeatable discounts in one fell swoop.

Whether you’re putting together a serene getaway or want to revel in the most vibrant entertainment district, 4 star Windley Key hotels offer everything your heart desires.

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