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

Windley Key 4 Stars Hotels

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Check availability on Windley Key 4 Star Hotels

Tonight
Oct 13 - Oct 14
Tomorrow
Oct 14 - Oct 15
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

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 poolside area with blue chairs and a thatched-roof structure.
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.

1. Reefhouse Resort & Marina

Reefhouse Resort & Marina
Key Largo
United States
Manny
₩292,321
₩382,260 total
includes taxes & fees
Oct 15 - Oct 16
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 spacious dining area with high ceilings, wicker furniture, and large windows.
A spacious interior with a high ceiling, large windows, and a central chandelier.

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
₩392,938
₩515,644 total
includes taxes & fees
Oct 28 - Oct 29
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 beach with palm trees, a dock, and lounge chairs.
A hotel room with a bed, a sofa, a coffee table, a desk with a lamp, and a view of the ocean.

3. Amara Cay Resort

Amara Cay Resort
Matecumbe
United States
Danielle
₩206,327
₩329,732 total
includes taxes & fees
Oct 18 - Oct 19
Amara Cay Resort
A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.
A coastal resort with a beach, a swimming pool, and multiple buildings.
A resort with a pool, beach, and ocean view.
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
United States
Liosbel
₩319,284
₩456,808 total
includes taxes & fees
Nov 3 - Nov 4
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.
A paved pathway leading to a beach with palm trees and a view of the ocean.
A bar area with a wooden counter, bar stools, and potted plants.
A beachside patio with wooden furniture, a thatched roof, and a view of the ocean.

5. Islander Resort

Islander Resort
Matecumbe
United States
Steven
₩277,638
₩409,945 total
includes taxes & fees
Oct 18 - Oct 19
Islander 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 restaurant with wooden tables and chairs, a bar area, and a view of the sea.

6. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
United States
Jorge
₩353,406
₩471,663 total
includes taxes & fees
Nov 1 - Nov 2
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
₩224,347
₩350,005 total
includes taxes & fees
Nov 8 - Nov 9
La Siesta Resort & Villas
A beach with palm trees, lounge chairs, and a thatched-roof structure.
A spacious living room with a dining area, a sofa, and a coffee table.
A restaurant with a bar area, wooden ceiling, large windows, and potted plants.
A clear blue pool with lounge chairs and umbrellas, surrounded by greenery.

8. Condo in the Keys

Condo in the Keys
Tavernier
United States
Angela
Condo in the Keys
Interior
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 modern kitchen with white cabinets, a microwave, and a dishwasher. There are three bar stools and a large window overlooking the ocean.

9. Florida Keys Getaway w/ Stunning Ocean Views

Florida Keys Getaway w/ Stunning Ocean Views
Long Key
₩755,497
₩1,401,020 total
includes taxes & fees
Oct 28 - Oct 29
Florida Keys Getaway w/ Stunning Ocean Views
A beachside patio with outdoor seating, palm trees, and a view of the marina.
A spacious living room with a dining area, a kitchen in the background, and a TV in the corner.
A kitchen with a large island, stainless steel appliances, and pendant lighting.
A beach with kayaks, a palm tree, and a clear sky.

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

Key Largo Condo - Community Pool, Marina & Beach!
Key Largo
Key Largo Condo - Community Pool, Marina & Beach!
Property grounds
Exterior
Private kitchen
Pool

11. Pineapple Beach by Florida Keys Luxury Rentals

Pineapple Beach by Florida Keys Luxury Rentals
Islamorada
Pineapple Beach by Florida Keys Luxury Rentals
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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
₩265,625
₩396,443 total
Oct 19 - Oct 20
includes taxes & fees
Cheeca Lodge & Spa
The Islands of Islamorada

The Islands of Islamorada

82779 Old Hwy Islamorada FL
₩696,766
₩871,377 total
Oct 15 - Oct 16
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

Amara Cay Resort

Amara Cay Resort

10/10 Excellent
"Beautiful"
Wesley 2-night trip
Posted 1 hour ago
Amara Cay Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

10/10 Excellent
"this was the nicest place i have ever stayed. the staff was so incredibly helpful and the amenities they provide are amazing. will definitely stay here again. 10/10"
Sadie 9-night trip
Posted 1 day ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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