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
Aug 29 - Aug 30
Tomorrow
Aug 30 - Aug 31
Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13

Our top choices for Windley Key 4-star hotels

A hammock on a sandy beach with a view of the sea and a tree overhead.
A spacious dining area with high ceilings, wicker furniture, and large windows.
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 table with a glass pitcher, a glass with a slice of lime, and a plate with raspberries and a sprig of rosemary.

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
United States
Vianney
₩326,165
₩442,814 total
includes taxes & fees
Sep 28 - Sep 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.
A beach with palm trees, a dock, and lounge chairs.
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.

2. Amara Cay Resort

Amara Cay Resort
Matecumbe
United States
David A
₩203,458
₩329,542 total
includes taxes & fees
Sep 1 - Sep 2
Amara Cay Resort
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 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.

3. Reefhouse Resort & Marina

Reefhouse Resort & Marina
Key Largo
United States
Matt
₩301,418
₩394,156 total
includes taxes & fees
Aug 30 - Aug 31
Reefhouse Resort & Marina
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 wooden pier leading to a beach with palm trees and a row of beach huts.
A paved pathway leading to a beach with palm trees and a view of the ocean.

4. Islander Resort

Islander Resort
Matecumbe
United States
Sonia
₩335,827
₩470,709 total
includes taxes & fees
Sep 22 - Sep 23
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 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.

5. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
United States
Rachel
₩349,797
₩469,399 total
includes taxes & fees
Sep 2 - Sep 3
Playa Largo Resort & Spa, Autograph Collection
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 beach with palm trees, a clear blue sky, and a calm sea.
An outdoor dining area with round tables and chairs, a thatched roof, and a view of the sea.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
United States
Ana
₩241,134
₩371,927 total
includes taxes & fees
Sep 7 - Sep 8
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio 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 with colorful buildings, kayaks, and lounge chairs.
A row of colorful beach huts with palm trees in the background.

7. La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
United States
Brianne
₩184,877
₩308,639 total
includes taxes & fees
Sep 1 - Sep 2
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 gated entrance to a resort with palm trees and a clear sky.
A resort with multiple white buildings, each featuring balconies and surrounded by lush greenery and palm trees.

8. The Islands of Islamorada

The Islands of Islamorada
Matecumbe
United States
Christian
₩495,482
₩643,198 total
includes taxes & fees
Aug 30 - Aug 31
The Islands of Islamorada
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 wooden deck with a thatched-roof structure, a sign indicating no swimming, and a clear view of the ocean.

9. Condo in the Keys

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

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 beach with kayaks, a palm tree, and a clear sky.
A spacious living room with a dining area, a kitchen in the background, and a TV in the corner.
A spacious kitchen with white cabinets, a large island with bar stools, and pendant lighting.

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

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

12. Lime Key by Florida Keys Luxury Rentals

Lime Key by Florida Keys Luxury Rentals
Buccaneer Point
Lime Key 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
₩205,075
₩331,361 total
Sep 7 - Sep 8
includes taxes & fees
9.2/10 Wonderful! (1,413 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
An archaeological site with stone structures and metal machinery.

Top Windley Key Hotel Reviews

Islander Resort

Islander Resort

10/10 Excellent
"It’s a beautiful property right on the water with very nice pool area and right near everything in Islamorada"
Steven 1-night trip
Posted 1 day ago
Islander Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

10/10 Excellent
"I’d recommend getting breakfast locally instead of the resort’s breakfast. Very friendly and helpful staff."
Dareen 3-night trip
Posted 6 days ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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