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

4 Star Hotels in Windley Key, Islamorada

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Check availability on Windley Key 4 Star Hotels

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

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 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 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
€278
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.
A resort pool with palm trees, beach chairs, and umbrellas.
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.

2. Amara Cay Resort

Amara Cay Resort
Matecumbe
United States
David A
€205
includes taxes & fees
3 Sept - 4 Sept
Amara Cay Resort
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 spacious living room with large windows, comfortable seating, and decorative plants.
A poolside area with blue chairs and a thatched-roof structure.

3. Reefhouse Resort & Marina

Reefhouse Resort & Marina
Key Largo
United States
Matt
€246
includes taxes & fees
30 Aug - 31 Aug
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 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.

4. Islander Resort

Islander Resort
Matecumbe
United States
Sonia
€295
includes taxes & fees
22 Sept - 23 Sept
Islander 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
Rachel
€286
includes taxes & fees
23 Sept - 24 Sept
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
Dareen
€233
includes taxes & fees
7 Sept - 8 Sept
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 row of colorful beach huts with palm trees in the background.
A beach resort with palm trees, a thatched hut, and a purple building with a window.

7. La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
United States
Brianne
€194
includes taxes & fees
1 Sept - 2 Sept
La Siesta Resort & Villas
A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.
A pool area with clear blue water, white lounge chairs, and palm trees.
A gated entrance to a resort with palm trees and a clear sky.
A beachside patio with a thatched roof, two lounge chairs, and a view of the ocean.

8. The Islands of Islamorada

The Islands of Islamorada
Matecumbe
United States
Christian
€401
includes taxes & fees
30 Aug - 31 Aug
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 clear blue pool with lounge chairs and umbrellas, surrounded by greenery.
A restaurant with a bar area, wooden ceiling, large windows, and potted plants.

9. Condo in the Keys

Condo in the Keys
Tavernier
United States
ann
Condo in the Keys
A modern kitchen with white cabinetry, a built-in oven, and a large island with stools.
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.

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!

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
€207
30 Aug - 31 Aug
includes taxes & fees
9.2/10 Wonderful! (1,410 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 23 hours 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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