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

4 Star Hotels in Windley Key, Islamorada

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Windley Key 4 Star Hotels

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

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 spacious living room with large windows, comfortable seating, and decorative plants.

1. Reefhouse Resort & Marina

Reefhouse Resort & Marina
Key Largo
United States
Manny
€257
includes taxes & fees
14 Oct - 15 Oct
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 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.

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
€346
includes taxes & fees
25 Oct - 26 Oct
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.
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.

3. Amara Cay Resort

Amara Cay Resort
Matecumbe
United States
Danielle
€221
includes taxes & fees
18 Oct - 19 Oct
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.

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
€307
includes taxes & fees
3 Nov - 4 Nov
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 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.
A paved pathway leading to a beach with palm trees and a view of the ocean.

5. Islander Resort

Islander Resort
Matecumbe
United States
Steven
€275
includes taxes & fees
18 Oct - 19 Oct
Islander Resort
An aerial view of a resort with a large pool, palm trees, and a beach.
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.
A pool area with lounge chairs and umbrellas, a clear sky, and palm trees.

6. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
United States
Jorge
€315
includes taxes & fees
1 Nov - 2 Nov
Playa Largo Resort & Spa, Autograph Collection
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.
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.
A beach with colorful buildings, kayaks, and lounge chairs.

7. La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
United States
Brianne
€235
includes taxes & fees
8 Nov - 9 Nov
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 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
Interior
A beach with clear turquoise water, a wooden pier, and a rocky shoreline.
A modern kitchen with white cabinets, a microwave, and a dishwasher. There are three bar stools and a large window overlooking the ocean.
A modern kitchen with a central island, bar stools, and a ceiling fan.

9. Florida Keys Getaway w/ Stunning Ocean Views

Florida Keys Getaway w/ Stunning Ocean Views
Long Key
€941
includes taxes & fees
28 Oct - 29 Oct
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 spacious kitchen with white cabinets, a large island with bar stools, 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
Private kitchen
Beach/ocean view
Pool

11. Pineapple Beach by Florida Keys Luxury Rentals

Pineapple Beach by Florida Keys Luxury Rentals
Islamorada
Pineapple Beach by Florida Keys Luxury Rentals
Save an average of 15% on thousands of hotels when you're signed in

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
€266
14 Oct - 15 Oct
includes taxes & fees
Cheeca Lodge & Spa
The Islands of Islamorada

The Islands of Islamorada

82779 Old Hwy Islamorada FL
€585
14 Oct - 15 Oct
includes taxes & fees
The Islands of Islamorada
Still don't see what you're looking for?
See all properties in Windley Key.
You can also use these popular filters to refine your search.
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

8/10 Good
"Hallways quite loud in the mornings by staff, like they forget people are on vacation and sleeping. Pool itself is nice. Sand is very rocky so must wear shoes."
Kristen 4-night trip
Posted 4 hours ago
Amara Cay Resort
Baker's Cay Resort Key Largo, Curio Collection by Hilton

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

10/10 Excellent
"I loved the staff, management has done a great job! The food, the views, amazing!"
Idian 1-night trip
Posted 1 day ago
Baker's Cay Resort Key Largo, Curio Collection by Hilton
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

Explore a world of travel with Expedia