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

Windley Key 4 Stars Hotels

  • 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
Sep 26 - Sep 27
Tomorrow
Sep 27 - Sep 28
Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11

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

1. Reefhouse Resort & Marina

Reefhouse Resort & Marina
Key Largo
United States
Susan
NT$6,319
NT$8,380 total
includes taxes & fees
Sep 27 - Sep 28
Reefhouse Resort & Marina
A wooden deck with a view of the ocean and a palm tree.
A hammock on a sandy beach with a view of the sea and a tree overhead.
A spacious interior with a high ceiling, large windows, and a central chandelier.
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.

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
Milagros
NT$8,348
NT$11,146 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 resort pool with palm trees, beach chairs, and umbrellas.
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
MICHAEL
NT$4,909
NT$7,844 total
includes taxes & fees
Sep 30 - Oct 1
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.
An outdoor dining area with round tables and chairs, a thatched roof, and a view of the sea.
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
Canada
Eslita
NT$6,580
NT$9,724 total
includes taxes & fees
Oct 13 - Oct 14
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 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.

5. Islander Resort

Islander Resort
Matecumbe
United States
John
NT$6,923
NT$10,116 total
includes taxes & fees
Sep 29 - Sep 30
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
Tania
NT$8,352
NT$11,146 total
includes taxes & fees
Oct 11 - Oct 12
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 with colorful buildings, kayaks, and lounge chairs.
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
La Siesta Resort & Villas
A beach with palm trees, lounge chairs, and a thatched-roof structure.
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.
A wooden deck with a thatched-roof structure, a sign indicating no swimming, and a clear view of the ocean.

8. Condo in the Keys

Condo in the Keys
Tavernier
United States
Angela
Condo in the Keys
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
NT$4,743
NT$7,663 total
Sep 29 - Sep 30
includes taxes & fees
9.2/10 Wonderful! (1,456 reviews)
Cheeca Lodge & Spa
The Islands of Islamorada

The Islands of Islamorada

82779 Old Hwy Islamorada FL
NT$13,147
NT$16,803 total
Oct 1 - Oct 2
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

Islander Resort

Islander Resort

8/10 Good
"I liked the fact that our rear outside seating area was quite private because of the trees and bushes growing around the property. Very peaceful and also just a couple of minutes walk from the sea."
norman 4-night trip
Posted 12 hours ago
Islander Resort

Explore a world of travel with Expedia