Windley Key Hotel & Accommodation Deals 2026 from AU$142 - Compare prices by date

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

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

Go beyond your typical stay in Windley Key

Pet friendly

Apartment

Villa

Apart hotel

Spa

Condo

Pool

Spa pool

Family friendly

Resort

Houseboat

Waterpark

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

Our top choices for Windley Key hotels

A clear blue pool surrounded by palm trees and a thatched-roof structure, with a view of the ocean in the background.

A resort with thatched-roof structures, palm trees, and a sandy beach area.

A wooden deck with a thatched roof structure, wooden chairs, and a table, overlooking a tropical landscape with palm trees and a clear sky.

A beach with palm trees, a thatched-roof hut, and lounge chairs.

1. Coconut Cove Resort and Marina

Islamorada

Hailey Ritch and Patrick

AU$222

includes taxes & fees

5 Oct - 6 Oct

A beachfront hotel with a pool, beach chairs, and a view of the ocean at sunset.

A hotel room with two beds, a TV, a desk with a chair, and a balcony with a view of greenery.

A man standing next to a boat on a wooden dock with a chain barrier, palm trees, and a building in the background.

Two people relaxing on sun loungers by a poolside with a view of the ocean and palm trees in the background.

2. Fisher Inn Resort & Marina

Islamorada

Siobhan

AU$252

includes taxes & fees

12 Oct - 13 Oct

A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.

A beach with palm trees, a clear blue sky, and a calm sea.

A coastal resort with a beach, a swimming pool, and multiple buildings.

An outdoor dining area with round tables and chairs, a thatched roof, and a view of the sea.

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

Islamorada

Eslita

AU$453

includes taxes & fees

18 Oct - 19 Oct

A beachside patio with white furniture, palm trees, and a thatched umbrella.

A deck with white lounge chairs and a bench, overlooking a beach with palm trees and a thatched roof structure.

A wooden boardwalk leading to a building with a brick wall and a white roof.

A beach with palm trees, a thatched umbrella, and lounge chairs.

4. Drop Anchor

Islamorada

Payman

AU$263

includes taxes & fees

6 Oct - 7 Oct

A bedroom with a large bed, a sliding glass door to a balcony, a wooden cabinet, and a kitchen area with a microwave.

A hotel room with two beds, each with a different patterned bedspread, a nightstand with a lamp, framed artwork on the wall, and an air conditioning unit.

A bathroom with a sink, toilet, and shower. There is a mirror above the sink and a shelf with towels.

A swimming pool with a 5 ft depth marker, surrounded by palm trees and a white picket fence.

5. The Ocean View Inn & Pub

Islamorada

Maria

AU$301

includes taxes & fees

6 Oct - 7 Oct

A beach with palm trees, lounge chairs, and a clear view of the ocean.

A resort with a thatched-roof structure, palm trees, and lounge chairs on a sandy beach.

A tropical garden with palm trees, various colorful plants, and a seating area with chairs.

A clear blue pool with lounge chairs and palm trees.

6. Hampton Inn Key Largo Manatee Bay

Key Largo

Cory

AU$184

includes taxes & fees

14 Oct - 15 Oct

A beach with palm trees and lounge chairs.

A hotel room with a large bed, a ceiling fan, a nightstand with a lamp, and a view of the beach through the window.

A balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.

A waterfront hotel with multiple floors, palm trees, and a calm reflective pool.

7. Chesapeake Beach Resort

Matecumbe

Leihla

AU$310

includes taxes & fees

5 Oct - 6 Oct

A beach with thatched umbrellas, wooden chairs, and a wooden pier extending into the water.

A view through a door of a tropical outdoor area with a pathway leading to a beach, palm trees, and a clear sky.

A garden with various trees and a gravel path.

A waterfront pier with wooden posts and a wooden walkway extending into the water.

8. Sunset Cove Beach Resort

Key Largo

Payton

AU$181

includes taxes & fees

6 Oct - 7 Oct

A beach with two thatched umbrellas, three sun loungers, and a view of the sea with boats.

A beach with a row of palm trees, a rocky breakwater, and boats on the water.

A marina with docks, lounge chairs, and a clear view of the water.

A waterfront property with a large building, a dock, lounge chairs, and a thatched-roof area.

9. Dolphin Point Villas

Key Largo

Ernest

AU$227

includes taxes & fees

8 Oct - 9 Oct

A beach hut with a thatched roof, surrounded by lounge chairs and a picnic table, overlooking a calm sea.

A wooden interior with a large window overlooking a beach with a thatched umbrella and lounge chairs.

A pool area with a view of the ocean, surrounded by palm trees and a clear sky.

A wooden dock with a boat docked at the pier, a thatched umbrella, and calm water.

10. Rock Reef Resort

Rock Harbor

Tia

AU$164

includes taxes & fees

8 Oct - 9 Oct

A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.

A beachfront property with a staircase leading to a light blue building, palm trees, and a clear view of the ocean.

A bedroom with a bed, two chairs, a sofa, a TV, and a large window with a view of the ocean.

A beachfront property with a white building, a balcony with a white railing, and palm trees.

11. La Jolla Resort

Matecumbe

Kayla

AU$197

includes taxes & fees

6 Oct - 7 Oct

A balcony with a view of the sea, a table, and two chairs.

A marina with boats docked along a waterfront, surrounded by buildings and palm trees.

A bedroom with a bed, a TV mounted on the wall, a window with blinds, and a chandelier.

12. Waterside Suites & Marina

Key Largo

Ysabella

AU$221

includes taxes & fees

7 Oct - 8 Oct

A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.

A tropical resort with a swimming pool, palm trees, and a waterfall.

A spacious lobby with a seating area, a bar, and a large window providing a view of the outdoors.

A bar area with a thatched roof, wooden chairs, and a view of the ocean.

13. Cheeca Lodge & Spa

Matecumbe

RAIBEL

AU$385

includes taxes & fees

21 Oct - 22 Oct

A beach with lounge chairs and a blue umbrella, a pier with boats, and a mural of wings on a wall.

A beach with lounge chairs, kayaks, and a wooden pier.

A modern living room with a dark brown sofa, a coffee table, and a blue lamp. There is a kitchen area with a microwave and a coffee machine. A painting of a beach scene is on the wall.

A modern living room with a sofa, a glass coffee table, a TV, and a sliding door leading to a bedroom.

14. Drift Hotel

Key Largo

kelly

AU$170

includes taxes & fees

29 Oct - 30 Oct

Two hands holding wine glasses with a beach and ocean view in the background.

An aerial view of a resort with a swimming pool, beach area, and dock.

A bed with white and turquoise pillows, a bottle of champagne, and two glasses on a round table.

15. Bayside Inn Key Largo

Key Largo

Lwigy

AU$193

includes taxes & fees

5 Oct - 6 Oct

A white building with a purple door, surrounded by palm trees.

A beach with a boat docked near the shore, a thatched-roof structure, and palm trees.

A bedroom with a bed, nightstands, a bench, a TV, a painting, and a view through a glass door.

A beachside seating area with two white Adirondack chairs and a small table under a thatched roof structure.

16. Amoray Dive Resort

Key Largo

AU$175

includes taxes & fees

5 Oct - 6 Oct

A resort with a swimming pool, lounge chairs, and palm trees.

A spacious living area with a large island, wooden furniture, and a ceiling fan.

A bedroom with a large bed, a ceiling fan, a TV on the wall, and a view of the beach through a window.

17. Lime Tree Bay Resort

Long Key

Michael

AU$252

includes taxes & fees

6 Oct - 7 Oct

A beachside lounge with two blue umbrellas, a hammock, and lounge chairs.

A beach scene with colorful Adirondack chairs, a blue umbrella, and a view of the ocean.

A sunset over a calm body of water with a dock and lounge chairs.

A pathway lined with palm trees and a speed limit sign of 5 MPH.

18. Seafarer Key Largo

Rock Harbor

ANDREW

AU$169

includes taxes & fees

5 Oct - 6 Oct

A beach with hammocks under palm trees, a sandy beach, and a clear blue sky.

A resort with a pool, multiple buildings, and a waterfront view.

A modern kitchen with a built-in stove, a large island, and a view to a balcony with outdoor seating.

A paved pathway leading to a body of water, surrounded by lush greenery and palm trees.

19. Dove Creek Resort & Marina, Trademark Collection by Wyndham

Key Largo

Omar Ahmad

AU$206

includes taxes & fees

5 Oct - 6 Oct

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.

20. Amara Cay Resort

Matecumbe

Danielle

AU$340

includes taxes & fees

20 Oct - 21 Oct

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Windley Key attractions

Windley Key Fossil Reef Geological State Park

8.8/10 (184 reviews)

Explore the fossilized reef of a former quarry in this island park, as you learn about the history and ecology from the interpretive trails.

See properties

Hog Heaven

After visiting Hog Heaven, make a plan to see the other sights and activities in Islamorada. Discover the beautiful sunsets in this relaxing area or enjoy its fishing spots.

See properties

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

Top Windley Key Hotel Reviews

Recent Reviews in Windley Key

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

10/10 Excellent

"I liked everything, you have everything in the resort, restaurant, pizzeria, ice cream shop, very good service on the beach, pool. I hope to return very soon."

Lime Tree Bay Resort

8/10 Good

"Excelente"

Hampton Inn Key Largo Manatee Bay

10/10 Excellent

"Simply warm and friendly"

Cheeca Lodge & Spa

10/10 Excellent

"Clean"

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

8/10 Good

"Due to low occupancy, the restaurant was closed. They also changed the breakfast arrangement. Instead of being able to choose something from the menu, we were asked to use the buffet, which was expensive and not very good. We received a brochure with all the programs, menus, and other information, but nobody informed us about these changes. This was very confusing and disappointing."

The Pelican Key Largo Cottages

10/10 Excellent

"Excellent property, great location, clean rooms and very cozy. Very peaceful too! The front desk lady was awesome!!!!"

Bayside Inn Key Largo

10/10 Excellent

"Always my to go place in the Keys! Very friendly staff. Clean rooms."

Drop Anchor

10/10 Excellent

"Exceeded all my expectations, definitely going back. Highly recommend"

More cheap accommodation in Windley Key

The Pelican Key Largo Cottages

99340 Overseas Highway Key Largo FL

AU$142

6 Oct - 7 Oct

includes taxes & fees

9/10 Wonderful! (1,002 reviews)

Breezy Palms Resort

80015 Overseas Highway Islamorada FL

AU$155

6 Oct - 7 Oct

includes taxes & fees

Rock Reef Resort

97850 Overseas Hwy Key Largo FL

AU$164

8 Oct - 9 Oct

includes taxes & fees

Sunset Cove Beach Resort

MM 99.5 Key Largo FL

AU$181

6 Oct - 7 Oct

includes taxes & fees

Hampton Inn Key Largo Manatee Bay

102400 Overseas Hwy Key Largo FL

AU$184

14 Oct - 15 Oct

includes taxes & fees

8.8/10 Excellent! (1,094 reviews)

Creekside Inn

90611 Old Highway Tavernier FL

AU$230

11 Oct - 12 Oct

includes taxes & fees

7.8/10 Good! (1,022 reviews)

Explore a world of travel with Expedia

Book Hotels in Windley Key on Expedia.com

Search Windley Key hotels

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Windley Key

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for Windley Key hotels

1. Coconut Cove Resort and Marina

2. Fisher Inn Resort & Marina

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

4. Drop Anchor

5. The Ocean View Inn & Pub

6. Hampton Inn Key Largo Manatee Bay

7. Chesapeake Beach Resort

8. Sunset Cove Beach Resort

9. Dolphin Point Villas

10. Rock Reef Resort

11. La Jolla Resort

12. Waterside Suites & Marina

13. Cheeca Lodge & Spa

14. Drift Hotel

15. Bayside Inn Key Largo

16. Amoray Dive Resort

17. Lime Tree Bay Resort

18. Seafarer Key Largo

19. Dove Creek Resort & Marina, Trademark Collection by Wyndham

20. Amara Cay Resort

Stay near popular Windley Key attractions

Windley Key Fossil Reef Geological State Park

Hog Heaven

Learn more about Windley Key

Top Windley Key Hotel Reviews

Recent Reviews in Windley Key

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

Lime Tree Bay Resort

Hampton Inn Key Largo Manatee Bay

Cheeca Lodge & Spa

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

The Pelican Key Largo Cottages

Bayside Inn Key Largo

Drop Anchor

More cheap accommodation in Windley Key

The Pelican Key Largo Cottages

Breezy Palms Resort

Rock Reef Resort

Sunset Cove Beach Resort

Hampton Inn Key Largo Manatee Bay

Creekside Inn

Explore a world of travel with Expedia

Go further with the Expedia app