Windley Key Hotel & Accommodation Deals 2026 from AU$145 - 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

Condo

Spa

Apart hotel

Spa pool

Pool

Houseboat

Resort

Family friendly

Waterpark

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Windley Key hotels

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 covered outdoor seating area with wicker chairs and a table, overlooking a beach with palm trees and a wooden deck.

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

1. Fisher Inn Resort & Marina

Islamorada

MARC

AU$206

includes taxes & fees

20 Sept - 21 Sept

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.

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

Islamorada

Ana

AU$430

includes taxes & fees

30 Aug - 31 Aug

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

A pool area with lounge chairs and a sign indicating a drop-off zone.

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

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

3. Drop Anchor

Islamorada

Marianela

AU$242

includes taxes & fees

24 Aug - 25 Aug

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

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.

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

4. Coconut Cove Resort and Marina

Islamorada

Lisa C

AU$224

includes taxes & fees

30 Aug - 31 Aug

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

A bedroom with a bed, a nightstand, a chair, and a door.

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

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

5. The Ocean View Inn & Pub

Islamorada

Patrice

AU$294

includes taxes & fees

24 Aug - 25 Aug

A beach with palm trees and lounge chairs.

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

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.

6. Chesapeake Beach Resort

Matecumbe

Rey

AU$318

includes taxes & fees

30 Aug - 31 Aug

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

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

A hotel room with a large bed, a television, a dining area with chairs, a table, and a view of the ocean.

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

7. Cheeca Lodge & Spa

Matecumbe

Jessica

AU$338

includes taxes & fees

2 Sept - 3 Sept

A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

A pool area with a white fence, a lifebuoy, and palm trees in the background.

A row of floating cottages with balconies and outdoor seating, docked along a waterway.

A kitchen with white cabinets, a microwave, a stove, and a refrigerator.

8. Treasure Harbor

Islamorada

Molly

AU$381

includes taxes & fees

23 Aug - 24 Aug

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

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

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

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

9. La Jolla Resort

Matecumbe

adrian

AU$228

includes taxes & fees

27 Aug - 28 Aug

A balcony with a view of a beach, a pool, and a thatched-roof structure.

An aerial view of a marina with docked boats, a building with balconies, and a beach area.

A pool area with lounge chairs and umbrellas, surrounded by palm trees and buildings.

A pier with boats docked, a thatched-roof structure, and signs indicating tours and rentals.

10. Hadley Resort and Marina

Matecumbe

RAIBEL

AU$219

includes taxes & fees

7 Sept - 8 Sept

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.

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.

A beach with palm trees, a dock, and lounge chairs.

11. Amara Cay Resort

Matecumbe

David A

AU$350

includes taxes & fees

25 Aug - 26 Aug

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 paved pathway leading to a beach with palm trees and a view of the ocean.

12. Islander Resort

Matecumbe

Chris

AU$433

includes taxes & fees

1 Sept - 2 Sept

A beach with rows of sun loungers and palm trees.

A marina with a boat docked at a wooden pier, surrounded by palm trees and buildings.

A clear blue swimming pool with a metal railing, surrounded by palm trees and a view of the ocean.

Three Adirondack chairs facing a sunset over a body of water.

13. Ragged Edge Resort & Marina

Islamorada

Katarzyna

AU$200

includes taxes & fees

8 Sept - 9 Sept

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

A tree with string lights, a wooden bench, and a building in the background.

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

14. Drift Hotel

Key Largo

Sheily

AU$157

includes taxes & fees

24 Aug - 25 Aug

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

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

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

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

15. Rock Reef Resort

Rock Harbor

manuel

AU$153

includes taxes & fees

25 Aug - 26 Aug

A wooden dock extending over calm turquoise water, lined with white railings and palm trees.

A wooden sign with the name 'Creekside' above a white pergola entrance.

A hallway with a tiled floor, a painting on the wall, a lamp, and a view of a pool area.

A waterfront patio with outdoor seating, a yellow umbrella, and a view of the water.

16. Creekside Inn

Tavernier

Cristy

AU$212

includes taxes & fees

23 Aug - 24 Aug

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

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

A hotel room with a bed, a TV, a sofa, and a balcony with a view.

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

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

Key Largo

Mae L

AU$185

includes taxes & fees

1 Sept - 2 Sept

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.

A swimming pool with lounge chairs and umbrellas, a fenced area, and a building with a door.

18. Waterside Suites & Marina

Key Largo

Jennifer

AU$214

includes taxes & fees

26 Aug - 27 Aug

A beachfront property with a pool, palm trees, and a thatched-roof structure.

A pathway leading to a beach with tropical plants and flowers.

A wooden pier leading to docked boats, with a covered area and a calm water body in the background.

A beach pathway lined with palm trees leading to a seating area with a view of the ocean.

19. Coconut Palm Inn

Tavernier

judith

AU$352

includes taxes & fees

23 Aug - 24 Aug

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.

20. Hampton Inn Key Largo Manatee Bay

Key Largo

Susanna

AU$206

includes taxes & fees

31 Aug - 1 Sept

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

An archaeological site with stone structures and metal machinery.

Top Windley Key Hotel Reviews

Recent Reviews in Windley Key

Amara Cay Resort

8/10 Good

"The hotel was great, and the room was very spacious for a two-queen-bed setup. Our only disappointment was that we didn’t realize the property didn’t have a true beach with direct ocean access. Since it was our first time visiting the Keys, we weren’t quite sure what to expect, so it would be helpful if this was communicated more clearly in the hotel’s description. Other than that, we had a wonderful stay and really enjoyed our time there."

Cheeca Lodge & Spa

10/10 Excellent

"Took my family here. Staff is so friendly. Everything was clean and restaurants were good. We can wait to come back."

Lime Tree Bay Resort

10/10 Excellent

"Great place, very nice staff!"

Islander Resort

10/10 Excellent

"Gorgeous and relaxing. We had a wonderful time! Staff were super friendly."

Fisher Inn Resort & Marina

10/10 Excellent

"Ok."

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

8/10 Good

"Shuttle driver was driving while in personal FaceTime call. Did not move to help with van door which was hard to close. The resort is beautiful and we really enjoyed the amenities."

Hampton Inn Key Largo Manatee Bay

10/10 Excellent

"Superb location. Great Tiki bar!"

Waterside Suites & Marina

10/10 Excellent

"Great one night stay. Property was clean and convenient!"

Marina Del Mar Resort and Marina

8/10 Good

"Todo excelente y económico"

More cheap accommodation in Windley Key

The Pelican Key Largo Cottages

99340 Overseas Highway Key Largo FL

AU$145

25 Aug - 26 Aug

includes taxes & fees

Drift Hotel

95320 Overseas Hwy Key Largo FL

AU$157

24 Aug - 25 Aug

includes taxes & fees

9/10 Wonderful! (1,008 reviews)

Breezy Palms Resort

80015 Overseas Highway Islamorada FL

AU$184

1 Sept - 2 Sept

includes taxes & fees

8.8/10 Excellent! (728 reviews)

Hampton Inn Key Largo Manatee Bay

102400 Overseas Hwy Key Largo FL

AU$206

31 Aug - 1 Sept

includes taxes & fees

8.8/10 Excellent! (1,065 reviews)

Creekside Inn

90611 Old Highway Tavernier FL

AU$212

23 Aug - 24 Aug

includes taxes & fees

7.8/10 Good! (1,015 reviews)

Marina Del Mar Resort and Marina

527 Caribbean Drive Key Largo FL

AU$259

20 Sept - 21 Sept

includes taxes & fees

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. Fisher Inn Resort & Marina

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

3. Drop Anchor

4. Coconut Cove Resort and Marina

5. The Ocean View Inn & Pub

6. Chesapeake Beach Resort

7. Cheeca Lodge & Spa

8. Treasure Harbor

9. La Jolla Resort

10. Hadley Resort and Marina

11. Amara Cay Resort

12. Islander Resort

13. Ragged Edge Resort & Marina

14. Drift Hotel

15. Rock Reef Resort

16. Creekside Inn

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

18. Waterside Suites & Marina

19. Coconut Palm Inn

20. Hampton Inn Key Largo Manatee Bay

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

Amara Cay Resort

Cheeca Lodge & Spa

Lime Tree Bay Resort

Islander Resort

Fisher Inn Resort & Marina

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

Hampton Inn Key Largo Manatee Bay

Waterside Suites & Marina

Marina Del Mar Resort and Marina

More cheap accommodation in Windley Key

The Pelican Key Largo Cottages

Drift Hotel

Breezy Palms Resort

Hampton Inn Key Largo Manatee Bay

Creekside Inn

Marina Del Mar Resort and Marina

Explore a world of travel with Expedia

Go further with the Expedia app