Windley Key Hotel & Accommodation Deals 2026 from AU$153 - Compare prices by date

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

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Our top choices for Windley Key hotels

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

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

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.

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.

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

A resort with a pool, beach, and ocean view.

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

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

Islamorada

Ana

AU$430

includes taxes & fees

26 Aug - 27 Aug

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

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

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

A beachside resort with thatched-roof huts, palm trees, and a sandy area with rocks and wooden chairs.

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

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 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.

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.

5. The Ocean View Inn & Pub

Islamorada

Patrice

AU$294

includes taxes & fees

3 Sept - 4 Sept

A beach with palm trees and lounge chairs.

A swimming pool with clear blue water, surrounded by a white deck and a black metal fence.

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

6. Chesapeake Beach Resort

Matecumbe

Rey

AU$318

includes taxes & fees

25 Aug - 26 Aug

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

7. Cheeca Lodge & Spa

Matecumbe

Jessica

AU$338

includes taxes & fees

3 Sept - 4 Sept

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

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

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

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

8. Treasure Harbor

Islamorada

Molly

AU$383

includes taxes & fees

21 Aug - 22 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 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.

9. La Jolla Resort

Matecumbe

adrian

AU$259

includes taxes & fees

23 Aug - 24 Aug

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

A beach scene with two yellow beach chairs and a person lying on one.

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

15 Sept - 16 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$349

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 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.

12. Islander Resort

Matecumbe

Chris

AU$433

includes taxes & fees

7 Sept - 8 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 spacious room with a high ceiling, a ceiling fan, a dining table with chairs, a sofa, and a television mounted on the wall.

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

13. Ragged Edge Resort & Marina

Islamorada

Katarzyna

AU$206

includes taxes & fees

9 Sept - 10 Sept

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

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

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

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.

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

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

A swimming pool with a rock waterfall feature and a 3 ft depth marker.

16. Creekside Inn

Tavernier

Cristy

AU$212

includes taxes & fees

24 Aug - 25 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 resort with a pool, multiple buildings, and a waterfront view.

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

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

Key Largo

Mae L

AU$185

includes taxes & fees

7 Sept - 8 Sept

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

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

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

18. Waterside Suites & Marina

Key Largo

Jennifer

AU$212

includes taxes & fees

30 Aug - 31 Aug

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

A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the water.

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

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

19. Coconut Palm Inn

Tavernier

judith

AU$354

includes taxes & fees

23 Aug - 24 Aug

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

A clear blue pool with lounge chairs and palm trees.

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

A hotel room with a kitchenette, two beds, a desk, a television, and a ceiling fan.

20. Hampton Inn Key Largo Manatee Bay

Key Largo

Susanna

AU$206

includes taxes & fees

1 Sept - 2 Sept

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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

Reefhouse Resort & Marina

10/10 Excellent

"El servicio y privacidad"

Bayside Inn Key Largo

10/10 Excellent

"Lovely staff! Beautiful place!"

Amara Cay Resort

10/10 Excellent

"Great place!"

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!"

Lime Tree Bay Resort

10/10 Excellent

"Beautiful place. Outstanding views. There were free bikes, kayaks and paddle boards available. There is a small pier and fishing is allowed. I loved the property I’ll be staying there again because is one of the best places you can go in Fl Keys."

Islander Resort

10/10 Excellent

"I decided to splurge on myself and do a night and a day at the resort and man oh man what a treat. I have been to other resorts in the Caribbean and Mexico and this space totally gives you that vibe everywhere you go! Beautiful landscaping and gardens! Rooms were huge and so well decorated! This room also had a back patio to hang out on! The long walkway to the beach and pool area is so relaxing and really sets the tone for your experience! Pool area was chill, they had a live singer out by the pool area who was really good. Tons of activities that you could engage in, basketball, mini golf, cornhole! You could even go fishing on the pier or hang out in a plethora of outdoor lounge seating. Unfortunately as is many of the areas in Islamorada, don’t expect to be swimming in the ocean, Islander Resort is the same, so much seaweed and unable for swimming, but that’s not their fault, more the environment and the way it goes in the summer months. Lobby was beautiful and catered to any need I had. Nighttime roaming and wandering around the space is chill and great resort vibes. Would def go back again in the future!"

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$156

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

7 Sept - 8 Sept

includes taxes & fees

8.8/10 Excellent! (728 reviews)

Hampton Inn Key Largo Manatee Bay

102400 Overseas Hwy Key Largo FL

AU$206

1 Sept - 2 Sept

includes taxes & fees

8.8/10 Excellent! (1,064 reviews)

Creekside Inn

90611 Old Highway Tavernier FL

AU$212

24 Aug - 25 Aug

includes taxes & fees

7.8/10 Good! (1,015 reviews)

Marina Del Mar Resort and Marina

527 Caribbean Drive Key Largo FL

AU$257

2 Sept - 3 Sept

includes taxes & fees

8.6/10 Excellent! (1,875 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. 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

Reefhouse Resort & Marina

Bayside Inn Key Largo

Amara Cay Resort

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

Hampton Inn Key Largo Manatee Bay

Lime Tree Bay Resort

Islander Resort

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