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.

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

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

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

8 Oct - 9 Oct

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

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.

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 resort with a pool, beach, and ocean view.

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

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

Islamorada

Liosbel

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

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

4. Drop Anchor

Islamorada

Payman

AU$270

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

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

5. The Ocean View Inn & Pub

Islamorada

Maria

AU$301

includes taxes & fees

6 Oct - 7 Oct

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

Leihla

AU$310

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 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.

7. La Jolla Resort

Matecumbe

Kayla

AU$197

includes taxes & fees

6 Oct - 7 Oct

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

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

8. Hampton Inn Key Largo Manatee Bay

Key Largo

Cory

AU$210

includes taxes & fees

20 Oct - 21 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 hotel room with a large bed, a television, a dining area with chairs, a table, and a view of the ocean.

9. Cheeca Lodge & Spa

Matecumbe

RAIBEL

AU$371

includes taxes & fees

19 Oct - 20 Oct

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

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.

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

10. Waterside Suites & Marina

Key Largo

Ysabella

AU$221

includes taxes & fees

7 Oct - 8 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 tree with string lights, a wooden bench, and a building in the background.

11. Drift Hotel

Key Largo

kelly

AU$169

includes taxes & fees

27 Oct - 28 Oct

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

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

12. Rock Reef Resort

Rock Harbor

Tia

AU$164

includes taxes & fees

8 Oct - 9 Oct

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

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

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

13. Lime Tree Bay Resort

Long Key

Michael

AU$252

includes taxes & fees

7 Oct - 8 Oct

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

A modern kitchen with wooden cabinets, a central island with stools, and a ceiling fan.

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.

14. Dolphin Point Villas

Key Largo

Ernest

AU$221

includes taxes & fees

12 Oct - 13 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 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.

An aerial view of a resort with a swimming pool, palm trees, and a dock.

15. Amara Cay Resort

Matecumbe

Danielle

AU$340

includes taxes & fees

20 Oct - 21 Oct

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

A waterfront pier with wooden posts and a wooden walkway 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.

16. Sunset Cove Beach Resort

Key Largo

Payton

AU$189

includes taxes & fees

12 Oct - 13 Oct

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

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.

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

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

Key Largo

Omar Ahmad

AU$206

includes taxes & fees

6 Oct - 7 Oct

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

A wooden pier leading to a beach with palm trees and a row of beach huts.

18. Islander Resort

Matecumbe

Steven

AU$540

includes taxes & fees

27 Oct - 28 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.

19. Bayside Inn Key Largo

Key Largo

Lwigy

AU$191

includes taxes & fees

6 Oct - 7 Oct

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

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

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

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

20. Seafarer Key Largo

Rock Harbor

ANDREW

AU$160

includes taxes & fees

8 Oct - 9 Oct

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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

Top Windley Key Hotel Reviews

Recent Reviews in Windley Key

Cheeca Lodge & Spa

10/10 Excellent

"Really a nice place. Overall the Keys are an older area with many hotels/resorts showing signs of deferred maintenance. This place was a true 5 Star. Staff is/are unbelievable. 100% recommend."

Waterside Suites & Marina

10/10 Excellent

"Clean and affordable to say the least Located closely to many restaurants and stores for essentials"

Lime Tree Bay Resort

10/10 Excellent

"Such a beautiful stay! We enjoyed access to kayaks and bikes. Staff were very helpful."

Bayside Inn Key Largo

10/10 Excellent

"Exactly the experience we wanted. Great views, great location, fishing off the dock."

Rock Reef Resort

10/10 Excellent

"The staff is amazing"

Coconut Cove Resort and Marina

10/10 Excellent

"Amazing gym, really cool pool with waterfall, beautiful view of the sunrise on a small beach. Overall was super nice."

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!!!!"

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

9/10 Wonderful! (753 reviews)

Rock Reef Resort

97850 Overseas Hwy Key Largo FL

AU$164

8 Oct - 9 Oct

includes taxes & fees

9.2/10 Wonderful! (1,187 reviews)

Sunset Cove Beach Resort

MM 99.5 Key Largo FL

AU$189

12 Oct - 13 Oct

includes taxes & fees

Hampton Inn Key Largo Manatee Bay

102400 Overseas Hwy Key Largo FL

AU$210

20 Oct - 21 Oct

includes taxes & fees

8.8/10 Excellent! (1,095 reviews)

Creekside Inn

90611 Old Highway Tavernier FL

AU$226

18 Oct - 19 Oct

includes taxes & fees

7.8/10 Good! (1,022 reviews)

Explore a world of travel with Expedia

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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. Chesapeake Beach Resort

7. La Jolla Resort

8. Hampton Inn Key Largo Manatee Bay

9. Cheeca Lodge & Spa

10. Waterside Suites & Marina

11. Drift Hotel

12. Rock Reef Resort

13. Lime Tree Bay Resort

14. Dolphin Point Villas

15. Amara Cay Resort

16. Sunset Cove Beach Resort

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

18. Islander Resort

19. Bayside Inn Key Largo

20. Seafarer Key Largo

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

Cheeca Lodge & Spa

Waterside Suites & Marina

Lime Tree Bay Resort

Bayside Inn Key Largo

Rock Reef Resort

Coconut Cove Resort and Marina

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

The Pelican Key Largo Cottages

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

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