Windley Key Holiday Rentals, Islamorada: Private House Rentals

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 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.

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

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

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

Islamorada

Liosbel

5.593.909 ₫

8.194.088 ₫ total

includes taxes & fees

19 Oct - 20 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.

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

2. Fisher Inn Resort & Marina

Islamorada

Siobhan

3.954.987 ₫

5.297.543 ₫ total

includes taxes & fees

8 Oct - 9 Oct

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.

3. Coconut Cove Resort and Marina

Islamorada

Hailey Ritch and Patrick

3.872.063 ₫

4.356.070 ₫ total

includes taxes & fees

7 Oct - 8 Oct

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 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.

4. Drop Anchor

Islamorada

Payman

3.354.629 ₫

4.683.503 ₫ total

includes taxes & fees

8 Oct - 9 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 bathroom with a sink, toilet, and shower. There is a mirror above the sink and a shelf with towels.

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.

5. The Ocean View Inn & Pub

Islamorada

Maria

4.841.378 ₫

5.446.355 ₫ total

includes taxes & fees

18 Oct - 19 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 hotel room with a large bed, a television, a dining area with chairs, a table, and a view of the ocean.

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

6. Cheeca Lodge & Spa

Matecumbe

RAIBEL

4.912.866 ₫

7.427.916 ₫ total

includes taxes & fees

13 Oct - 14 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 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.

7. Islander Resort

Matecumbe

Steven

7.439.483 ₫

10.270.099 ₫ total

includes taxes & fees

27 Oct - 28 Oct

A dining area with tables set for two, overlooking a beach with palm trees and a sunset view.

A beach with thatched umbrellas, palm trees, and blue lounge chairs.

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

A spacious living room with large windows, comfortable seating, and decorative plants.

8. Reefhouse Resort & Marina

Key Largo

Manny

5.692.686 ₫

7.444.162 ₫ total

includes taxes & fees

7 Oct - 8 Oct

A beach with palm trees and lounge chairs.

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.

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

9. Chesapeake Beach Resort

Matecumbe

Leihla

3.925.336 ₫

5.877.771 ₫ total

includes taxes & fees

14 Oct - 15 Oct

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

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.

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

10. Hampton Inn Key Largo Manatee Bay

Key Largo

Cory

3.367.783 ₫

3.788.756 ₫ total

includes taxes & fees

20 Oct - 21 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.

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.

11. Amara Cay Resort

Matecumbe

Danielle

4.018.023 ₫

6.421.216 ₫ total

includes taxes & fees

18 Oct - 19 Oct

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

A garden with various trees and a gravel path.

A balcony with a view of the sea, a beach, and a thatched hut.

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

12. Sunset Cove Beach Resort

Key Largo

Payton

3.041.298 ₫

3.421.590 ₫ total

includes taxes & fees

12 Oct - 13 Oct

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 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.

A spacious dining area with high ceilings, wicker furniture, and large windows.

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

Key Largo

Micheal

7.284.039 ₫

9.627.593 ₫ total

includes taxes & fees

20 Oct - 21 Oct

An aerial view of a resort with a large pool, palm trees, and a beach.

A pool area with lounge chairs and umbrellas, a clear sky, and palm trees.

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.

14. Playa Largo Resort & Spa, Autograph Collection

Rock Harbor

Tania

6.836.422 ₫

9.124.024 ₫ total

includes taxes & fees

19 Oct - 20 Oct

A balcony with wicker chairs and a small table overlooking a marina with boats and palm trees.

A modern kitchen with a curved island, stainless steel appliances, and a menu board.

A pool area with lounge chairs, a thatched umbrella, and a marina in the background.

A marina with multiple boats docked, surrounded by palm trees and buildings.

15. Courtyard by Marriott Key Largo

Key Largo

Anna

3.953.687 ₫

4.447.898 ₫ total

includes taxes & fees

11 Oct - 12 Oct

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

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

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

A beach with palm trees, a sandy path, and a building with a balcony.

16. Bayside Inn Key Largo

Key Largo

Lwigy

2.804.753 ₫

3.805.197 ₫ total

includes taxes & fees

7 Oct - 8 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.

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

17. Waterside Suites & Marina

Key Largo

Ysabella

3.185.565 ₫

4.314.841 ₫ total

includes taxes & fees

7 Oct - 8 Oct

A balcony with two white chairs overlooking a marina with boats, a building with a green roof, and palm trees.

A rectangular swimming pool with a tiled deck, surrounded by lounge chairs and thatched umbrellas.

A bar area with a thatched roof, wooden furniture, and a variety of bottles.

A restaurant with indoor seating, a long counter, and large windows.

18. Holiday Inn Key Largo by IHG

Key Largo

suany

4.522.956 ₫

5.088.325 ₫ total

includes taxes & fees

11 Oct - 12 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

2.550.011 ₫

3.693.032 ₫ total

includes taxes & fees

14 Oct - 15 Oct

A view through a window with metal bars, featuring a beach with palm trees, a thatched umbrella, and a wooden dock.

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

A tropical resort with a paved pathway leading to a building, surrounded by palm trees and lush greenery.

A beach with kayaks lined up near the water's edge, palm trees, and lounge chairs.

20. Kona Kai Resort and Gallery - Adults Only

Rock Harbor

Karen

4.175.936 ₫

5.429.139 ₫ total

includes taxes & fees

7 Oct - 8 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 great outdoors at Windley Key Fossil Reef Geological State Park and enjoy the beautiful sunsets during your trip to Islamorada. Wander through the seaside and beautiful beaches in this family-friendly area.

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

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

10/10 Excellent

"Clean, comfortable rooms. On site amenities were fantastic!"

Amara Cay Resort

10/10 Excellent

"Very clean resort. The pool was fabulous. The tiki bar was great. Stall friendly and helpful. Truly enjoyed my stay!"

Waterside Suites & Marina

10/10 Excellent

"Great place. We stay here every year"

Cheeca Lodge & Spa

10/10 Excellent

"Staff is very helpful, rooms are clean, and there is a lot to do on the property!"

Islander Resort

10/10 Excellent

"Muy buenas condiciones , recomendado para una experiencia inolvidable"

The Pelican Key Largo Cottages

10/10 Excellent

"All together great"

Reefhouse Resort & Marina

10/10 Excellent

"Excellent place"

Lime Tree Bay Resort

10/10 Excellent

"It’s always good to visit this resort so many things to do"

Bayside Inn Key Largo

10/10 Excellent

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

More cheap stays in Windley Key

Rock Reef Resort

97850 Overseas Hwy Key Largo FL

2.408.344 ₫

2.709.388 ₫ total

20 Oct - 21 Oct

includes taxes & fees

9.2/10 Wonderful! (1,187 reviews)

Breezy Palms Resort

80015 Overseas Highway Islamorada FL

2.125.010 ₫

2.805.533 ₫ total

7 Oct - 8 Oct

includes taxes & fees

9/10 Wonderful! (755 reviews)

The Pelican Key Largo Cottages

99340 Overseas Highway Key Largo FL

2.623.038 ₫

2.950.917 ₫ total

8 Oct - 9 Oct

includes taxes & fees

9/10 Wonderful! (1,003 reviews)

Sunset Cove Beach Resort

MM 99.5 Key Largo FL

3.041.298 ₫

3.421.590 ₫ total

12 Oct - 13 Oct

includes taxes & fees

Hampton Inn Key Largo Manatee Bay

102400 Overseas Hwy Key Largo FL

3.367.783 ₫

3.788.756 ₫ total

20 Oct - 21 Oct

includes taxes & fees

8.8/10 Excellent! (1,098 reviews)

Creekside Inn

90611 Old Highway Tavernier FL

3.700.766 ₫

4.163.459 ₫ total

11 Oct - 12 Oct

includes taxes & fees

7.8/10 Good! (1,022 reviews)

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Find hotels in Windley Key, FL from 2.709.388 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Windley Key

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Windley Key hotels

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

2. Fisher Inn Resort & Marina

3. Coconut Cove Resort and Marina

4. Drop Anchor

5. The Ocean View Inn & Pub

6. Cheeca Lodge & Spa

7. Islander Resort

8. Reefhouse Resort & Marina

9. Chesapeake Beach Resort

10. Hampton Inn Key Largo Manatee Bay

11. Amara Cay Resort

12. Sunset Cove Beach Resort

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

14. Playa Largo Resort & Spa, Autograph Collection

15. Courtyard by Marriott Key Largo

16. Bayside Inn Key Largo

17. Waterside Suites & Marina

18. Holiday Inn Key Largo by IHG

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

20. Kona Kai Resort and Gallery - Adults Only

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

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

Amara Cay Resort

Waterside Suites & Marina

Cheeca Lodge & Spa

Islander Resort

The Pelican Key Largo Cottages

Reefhouse Resort & Marina

Lime Tree Bay Resort

Bayside Inn Key Largo

More cheap stays in Windley Key

Rock Reef Resort

Breezy Palms Resort

The Pelican Key Largo Cottages

Sunset Cove Beach Resort

Hampton Inn Key Largo Manatee Bay

Creekside Inn

Explore a world of travel with Expedia

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