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

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

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

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

1. Fisher Inn Resort & Marina

Islamorada

Alexandra

3.062.212 ₫

4.290.693 ₫ total

includes taxes & fees

21 Sept - 22 Sept

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

2. Drop Anchor

Islamorada

Marianela

2.754.648 ₫

4.006.180 ₫ total

includes taxes & fees

13 Sept - 14 Sept

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

3. Coconut Cove Resort and Marina

Islamorada

Jasmine

3.861.782 ₫

4.344.505 ₫ total

includes taxes & fees

13 Sept - 14 Sept

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

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

4. The Ocean View Inn & Pub

Islamorada

Maria

4.828.523 ₫

5.431.894 ₫ total

includes taxes & fees

13 Sept - 14 Sept

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

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

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

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

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

Islamorada

Ana

4.748.178 ₫

7.237.084 ₫ total

includes taxes & fees

20 Sept - 21 Sept

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

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

6. Chesapeake Beach Resort

Matecumbe

Suresh

3.090.722 ₫

4.934.950 ₫ total

includes taxes & fees

16 Sept - 17 Sept

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

7. Cheeca Lodge & Spa

Matecumbe

Mian

3.861.782 ₫

6.240.017 ₫ total

includes taxes & fees

15 Sept - 16 Sept

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

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.

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

8. Creekside Inn

Tavernier

Terry

3.412.105 ₫

3.838.456 ₫ total

includes taxes & fees

20 Sept - 21 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 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.

9. Drift Hotel

Key Largo

Sheily

2.429.812 ₫

3.025.117 ₫ total

includes taxes & fees

17 Sept - 18 Sept

A beach with rows of sun loungers and palm trees.

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

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

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

10. Ragged Edge Resort & Marina

Islamorada

Marianne

2.256.810 ₫

2.538.911 ₫ total

includes taxes & fees

20 Sept - 21 Sept

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.

11. Hadley Resort and Marina

Matecumbe

RAIBEL

3.172.608 ₫

4.414.954 ₫ total

includes taxes & fees

15 Sept - 16 Sept

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.

12. Rock Reef Resort

Rock Harbor

charlotte

2.614.623 ₫

2.941.451 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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

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

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

Key Largo

Omar Ahmad

2.542.556 ₫

3.682.236 ₫ total

includes taxes & fees

20 Sept - 21 Sept

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

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.

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

14. Sunset Cove Beach Resort

Key Largo

Melissa

2.542.752 ₫

2.860.790 ₫ total

includes taxes & fees

17 Sept - 18 Sept

A multi-story hotel with balconies, palm trees, and a view of the water.

A marina with boats docked, surrounded by palm trees.

A swimming pool with lounge chairs and palm trees.

A beachside area with palm trees, a wooden bench, and a wheelchair-accessible sign.

15. Marina Del Mar Resort and Marina

Key Largo

Brenda

3.602.602 ₫

4.782.000 ₫ total

includes taxes & fees

13 Sept - 14 Sept

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 beach with a thatched hut, palm trees, and a calm sea.

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

16. Amoray Dive Resort

Key Largo

2.467.394 ₫

3.504.891 ₫ total

includes taxes & fees

13 Sept - 14 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.

A resort pool with palm trees, beach chairs, and umbrellas.

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.

17. Amara Cay Resort

Matecumbe

Amy

4.006.275 ₫

6.402.443 ₫ total

includes taxes & fees

14 Sept - 15 Sept

An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

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

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

A bar area with a wooden counter, bar stools, and potted plants.

18. Islander Resort

Matecumbe

Sonia

5.749.908 ₫

8.218.112 ₫ total

includes taxes & fees

20 Sept - 21 Sept

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

A hotel room with a large bed, a desk with a chair, a television, and a window with curtains.

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.

19. Holiday Inn Key Largo by IHG

Key Largo

suany

4.173.120 ₫

4.694.759 ₫ total

includes taxes & fees

12 Oct - 13 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 beach with palm trees and a clear view of the ocean.

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

20. Lime Tree Bay Resort

Long Key

Chadwick

2.697.533 ₫

5.237.924 ₫ total

includes taxes & fees

14 Sept - 15 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 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

Rock Reef Resort

8/10 Good

"The staff was great, the room was very clean and quiet."

Playa Largo Resort & Spa, Autograph Collection

10/10 Excellent

"Super good resorts"

Lime Tree Bay Resort

10/10 Excellent

"Overall great experience. Will book again in the future"

The Pelican Key Largo Cottages

10/10 Excellent

"This is my new go-to place to stay in Key Largo! It's clean, quaint & a good location. The view at the dock at Sunset was stunning. We had two queens & a bathroom. Our room was right behind the check in building so it was convenient to us. There also seems to be a table & chairs outside each room, I didn't know that when I booked but I was able to have my morning tea outside. Another nice feature was the in-room fridge (which was super cold), the coffee maker & the microwave. This microwave was nice! It had a USB & 3-prong plug on the front of it & when it stops running it's locked & you have to push the unlock button. If you are traveling with kids, this is a wonderful safety feature! We walked down to the docks twice on our overnight stay. There are chairs on the beach & on the dock. There were plenty of local places to eat, but I recommend C&Cs Wood Fired Pizza for their happy hour from 4-6 pm. A pizza (6 slices) & a pitcher for $10! At the Cottages, the staff were super nice. Irina & the other lady at check in were so helpful. I even asked a grounds person a question & he was helpful too. I don't care about super fancy. I care about CLEAN, a great view & beautiful surrounding. It's all of this & more!"

Islander Resort

8/10 Good

"Good location. nice clean rooms. bed was very firm. pool tends to get very warm."

Amara Cay Resort

10/10 Excellent

"I like Everything!"

Fisher Inn Resort & Marina

10/10 Excellent

"Everything was great!"

Coconut Cove Resort and Marina

10/10 Excellent

"Amazing customer service"

More cheap stays in Windley Key

The Pelican Key Largo Cottages

99340 Overseas Highway Key Largo FL

2.434.504 ₫

2.738.817 ₫ total

15 Sept - 16 Sept

includes taxes & fees

9/10 Wonderful! (1,000 reviews)

Sunset Cove Beach Resort

MM 99.5 Key Largo FL

2.542.752 ₫

2.860.790 ₫ total

17 Sept - 18 Sept

includes taxes & fees

Rock Reef Resort

97850 Overseas Hwy Key Largo FL

2.614.623 ₫

2.941.451 ₫ total

27 Sept - 28 Sept

includes taxes & fees

9.2/10 Wonderful! (1,181 reviews)

Hampton Inn Key Largo Manatee Bay

102400 Overseas Hwy Key Largo FL

3.379.189 ₫

3.801.587 ₫ total

24 Sept - 25 Sept

includes taxes & fees

Creekside Inn

90611 Old Highway Tavernier FL

3.412.105 ₫

3.838.456 ₫ total

20 Sept - 21 Sept

includes taxes & fees

7.8/10 Good! (1,020 reviews)

Marina Del Mar Resort and Marina

527 Caribbean Drive Key Largo FL

3.602.602 ₫

4.782.000 ₫ total

13 Sept - 14 Sept

includes taxes & fees

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Book Hotels in Windley Key on Expedia.com

Find hotels in Windley Key, FL from 2.538.911 ₫

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. Fisher Inn Resort & Marina

2. Drop Anchor

3. Coconut Cove Resort and Marina

4. The Ocean View Inn & Pub

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

6. Chesapeake Beach Resort

7. Cheeca Lodge & Spa

8. Creekside Inn

9. Drift Hotel

10. Ragged Edge Resort & Marina

11. Hadley Resort and Marina

12. Rock Reef Resort

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

14. Sunset Cove Beach Resort

15. Marina Del Mar Resort and Marina

16. Amoray Dive Resort

17. Amara Cay Resort

18. Islander Resort

19. Holiday Inn Key Largo by IHG

20. Lime Tree Bay 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

Rock Reef Resort

Playa Largo Resort & Spa, Autograph Collection

Lime Tree Bay Resort

The Pelican Key Largo Cottages

Islander Resort

Amara Cay Resort

Fisher Inn Resort & Marina

Coconut Cove Resort and Marina

More cheap stays in Windley Key

The Pelican Key Largo Cottages

Sunset Cove Beach Resort

Rock Reef Resort

Hampton Inn Key Largo Manatee Bay

Creekside Inn

Marina Del Mar Resort and Marina

Explore a world of travel with Expedia

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