Top 10 Hotels in Windley Key, FL from ￥12,584 - Competitive Prices

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 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.

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

￥18,587

￥26,134 total

includes taxes & fees

Sep 21 - Sep 22

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

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.

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

2. Drop Anchor

Islamorada

Marianela

￥20,417

￥28,571 total

includes taxes & fees

Sep 1 - Sep 2

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

Lisa C

￥22,899

￥25,761 total

includes taxes & fees

Sep 2 - Sep 3

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.

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

Islamorada

Dareen

￥28,048

￥43,261 total

includes taxes & fees

Sep 7 - Sep 8

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 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.

5. The Ocean View Inn & Pub

Islamorada

Patrice

￥29,825

￥33,552 total

includes taxes & fees

Sep 1 - Sep 2

A beach with palm trees and lounge chairs.

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.

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

6. Chesapeake Beach Resort

Matecumbe

Suresh

￥23,456

￥35,393 total

includes taxes & fees

Sep 1 - Sep 2

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 sofa, a glass coffee table, a TV, and a sliding door leading to a bedroom.

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.

7. Drift Hotel

Key Largo

Sheily

￥19,090

￥23,278 total

includes taxes & fees

Sep 2 - Sep 3

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

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.

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

8. Cheeca Lodge & Spa

Matecumbe

Mian

￥23,853

￥38,542 total

includes taxes & fees

Sep 7 - Sep 8

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

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

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

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

9. Rock Reef Resort

Rock Harbor

manuel

￥15,018

￥16,896 total

includes taxes & fees

Sep 10 - Sep 11

A beach with rows of sun loungers and palm trees.

A spacious room with a high ceiling, a ceiling fan, a dining table with chairs, a sofa, and a television mounted on the wall.

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

Katarzyna

￥11,185

￥12,584 total

includes taxes & fees

Sep 1 - Sep 2

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

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

11. Creekside Inn

Tavernier

Cristy

￥19,883

￥22,368 total

includes taxes & fees

Sep 8 - Sep 9

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.

12. Amara Cay Resort

Matecumbe

David A

￥21,773

￥36,202 total

includes taxes & fees

Sep 2 - Sep 3

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

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

13. Hampton Inn Key Largo Manatee Bay

Key Largo

Susanna

￥20,873

￥23,482 total

includes taxes & fees

Sep 7 - Sep 8

A white building with a purple door, surrounded by palm trees.

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

A bedroom with a bed, nightstands, a bench, a TV, a painting, and a view through a glass door.

A beach with a boat docked near the shore, a thatched-roof structure, and palm trees.

14. Amoray Dive Resort

Key Largo

Ivette

￥14,218

￥20,498 total

includes taxes & fees

Sep 1 - Sep 2

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

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

A clear blue pool surrounded by palm trees and a thatched-roof structure, with a sign indicating no diving.

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

15. Kona Kai Resort and Gallery - Adults Only

Rock Harbor

Michelle

￥19,082

￥25,970 total

includes taxes & fees

Sep 1 - Sep 2

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.

16. Waterside Suites & Marina

Key Largo

Harry

￥17,461

￥24,146 total

includes taxes & fees

Sep 1 - Sep 2

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.

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.

17. Hadley Resort and Marina

Matecumbe

RAIBEL

￥18,586

￥26,135 total

includes taxes & fees

Sep 20 - Sep 21

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 bakery display case with various muffins and frittatas labeled with flavors like blueberry, cranberry orange, banana walnut, chocolate, egg cheese vegetable fritta, egg sausage fritta, and egg cheese fritta.

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

18. Seafarer Key Largo

Rock Harbor

Susan

￥15,373

￥19,545 total

includes taxes & fees

Sep 7 - Sep 8

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 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.

19. Coconut Palm Inn

Tavernier

judith

￥30,113

￥40,182 total

includes taxes & fees

Sep 3 - Sep 4

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.

20. Sunset Cove Beach Resort

Key Largo

Melissa

￥18,356

￥20,651 total

includes taxes & fees

Sep 1 - Sep 2

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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.

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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

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

10/10 Excellent

"we loved it !!!"

Bayside Inn Key Largo

10/10 Excellent

"Excellent"

Holiday Inn Key Largo by IHG

10/10 Excellent

"This was a perfect spot to stay, very convenient. Within walking distance to the dive shop we used."

Drop Anchor

10/10 Excellent

"It was quite and clean. Feels like home"

The Pelican Key Largo Cottages

10/10 Excellent

"Room was old"

Hampton Inn Key Largo Manatee Bay

8/10 Good

"I believe if they weren't in the midst of redecorating the rooms the scores would have been higher. They did a very good job of keeping the disruption to a minimum as well as keeping the grounds and parking as maintained as possible considering they had a lot of building supplies all around the property to accomplish the renovations. All-in all it was very good stay."

Cheeca Lodge & Spa

10/10 Excellent

"Excellent stay."

Amara Cay Resort

10/10 Excellent

"Muy buena atención desde Que llegamos ala recepción todo ordenado y limpio"

Islander Resort

10/10 Excellent

"Super quit and nice hotel, staff 5 stars but you can’t fish is just for fun and catch and relief"

More cheap stays in Windley Key

The Pelican Key Largo Cottages

99340 Overseas Highway Key Largo FL

￥14,377

￥16,173 total

Sep 1 - Sep 2

includes taxes & fees

9/10 Wonderful! (1,005 reviews)

Creekside Inn

90611 Old Highway Tavernier FL

￥19,883

￥22,368 total

Sep 8 - Sep 9

includes taxes & fees

Drift Hotel

95320 Overseas Hwy Key Largo FL

￥19,090

￥23,278 total

Sep 2 - Sep 3

includes taxes & fees

Hampton Inn Key Largo Manatee Bay

102400 Overseas Hwy Key Largo FL

￥20,873

￥23,482 total

Sep 7 - Sep 8

includes taxes & fees

8.8/10 Excellent! (1,074 reviews)

Breezy Palms Resort

80015 Overseas Highway Islamorada FL

￥14,826

￥24,978 total

Sep 6 - Sep 7

includes taxes & fees

Marina Del Mar Resort and Marina

527 Caribbean Drive Key Largo FL

￥22,253

￥29,537 total

Sep 1 - Sep 2

includes taxes & fees

8.6/10 Excellent! (1,876 reviews)

Hotels in Windley Key with star-rating

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Find hotels in Windley Key, FL from ￥12,584

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. Drop Anchor

3. Coconut Cove Resort and Marina

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

5. The Ocean View Inn & Pub

6. Chesapeake Beach Resort

7. Drift Hotel

8. Cheeca Lodge & Spa

9. Rock Reef Resort

10. Ragged Edge Resort & Marina

11. Creekside Inn

12. Amara Cay Resort

13. Hampton Inn Key Largo Manatee Bay

14. Amoray Dive Resort

15. Kona Kai Resort and Gallery - Adults Only

16. Waterside Suites & Marina

17. Hadley Resort and Marina

18. Seafarer Key Largo

19. Coconut Palm Inn

20. Sunset Cove Beach 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

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

Bayside Inn Key Largo

Holiday Inn Key Largo by IHG

Drop Anchor

The Pelican Key Largo Cottages

Hampton Inn Key Largo Manatee Bay

Cheeca Lodge & Spa

Amara Cay Resort

Islander Resort

More cheap stays in Windley Key

The Pelican Key Largo Cottages

Creekside Inn

Drift Hotel

Hampton Inn Key Largo Manatee Bay

Breezy Palms Resort

Marina Del Mar Resort and Marina

Hotels in Windley Key with star-rating

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