Top 10 Hotels in Windley Key, FL from ₩141,893 - 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

₩159,793

₩224,677 total

includes taxes & fees

Sep 21 - Sep 22

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

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.

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

2. Drop Anchor

Islamorada

Marianela

₩175,524

₩245,637 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 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 resort with thatched-roof structures, palm trees, and a sandy beach area.

3. Coconut Cove Resort and Marina

Islamorada

Lisa C

₩205,075

₩230,709 total

includes taxes & fees

Sep 1 - Sep 2

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.

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

Islamorada

Dareen

₩241,134

₩371,927 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 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 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.

5. The Ocean View Inn & Pub

Islamorada

Patrice

₩256,412

₩288,453 total

includes taxes & fees

Sep 1 - Sep 2

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

₩207,896

₩311,302 total

includes taxes & fees

Sep 1 - Sep 2

A beach with rows of sun loungers and palm trees.

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

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.

7. Ragged Edge Resort & Marina

Islamorada

Katarzyna

₩126,819

₩142,671 total

includes taxes & fees

Sep 13 - Sep 14

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

8. Cheeca Lodge & Spa

Matecumbe

Mian

₩205,075

₩331,361 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

₩133,161

₩149,807 total

includes taxes & fees

Sep 27 - Sep 28

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

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

Key Largo

WORTHINGTON

₩135,019

₩195,541 total

includes taxes & fees

Sep 7 - Sep 8

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

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

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.

11. Creekside Inn

Tavernier

Cristy

₩170,941

₩192,309 total

includes taxes & fees

Sep 8 - Sep 9

A beach with lounge chairs and a blue umbrella, a pier with boats, and a mural of wings on a wall.

A modern living room with a sofa, a glass coffee table, a TV, and a sliding door leading to a bedroom.

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.

12. Drift Hotel

Key Largo

Sheily

₩164,128

₩200,128 total

includes taxes & fees

Sep 3 - Sep 4

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.

13. Sunset Cove Beach Resort

Key Largo

Melissa

₩161,032

₩181,168 total

includes taxes & fees

Sep 1 - Sep 2

A spacious lobby with a reception desk, seating area, and a large aquarium display.

A swimming pool with lounge chairs and palm trees.

14. Marina Del Mar Resort and Marina

Key Largo

Brenda

₩191,311

₩253,941 total

includes taxes & fees

Sep 1 - Sep 2

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

A pool area with lounge chairs and umbrellas, surrounded by palm trees and buildings.

An aerial view of a marina with docked boats, a building with balconies, and a beach area.

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

15. Hadley Resort and Marina

Matecumbe

RAIBEL

₩159,793

₩224,677 total

includes taxes & fees

Sep 20 - Sep 21

A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.

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

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.

16. La Jolla Resort

Matecumbe

adrian

₩153,049

₩210,897 total

includes taxes & fees

Sep 1 - Sep 2

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 hotel room with a bed, a sofa, a coffee table, a desk with a lamp, and a view of the ocean.

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

17. Amara Cay Resort

Matecumbe

David A

₩203,458

₩329,542 total

includes taxes & fees

Sep 2 - Sep 3

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

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

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

18. Lime Tree Bay Resort

Long Key

Chadwick

₩154,257

₩235,475 total

includes taxes & fees

Sep 2 - Sep 3

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 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.

19. Amoray Dive Resort

Key Largo

Ivette

₩122,230

₩176,224 total

includes taxes & fees

Sep 1 - Sep 2

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

A beachside patio with wooden furniture, a thatched roof, and a view of the ocean.

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.

20. Islander Resort

Matecumbe

Sonia

₩335,827

₩470,709 total

includes taxes & fees

Sep 22 - Sep 23

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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

Cheeca Lodge & Spa

8/10 Good

"I've been visiting Cheeca Lodge for years, and it was always well-maintained and spotless. This time, though, I guess due to the new ownership, there’s been a noticeable decline in cleaning and upkeep."

Amara Cay Resort

10/10 Excellent

"Beautiful!"

Chesapeake Beach Resort

10/10 Excellent

"Lindo y acogedor lugar, cerca del sandbar con marina para poner tu bote. Nuestra eetancia fue excelente. El staff bien amable y atento. Volveremos Gracias"

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."

More cheap stays in Windley Key

The Pelican Key Largo Cottages

99340 Overseas Highway Key Largo FL

₩126,128

₩141,893 total

Sep 1 - Sep 2

includes taxes & fees

9/10 Wonderful! (1,005 reviews)

Creekside Inn

90611 Old Highway Tavernier FL

₩170,941

₩192,309 total

Sep 8 - Sep 9

includes taxes & fees

Drift Hotel

95320 Overseas Hwy Key Largo FL

₩164,128

₩200,128 total

Sep 3 - Sep 4

includes taxes & fees

Hampton Inn Key Largo Manatee Bay

102400 Overseas Hwy Key Largo FL

₩179,447

₩201,878 total

Sep 8 - Sep 9

includes taxes & fees

8.8/10 Excellent! (1,074 reviews)

Breezy Palms Resort

80015 Overseas Highway Islamorada FL

₩127,463

₩214,751 total

Sep 6 - Sep 7

includes taxes & fees

Marina Del Mar Resort and Marina

527 Caribbean Drive Key Largo FL

₩191,311

₩253,941 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 ₩141,893

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

5. The Ocean View Inn & Pub

6. Chesapeake Beach Resort

7. Ragged Edge Resort & Marina

8. Cheeca Lodge & Spa

9. Rock Reef Resort

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

11. Creekside Inn

12. Drift Hotel

13. Sunset Cove Beach Resort

14. Marina Del Mar Resort and Marina

15. Hadley Resort and Marina

16. La Jolla Resort

17. Amara Cay Resort

18. Lime Tree Bay Resort

19. Amoray Dive Resort

20. Islander 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

Cheeca Lodge & Spa

Amara Cay Resort

Chesapeake Beach Resort

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

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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