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.

Two people relaxing on sun loungers by a poolside with a view of the ocean and palm trees in the background.

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

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

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

A wooden boardwalk leading to a building with a brick wall and a white roof.

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

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 beach with palm trees, a thatched-roof hut, and lounge 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.

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

3. Coconut Cove Resort and Marina

Islamorada

Lisa C

₩205,075

₩230,709 total

includes taxes & fees

Aug 31 - Sep 1

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

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

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

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

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

Islamorada

Ana

₩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 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

Patrice

₩256,412

₩288,453 total

includes taxes & fees

Aug 31 - Sep 1

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 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

Yeniaris

₩207,896

₩311,302 total

includes taxes & fees

Aug 31 - Sep 1

A beach with rows of sun loungers and palm trees.

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.

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

7. Ragged Edge Resort & Marina

Islamorada

Katarzyna

₩132,393

₩148,942 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 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.

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

8. Cheeca Lodge & Spa

Matecumbe

Jessica

₩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 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.

9. Rock Reef Resort

Rock Harbor

manuel

₩133,161

₩149,807 total

includes taxes & fees

Aug 31 - Sep 1

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

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

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

Key Largo

Mae L

₩135,019

₩195,540 total

includes taxes & fees

Aug 31 - Sep 1

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 beach with lounge chairs, kayaks, and a wooden pier.

A tree with string lights, a wooden bench, and a building in the background.

12. Drift Hotel

Key Largo

Sheily

₩160,115

₩195,614 total

includes taxes & fees

Sep 14 - Sep 15

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

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

13. Sunset Cove Beach Resort

Key Largo

Melissa

₩161,032

₩181,168 total

includes taxes & fees

Sep 1 - Sep 2

A swimming pool with lounge chairs and palm trees.

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

14. Marina Del Mar Resort and Marina

Key Largo

Brenda

₩191,311

₩253,941 total

includes taxes & fees

Aug 31 - Sep 1

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 beachfront property with a white building, a balcony with a white railing, and palm trees.

A beachfront property with a staircase leading to a light blue building, palm trees, and a clear view of the ocean.

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

16. La Jolla Resort

Matecumbe

adrian

₩142,038

₩198,509 total

includes taxes & fees

Aug 31 - Sep 1

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.

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

17. Amara Cay Resort

Matecumbe

David A

₩203,458

₩329,542 total

includes taxes & fees

Sep 1 - Sep 2

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

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

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

18. Lime Tree Bay Resort

Long Key

Chadwick

₩154,257

₩235,475 total

includes taxes & fees

Sep 1 - Sep 2

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 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.

19. Amoray Dive Resort

Key Largo

Ivette

₩122,230

₩176,224 total

includes taxes & fees

Aug 31 - Sep 1

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

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.

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

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

Playa Largo Resort & Spa, Autograph Collection

8/10 Good

"Great place just be prepared for many hidden fees that are like 50% more than what you pay for the actual stay. Resort fees, parking fees, etc. very nice staff. Rooms are nice, bathrooms outdated."

Bayside Inn Key Largo

10/10 Excellent

"Great place! Close to everything in Key Largo. Staff was great. We will need to get a bigger room next time we visit. We will be back."

Hampton Inn Key Largo Manatee Bay

10/10 Excellent

"All was great"

The Pelican Key Largo Cottages

8/10 Good

"Nice stay, good dock and beach area"

Islander Resort

10/10 Excellent

"It’s a beautiful property right on the water with very nice pool area and right near everything in Islamorada"

Waterside Suites & Marina

10/10 Excellent

"Me encantó la verdad. Fuimos un grupo familiar todos. Pero el echo de la cocina. El barbecue abajo. La piscina calentica. La verdad a nosotros nos encantó."

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

10/10 Excellent

"I’d recommend getting breakfast locally instead of the resort’s breakfast. Very friendly and helpful staff."

Drop Anchor

8/10 Good

"Shower didn’t get super hot & not the best water pressure. Keep blinds closed in summer as the room got very hot and the a/c unit struggled to keep the room cool even at night. Could use a shade for the kitten window to help with this. Full length mirror in the room would’ve been nice as well. Overall nice property but a little older & can use some revamping"

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! (1,002 reviews)

Breezy Palms Resort

80015 Overseas Highway Islamorada FL

₩137,455

₩176,585 total

Sep 1 - Sep 2

includes taxes & fees

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

₩160,115

₩195,614 total

Sep 14 - Sep 15

includes taxes & fees

Hampton Inn Key Largo Manatee Bay

102400 Overseas Hwy Key Largo FL

₩179,447

₩201,878 total

Sep 7 - Sep 8

includes taxes & fees

8.8/10 Excellent! (1,071 reviews)

Marina Del Mar Resort and Marina

527 Caribbean Drive Key Largo FL

₩191,311

₩253,941 total

Aug 31 - Sep 1

includes taxes & fees

8.6/10 Excellent! (1,873 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

Playa Largo Resort & Spa, Autograph Collection

Bayside Inn Key Largo

Hampton Inn Key Largo Manatee Bay

The Pelican Key Largo Cottages

Islander Resort

Waterside Suites & Marina

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

Drop Anchor

More cheap stays in Windley Key

The Pelican Key Largo Cottages

Breezy Palms Resort

Creekside Inn

Drift Hotel

Hampton Inn Key Largo Manatee Bay

Marina Del Mar Resort and Marina

Hotels in Windley Key with star-rating

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