A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.

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Check prices for these dates

Tonight
18 Oct - 19 Oct
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19 Oct - 20 Oct
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23 Oct - 25 Oct
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30 Oct - 1 Nov

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Our top choices for Windley Key hotels

A clear blue pool surrounded by palm trees and a thatched-roof structure, with a view of the ocean in the background.
A resort with thatched-roof structures, palm trees, and a sandy beach area.
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.

1. Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
Islamorada
United States
Hailey Ritch and Patrick
NZ$297
includes taxes & fees
26 Oct - 27 Oct
Coconut Cove Resort and Marina
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 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.

2. Drop Anchor

Drop Anchor
Islamorada
United States
Payman
NZ$284
includes taxes & fees
19 Oct - 20 Oct
Drop Anchor
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 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.

3. Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
Islamorada
United States
Robyn
NZ$374
includes taxes & fees
19 Oct - 20 Oct
Fisher Inn Resort & Marina
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.
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.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
United States
Liosbel
NZ$605
includes taxes & fees
2 Nov - 3 Nov
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A bedroom with a large bed, a sliding glass door to a balcony, a wooden cabinet, and a kitchen area with a microwave.
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.
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.

5. The Ocean View Inn & Pub

The Ocean View Inn & Pub
Islamorada
United States
Maria
NZ$371
includes taxes & fees
19 Oct - 20 Oct
The Ocean View Inn & Pub
A beach with palm trees and lounge chairs.
A swimming pool with clear blue water, surrounded by a white deck and a black metal fence.
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 waterfront hotel with multiple floors, palm trees, and a calm reflective pool.

6. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
United States
Phelicia
NZ$376
includes taxes & fees
20 Oct - 21 Oct
Chesapeake Beach Resort
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 bar area with a wooden counter, bar stools, and potted plants.
A paved pathway leading to a beach with palm trees and a view of the ocean.

7. Islander Resort

Islander Resort
Matecumbe
United States
Clara
NZ$518
includes taxes & fees
15 Nov - 16 Nov
Islander Resort
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.
A hand holding a card with the Bayside Inn logo, palm trees, and a beach setting in the background.
A beach with palm trees, a sandy path, and a building with a balcony.

8. Bayside Inn Key Largo

Bayside Inn Key Largo
Key Largo
United States
Rosa
NZ$267
includes taxes & fees
19 Oct - 20 Oct
Bayside Inn Key Largo
A beach with thatched umbrellas, wooden chairs, and a wooden pier 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.
A balcony with a view of the sea, a beach, and a thatched hut.

9. Sunset Cove Beach Resort

Sunset Cove Beach Resort
Key Largo
Canada
Alexey
NZ$208
includes taxes & fees
4 Nov - 5 Nov
Sunset Cove Beach Resort
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.

10. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
United States
James
NZ$478
includes taxes & fees
20 Oct - 21 Oct
Cheeca Lodge & Spa
A wooden deck with rustic furniture, a grill, and a view of the beach 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.
A beachfront property with a white building, a balcony with a white railing, and palm trees.

11. La Jolla Resort

La Jolla Resort
Matecumbe
United States
Brett
NZ$335
includes taxes & fees
22 Oct - 23 Oct
La Jolla Resort
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.
An aerial view of a resort with a swimming pool, palm trees, and a dock.
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

Amara Cay Resort
Matecumbe
United States
Danielle
NZ$412
includes taxes & fees
20 Oct - 21 Oct
Amara Cay Resort
A balcony with a view of the sea, a table, and two chairs.
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.
A bedroom with a bed, a TV mounted on the wall, a window with blinds, and a chandelier.

13. Waterside Suites & Marina

Waterside Suites & Marina
Key Largo
United States
Ysabella
NZ$269
includes taxes & fees
29 Oct - 30 Oct
Waterside Suites & Marina
A beach with a wooden pier, palm trees, and a clear blue sky.
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.
A beach with palm trees, lounge chairs, and a view of the ocean.

14. Rock Reef Resort

Rock Reef Resort
Rock Harbor
United States
Jared
NZ$152
includes taxes & fees
27 Oct - 28 Oct
Rock Reef Resort
A beach with two thatched umbrellas, three sun loungers, and a view of the sea with boats.
A waterfront property with a large building, a dock, lounge chairs, and a thatched-roof area.
A marina with docks, lounge chairs, and a clear view of the water.
A modern kitchen with wooden cabinets, a central island with stools, and a ceiling fan.

15. Dolphin Point Villas

Dolphin Point Villas
Key Largo
United States
Ernest
NZ$269
includes taxes & fees
25 Oct - 26 Oct
Dolphin Point Villas
Terrace/patio
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 beach with palm trees and a clear view of the ocean.

16. Lime Tree Bay Resort

Lime Tree Bay Resort
Long Key
United States
Christopher Michael
NZ$326
includes taxes & fees
19 Oct - 20 Oct
Lime Tree Bay Resort
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 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.
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.

17. Drift Hotel

Drift Hotel
Key Largo
United States
kelly
NZ$240
includes taxes & fees
21 Oct - 22 Oct
Drift Hotel
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 modern kitchen with a built-in stove, a large island, and a view to a balcony with outdoor seating.
A resort with a pool, multiple buildings, and a waterfront view.

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

Dove Creek Resort & Marina, Trademark Collection by Wyndham
Key Largo
United States
Omar Ahmad
NZ$269
includes taxes & fees
26 Oct - 27 Oct
Dove Creek Resort & Marina, Trademark Collection by Wyndham
A beach with lounge chairs, palm trees, and a view of the water.
A spacious bedroom with a bed, a dresser, a television, and a view of the sea through the window.
A paved pathway lined with palm trees leading to a beach area with lounge chairs and a view of the ocean.
A compact living space with a balcony, a television, and a dining area.

19. Atlantic Bay Resort

Atlantic Bay Resort
Tavernier
United States
Annette
NZ$311
includes taxes & fees
19 Oct - 20 Oct
Atlantic Bay Resort
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 sunset over a calm body of water with a dock and lounge chairs.
A beach scene with colorful Adirondack chairs, a blue umbrella, and a view of the ocean.

20. Seafarer Key Largo

Seafarer Key Largo
Rock Harbor
United States
Soraya
NZ$252
includes taxes & fees
20 Oct - 21 Oct
Seafarer Key Largo
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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
A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.

Top Windley Key Hotel Reviews

Recent Reviews in Windley Key

Rock Reef Resort

Rock Reef Resort

8/10 Good
"Property was nice, room was cute, but sad the pool was closed."
Shayne 1-night trip
Posted 1 hour ago
Rock Reef Resort
Bayside Inn Key Largo

Bayside Inn Key Largo

10/10 Excellent
"The room was very clean and comfortable. Best shower ever! Nice shampoo, conditioner, and body lotion. Great fluffy towels, and ice cold air conditioning… What more could you want? Great location next to snooks restaurant/bar. Refreshing little pool next to a beach if you wanna sit in the sand. Cute chickens, roosters, and iguanas roaming around. Walking distance to Burger King, Starbucks, sandal, factory, Walgreens… Just a great hotel and a great location!"
Susan 7-night trip
Posted 12 hours ago
Bayside Inn Key Largo
Islander Resort

Islander Resort

10/10 Excellent
"Great resort for families with children"
Bryan 4-night trip
Posted 13 hours ago
Islander Resort
Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Super el hotel"
Liset 1-night trip
Posted 19 hours ago
Chesapeake Beach Resort
Reefhouse Resort & Marina

Reefhouse Resort & Marina

8/10 Good
"Room are a little dated but overall nice. Pool and beach area were well maintained. We got couples massages and those were great. Pricing for them was reasonable. We would come back again!"
Austin 3-night trip
Posted 20 hours ago
Reefhouse Resort & Marina
Waterside Suites & Marina

Waterside Suites & Marina

10/10 Excellent
"Esther was really helpful. Very nice and professional. Room was spotless!! Balcony with a beautiful view."
Manuel 1-night trip
Posted 4 days ago
Waterside Suites & Marina
Sunset Cove Beach Resort

Sunset Cove Beach Resort

10/10 Excellent
"Everything was wonderful, clean room, nice and cool. Beach area had floats and paddle boards for guest use. Enjoyed a short walk to a great restaurant."
Tracy 1-night trip
Posted 6 days ago
Sunset Cove Beach Resort

More cheap accommodation in Windley Key

Rock Reef Resort

Rock Reef Resort

97850 Overseas Hwy Key Largo FL
NZ$152
27 Oct - 28 Oct
includes taxes & fees
9.2/10 Wonderful! (1,194 reviews)
Rock Reef Resort
The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

99340 Overseas Highway Key Largo FL
NZ$185
26 Oct - 27 Oct
includes taxes & fees
The Pelican Key Largo Cottages
Sunset Cove Beach Resort

Sunset Cove Beach Resort

MM 99.5 Key Largo FL
NZ$208
4 Nov - 5 Nov
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
Sunset Cove Beach Resort
Breezy Palms Resort

Breezy Palms Resort

80015 Overseas Highway Islamorada FL
NZ$223
19 Oct - 20 Oct
includes taxes & fees
Breezy Palms Resort
Hampton Inn Key Largo Manatee Bay

Hampton Inn Key Largo Manatee Bay

102400 Overseas Hwy Key Largo FL
NZ$233
25 Oct - 26 Oct
includes taxes & fees
8.8/10 Excellent! (1,111 reviews)
Hampton Inn Key Largo Manatee Bay
Creekside Inn

Creekside Inn

90611 Old Highway Tavernier FL
NZ$268
18 Nov - 19 Nov
includes taxes & fees
Creekside Inn

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