Top 10 Hotels in Windley Key, FL from ￥13,571 - 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 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.

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.

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

Islamorada

Liosbel

￥37,818

￥54,107 total

includes taxes & fees

Nov 2 - Nov 3

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

2. Drop Anchor

Islamorada

Payman

￥17,614

￥25,350 total

includes taxes & fees

Oct 18 - Oct 19

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

Hailey Ritch and Patrick

￥23,557

￥26,502 total

includes taxes & fees

Oct 26 - Oct 27

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.

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.

4. Fisher Inn Resort & Marina

Islamorada

Siobhan

￥25,138

￥33,440 total

includes taxes & fees

Oct 18 - Oct 19

A bedroom with a large bed, a sliding glass door to a balcony, a wooden cabinet, and a kitchen area with a microwave.

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.

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

Islamorada

Maria

￥29,454

￥33,135 total

includes taxes & fees

Oct 18 - Oct 19

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

A bar area with a thatched roof, wooden chairs, 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 tropical resort with a swimming pool, palm trees, and a waterfall.

6. Cheeca Lodge & Spa

Matecumbe

Kristin

￥29,260

￥44,479 total

includes taxes & fees

Oct 19 - Oct 20

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 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.

7. Islander Resort

Matecumbe

Steven

￥32,885

￥48,555 total

includes taxes & fees

Oct 18 - Oct 19

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

A resort with a thatched-roof structure, palm trees, and lounge chairs on a sandy beach.

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.

8. Hampton Inn Key Largo Manatee Bay

Key Largo

Samantha

￥18,055

￥20,313 total

includes taxes & fees

Oct 26 - Oct 27

A beach with palm trees and lounge chairs.

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

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 balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.

9. Chesapeake Beach Resort

Matecumbe

Phelicia

￥22,175

￥33,840 total

includes taxes & fees

Oct 20 - Oct 21

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

A beach with palm trees, a dock, and lounge chairs.

10. Amara Cay Resort

Matecumbe

Danielle

￥22,973

￥37,407 total

includes taxes & fees

Oct 20 - Oct 21

A dining area with tables set for two, overlooking a beach with palm trees and a sunset view.

A spacious living room with large windows, comfortable seating, and decorative plants.

A poolside area with blue chairs and a thatched-roof structure.

A spacious bar area with high ceilings and large windows, offering views of the ocean.

11. Reefhouse Resort & Marina

Key Largo

Manny

￥31,462

￥41,720 total

includes taxes & fees

Oct 19 - Oct 20

A table with a glass pitcher, a glass with a slice of lime, and a plate with raspberries and a sprig of rosemary.

A beachfront hotel with multiple balconies, a pool, and a beach area with lounge chairs.

A child sitting on a beach with sand toys and a green bucket nearby.

An aerial view of a resort with two large swimming pools surrounded by palm trees and lounge chairs.

12. Baker's Cay Resort Key Largo, Curio Collection by Hilton

Key Largo

Alan

￥42,652

￥56,700 total

includes taxes & fees

Oct 28 - Oct 29

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 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.

13. Sunset Cove Beach Resort

Key Largo

Alexey

￥18,495

￥20,808 total

includes taxes & fees

Oct 20 - Oct 21

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.

An aerial view of a resort with a swimming pool, beach area, and dock.

14. Bayside Inn Key Largo

Key Largo

Lwigy

￥17,216

￥23,321 total

includes taxes & fees

Oct 22 - Oct 23

A balcony with wicker chairs and a small table overlooking a marina with boats and palm trees.

A pool area with lounge chairs, a thatched umbrella, and a marina in the background.

A modern room with a large window, a grey sofa, a lamp, and a view of a pool and palm trees.

A modern kitchen with a curved island, stainless steel appliances, and a menu board.

15. Courtyard by Marriott Key Largo

Key Largo

Anna

￥24,047

￥27,053 total

includes taxes & fees

Oct 27 - Oct 28

An aerial view of a resort with a large pool, palm trees, and a beach.

A beach with clear water, a wooden pier, and lounge chairs under a tree.

A restaurant with wooden tables and chairs, a bar area, and a view of the sea.

A pool area with lounge chairs and umbrellas, a clear sky, and palm trees.

16. Playa Largo Resort & Spa, Autograph Collection

Rock Harbor

Jorge

￥44,110

￥58,340 total

includes taxes & fees

Oct 29 - Oct 30

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

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.

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

17. Holiday Inn Key Largo by IHG

Key Largo

suany

￥25,925

￥29,166 total

includes taxes & fees

Oct 25 - Oct 26

A bathroom with a bathtub, toilet, and sink.

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.

A beach with hammocks under palm trees, a sandy beach, and a clear blue sky.

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

Key Largo

Omar Ahmad

￥16,930

￥24,059 total

includes taxes & fees

Oct 27 - Oct 28

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

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

19. La Jolla Resort

Matecumbe

Brett

￥19,806

￥26,728 total

includes taxes & fees

Oct 18 - Oct 19

A balcony with a view of the sea, a table, and two chairs.

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.

20. Waterside Suites & Marina

Key Largo

Ysabella

￥17,593

￥24,238 total

includes taxes & fees

Nov 1 - Nov 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.

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

Fisher Inn Resort & Marina

10/10 Excellent

"Very nice stay, plenty of room, enjoyed pool & water view. The breakfast was yummy too, loved those special waffles!!!"

Islander Resort

10/10 Excellent

"Very nice experience and cosy hotel in the Keys, super recommended!"

Chesapeake Beach Resort

10/10 Excellent

"Great location"

Rock Reef Resort

10/10 Excellent

"Great place and cheap for what you get. Stayed there twice now"

Lime Tree Bay Resort

10/10 Excellent

"What to say really. We had a n absolute nightmare of a day on our way down to the hotel. We were due to land at Key West at 1200 but that turned into landing in Miami and then an 8 hour delay before finally touching down. The staff at the hotel were great contacting us throughout the day and being so friendly and attentive! We arrived finally at the hotel at 2230 and Robin at the check in was so fantastic staying back for us to be able to be checked in! We even got an upgrade. The only downside was due to the mess caused by flights, we were in the room for just a few hours. The resort was beautiful. The view from The balcony to the sea. The room was just so unbelievable it was like the stuff you get in dreams. Such a beautiful resort, beautiful room and I am certain we will be back! Thank you!"

Reefhouse Resort & Marina

10/10 Excellent

"The room was clean and the property was beautiful."

Waterside Suites & Marina

10/10 Excellent

"Esther was really helpful. Very nice and professional. Room was spotless!! Balcony with a beautiful view."

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."

More cheap stays in Windley Key

Rock Reef Resort

97850 Overseas Hwy Key Largo FL

￥12,063

￥13,571 total

Oct 22 - Oct 23

includes taxes & fees

9.2/10 Wonderful! (1,192 reviews)

The Pelican Key Largo Cottages

99340 Overseas Highway Key Largo FL

￥15,075

￥16,959 total

Nov 2 - Nov 3

includes taxes & fees

Breezy Palms Resort

80015 Overseas Highway Islamorada FL

￥15,510

￥19,972 total

Oct 18 - Oct 19

includes taxes & fees

9/10 Wonderful! (770 reviews)

Hampton Inn Key Largo Manatee Bay

102400 Overseas Hwy Key Largo FL

￥18,055

￥20,313 total

Oct 26 - Oct 27

includes taxes & fees

Sunset Cove Beach Resort

MM 99.5 Key Largo FL

￥18,495

￥20,808 total

Oct 20 - Oct 21

includes taxes & fees

9.2/10 Wonderful! (1,000 reviews)

Creekside Inn

90611 Old Highway Tavernier FL

￥18,552

￥20,871 total

Oct 29 - Oct 30

includes taxes & fees

Hotels in Windley Key with star-rating

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Find hotels in Windley Key, FL from ￥13,571

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

2. Drop Anchor

3. Coconut Cove Resort and Marina

4. Fisher Inn Resort & Marina

5. The Ocean View Inn & Pub

6. Cheeca Lodge & Spa

7. Islander Resort

8. Hampton Inn Key Largo Manatee Bay

9. Chesapeake Beach Resort

10. Amara Cay Resort

11. Reefhouse Resort & Marina

12. Baker's Cay Resort Key Largo, Curio Collection by Hilton

13. Sunset Cove Beach Resort

14. Bayside Inn Key Largo

15. Courtyard by Marriott Key Largo

16. Playa Largo Resort & Spa, Autograph Collection

17. Holiday Inn Key Largo by IHG

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

19. La Jolla Resort

20. Waterside Suites & Marina

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

Fisher Inn Resort & Marina

Islander Resort

Chesapeake Beach Resort

Rock Reef Resort

Lime Tree Bay Resort

Reefhouse Resort & Marina

Waterside Suites & Marina

Sunset Cove Beach Resort

More cheap stays in Windley Key

Rock Reef Resort

The Pelican Key Largo Cottages

Breezy Palms Resort

Hampton Inn Key Largo Manatee Bay

Sunset Cove Beach Resort

Creekside Inn

Hotels in Windley Key with star-rating

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