Best Windley Key Hotels in 2026 from HK$818 - Fully Refundable Options

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Go beyond your typical stay in Windley Key

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

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

Islamorada

Eslita

HK$1,562

HK$2,331 total

includes taxes & fees

29 Sept - 30 Sept

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 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.

2. Drop Anchor

Islamorada

Marianela

HK$939

HK$1,331 total

includes taxes & fees

24 Sept - 25 Sept

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.

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.

3. Fisher Inn Resort & Marina

Islamorada

Alexandra

HK$927

HK$1,299 total

includes taxes & fees

24 Sept - 25 Sept

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 wooden deck with a thatched roof structure, wooden chairs, and a table, overlooking a tropical landscape with palm trees and a clear sky.

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

4. Coconut Cove Resort and Marina

Islamorada

Hailey Ritch and Patrick

HK$1,169

HK$1,315 total

includes taxes & fees

24 Sept - 25 Sept

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 swimming pool with a 5 ft depth marker, surrounded by palm trees and a white picket fence.

5. The Ocean View Inn & Pub

Islamorada

Maria

HK$1,461

HK$1,644 total

includes taxes & fees

27 Sept - 28 Sept

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

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

6. Chesapeake Beach Resort

Matecumbe

Suresh

HK$1,185

HK$1,774 total

includes taxes & fees

24 Sept - 25 Sept

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.

7. Cheeca Lodge & Spa

Matecumbe

RAIBEL

HK$1,169

HK$1,888 total

includes taxes & fees

24 Sept - 25 Sept

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

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

8. Creekside Inn

Tavernier

Terry

HK$1,122

HK$1,263 total

includes taxes & fees

24 Sept - 25 Sept

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 wooden pier leading to a beach with palm trees and a row of beach huts.

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

9. Islander Resort

Matecumbe

John

HK$1,535

HK$2,257 total

includes taxes & fees

29 Sept - 30 Sept

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 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.

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

10. Amara Cay Resort

Matecumbe

MICHAEL

HK$1,212

HK$1,938 total

includes taxes & fees

27 Sept - 28 Sept

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.

A pier with boats docked, a thatched-roof structure, and signs indicating tours and rentals.

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

11. Hadley Resort and Marina

Matecumbe

weder

HK$927

HK$1,299 total

includes taxes & fees

28 Sept - 29 Sept

Two Adirondack chairs on a sandy beach with a wooden pier extending into calm water.

A bedroom with a bed, a television, a dresser, and a door.

A dining area with a wooden table, woven placemats, and chairs.

A bathroom with a white vanity, a mirror, a sink, a cabinet, and a towel rack.

12. Coconut Palm Inn

Tavernier

HK$1,475

HK$1,969 total

includes taxes & fees

24 Sept - 25 Sept

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.

A clear blue swimming pool with a metal railing, surrounded by palm trees and a view of the ocean.

13. Ragged Edge Resort & Marina

Islamorada

Nathalie

HK$1,025

HK$1,153 total

includes taxes & fees

27 Sept - 28 Sept

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

14. La Jolla Resort

Matecumbe

Leslie

HK$759

HK$1,074 total

includes taxes & fees

28 Sept - 29 Sept

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 marina with boats docked along a waterfront, surrounded by buildings and palm trees.

A swimming pool with lounge chairs and umbrellas, a fenced area, and a building with a door.

15. Waterside Suites & Marina

Key Largo

Thuc

HK$961

HK$1,302 total

includes taxes & fees

24 Sept - 25 Sept

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

A beachside seating area with Adirondack chairs and a table, palm trees, and a view of the ocean.

A compact living space with a balcony, a television, and a dining area.

A paved pathway lined with palm trees leading to a beach area with lounge chairs and a view of the ocean.

16. Atlantic Bay Resort

Tavernier

Annie

HK$1,043

HK$1,350 total

includes taxes & fees

28 Sept - 29 Sept

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

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

17. Drift Hotel

Key Largo

kelly

HK$735

HK$916 total

includes taxes & fees

27 Sept - 28 Sept

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

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

Key Largo

Omar Ahmad

HK$770

HK$1,115 total

includes taxes & fees

4 Oct - 5 Oct

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

A marina with multiple boats docked, surrounded by palm trees and buildings.

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.

19. Courtyard by Marriott Key Largo

Key Largo

Jennifer

HK$1,264

HK$1,422 total

includes taxes & fees

27 Sept - 28 Sept

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

A beach with thatched umbrellas, palm trees, and blue lounge chairs.

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

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

20. Reefhouse Resort & Marina

Key Largo

Susan

HK$1,561

HK$2,070 total

includes taxes & fees

28 Sept - 29 Sept

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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

Bayside Inn Key Largo

10/10 Excellent

"Beautiful location, wonderful private beach area with lots of lounge chairs on the two lounge jetties, nice snorkeling area, swimming pool right there, Snook's Restaurant next door with good music. And all of this a short 5 minute drive from a top-notch scuba dive operation (Rainbow Reef Dive Center). What else do you need?! David Crymes Junction City, OR ;"

Rock Reef Resort

8/10 Good

"I enjoyed my stay and plan to go back"

Fisher Inn Resort & Marina

10/10 Excellent

"This place was the best place to stay I've ever been ever it is wonderful there's nothing not to like about this place the ocean the pool the people the place everybody's so nice and accommodating they will do anything they can to make sure you're happy it's paradise in paradise I would suggest to stay at this place anytime it would be a mistake not to"

Chesapeake Beach Resort

10/10 Excellent

"We had a wonderful stay at this hotel. I stayed with my mom, sister, and niece, and we truly loved the property. The location is great, the hotel is beautiful, and we really enjoyed the amenities and our time together. Overall, it was a very nice experience. The only area I feel could use some improvement is the late checkout process. I requested a late checkout until 2:00 PM because we wanted to enjoy the amenities a little longer before leaving. The property did not appear to be fully booked, so I was hoping there might be some flexibility, but unfortunately my request was not accommodated. By the time I returned to the room, packed everything, and was getting ready to leave, it was close to 1:00 PM. A member of the housekeeping staff knocked on the door and spoke to us in a way that felt rushed and unnecessarily rude, saying, “Don’t you know you were supposed to leave by 11:00 AM?” That interaction made us feel very uncomfortable and was disappointing, especially after such an enjoyable stay. I completely understand that hotels have checkout policies and that late checkout cannot always be guaranteed. However, I believe a little more flexibility when occupancy allows, along with a more courteous approach from housekeeping, would make the guest experience even better. Aside from that situation, we really loved the hotel, the location, and our stay. With a little improvement in communication and hospitality around checkout, it would be an even better experience."

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

10/10 Excellent

"This place feels like paradise! It is so calm and relaxing yet vibrant and fun. We had amazing weather all weekend. The ocean was so nice. The poolside trivia, scavenger hunt, smores and silent disco were so fun. The live music was a hit! We cannot WAIT to come back soon!"

Islander Resort

10/10 Excellent

"Loved the property!!! So quiet and relaxing! Great bar, pools, beaches!!!! Would absolutely stay again!"

Hampton Inn Key Largo Manatee Bay

10/10 Excellent

"Nice hotel, continuing to update. Enjoyed the outdoor bar and sunset view. Beautiful location for sunset"

Sunset Cove Beach Resort

8/10 Good

"Takes pets for reasonable rate; but no pool"

Amara Cay Resort

8/10 Good

"We had a great stay and overall I would definitely return as it’s a wonderful property. The hotel rooms are spacious and clean. I appreciated the responsiveness of staff and communication via text and ability to make requests via QR code. I would say breakfast was lackluster and the service was extremely slow. Furthermore, I ordered two scrambled eggs and was served powdered eggs which tasted absolutely disgusting. I send that back, and was asked if I would like “hard shell” eggs instead. I thought this was very odd! You wouldn’t expect this at a resort of this level!"