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

Find Cheap Hotels in Windley Key, FL

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Windley Key Cheap Hotels

Tonight
Sep 30 - Oct 1
Tomorrow
Oct 1 - Oct 2
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Windley Key cheap hotels

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

1. Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
Islamorada
United States
Alexandra
NT$4,295
NT$5,869 total
includes taxes & fees
Oct 13 - Oct 14
Fisher Inn Resort & Marina
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 beach with palm trees, a thatched umbrella, and lounge chairs.
A pool area with lounge chairs and a sign indicating a drop-off zone.

2. Drop Anchor

Drop Anchor
Islamorada
United States
Payman
NT$4,179
NT$5,814 total
includes taxes & fees
Oct 6 - Oct 7
Drop Anchor
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 beachside resort with thatched-roof huts, palm trees, and a sandy area with rocks and wooden 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.

3. Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
Islamorada
United States
Hailey Ritch and Patrick
NT$4,735
NT$5,327 total
includes taxes & fees
Oct 1 - Oct 2
Coconut Cove Resort and Marina
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.
An outdoor dining area with round tables and chairs, a thatched roof, and a view of the sea.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
Canada
Eslita
NT$6,866
NT$10,057 total
includes taxes & fees
Oct 18 - Oct 19
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 bathroom with a sink, toilet, and shower. There is a mirror above the sink and a shelf with towels.
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 swimming pool with a 5 ft depth marker, surrounded by palm trees and a white picket fence.

5. The Ocean View Inn & Pub

The Ocean View Inn & Pub
Islamorada
United States
Maria
NT$5,921
NT$6,660 total
includes taxes & fees
Oct 1 - Oct 2
The Ocean View Inn & Pub
A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.
A bedroom with a bed, two chairs, a sofa, a TV, and a large window with a 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.

6. La Jolla Resort

La Jolla Resort
Matecumbe
United States
Kayla
NT$3,075
NT$4,353 total
includes taxes & fees
Oct 6 - Oct 7
La Jolla Resort
A beach with hammocks under palm trees, a sandy beach, and a clear blue sky.
A resort with a pool, multiple buildings, and a waterfront view.
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.

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

Dove Creek Resort & Marina, Trademark Collection by Wyndham
Key Largo
United States
Omar Ahmad
NT$3,261
NT$4,676 total
includes taxes & fees
Oct 6 - Oct 7
Dove Creek Resort & Marina, Trademark Collection by Wyndham
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.

8. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
United States
Suresh
NT$4,800
NT$7,188 total
includes taxes & fees
Oct 6 - Oct 7
Chesapeake Beach Resort
A beach with palm trees, thatched-roof huts, and lounge chairs.
A modern kitchen with a microwave, stove, and refrigerator. There is a dining area with a table and chairs.
A building facade with the text "Buzzy Plims" and a website address. There are two potted plants and a staircase leading up to the entrance.
A beach with thatched umbrellas, palm trees, and lounge chairs.

9. Breezy Palms Resort

Breezy Palms Resort
Matecumbe
United States
Zack
NT$2,608
NT$3,444 total
includes taxes & fees
Oct 4 - Oct 5
Breezy Palms 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 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.

10. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
United States
RAIBEL
NT$4,754
NT$7,681 total
includes taxes & fees
Oct 1 - Oct 2
Cheeca Lodge & Spa
View all properties

Top Windley Key Hotel Reviews

Lime Tree Bay Resort

Lime Tree Bay Resort

10/10 Excellent
"Beautiful location, great amenities, and comfortable rooms"
Michael 7-night trip
Posted 17 hours ago
Lime Tree Bay Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"All the place is amazing but the rooms needs a little be of work to upgrade, and the beach was not as we imagined"
Daniel 3-night trip
Posted 17 hours ago
Cheeca Lodge & Spa
Islander Resort

Islander Resort

10/10 Excellent
"Amazing place would definitely recommend"
Steven 2-night trip
Posted 2 days ago
Islander Resort
Amara Cay Resort

Amara Cay Resort

8/10 Good
"This resort was absolutely beautiful!! The pool was amazing, a resort style pool. The resort had its own private beach area and a dock. Had plenty of seating everywhere, many cool sitting areas around the property. The only negative thing I could say is that the staff didn’t pick up trash and towels around the pool which seemed odd and it was off season so it wasn’t busy. It’s such a beautiful resort that I would think that would be a priority to keep it clean. Another cool thing is that they have a water taxi and shuttle to their 2 sister resorts which you can utilize all of those amenities as well. They also included bike rentals, paddle boards and kayaking on site which is convenient. You can also bring your private boat there and leave it at the dock for a fee. I would absolutely stay there again!"
Melissa 1-night trip
Posted 2 days ago
Amara Cay Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

10/10 Excellent
"Ya’ll just need a microwave."
Nathalee 3-night trip
Posted 2 days ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Waterside Suites & Marina

Waterside Suites & Marina

10/10 Excellent
"i loved this place beautiful hotel full kitchen perfect for a little trip 100% recommend"
Ysabella 2-night trip
Posted 2 days ago
Waterside Suites & Marina
Sunset Cove Beach Resort

Sunset Cove Beach Resort

10/10 Excellent
"Great getaway for weekend and bring the dog"
Brian 4-night trip
Posted 4 days ago
Sunset Cove Beach Resort

Explore a world of travel with Expedia