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

Windley Key Budget Hotels from RM441

  • 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 Budget Hotels

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

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 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.
A man standing next to a boat on a wooden dock with a chain barrier, palm trees, and a building in the background.

1. Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
Islamorada
United States
Alexandra
RM552
RM754 total
includes taxes & fees
26 Oct - 27 Oct
Fisher Inn Resort & 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 wooden boardwalk leading to a building with a brick wall and a white roof.
A pool area with lounge chairs and a sign indicating a drop-off zone.

2. Drop Anchor

Drop Anchor
Islamorada
United States
Payman
RM537
RM747 total
includes taxes & fees
5 Oct - 6 Oct
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 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

Coconut Cove Resort and Marina
Islamorada
United States
Hailey Ritch and Patrick
RM608
RM684 total
includes taxes & fees
4 Oct - 5 Oct
Coconut Cove Resort and 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.
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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
Canada
Eslita
RM879
RM1,287 total
includes taxes & fees
18 Oct - 19 Oct
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 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.
A bedroom with a bed, a nightstand, a chair, and a door.

5. The Ocean View Inn & Pub

The Ocean View Inn & Pub
Islamorada
United States
Maria
RM761
RM856 total
includes taxes & fees
1 Oct - 2 Oct
The Ocean View Inn & Pub
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.

6. La Jolla Resort

La Jolla Resort
Matecumbe
United States
Kayla
RM395
RM559 total
includes taxes & fees
6 Oct - 7 Oct
La Jolla Resort
A beach with hammocks under palm trees, a sandy beach, and a clear blue sky.
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 hotel room with a bed, a TV, a sofa, and a balcony with a view.

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

Dove Creek Resort & Marina, Trademark Collection by Wyndham
Key Largo
United States
Omar Ahmad
RM419
RM601 total
includes taxes & fees
6 Oct - 7 Oct
Dove Creek Resort & Marina, Trademark Collection by Wyndham
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 waterfront hotel with multiple floors, palm trees, and a calm reflective pool.
A swimming pool with clear blue water, surrounded by a white deck and a black metal fence.

8. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
United States
Suresh
RM617
RM923 total
includes taxes & fees
7 Oct - 8 Oct
Chesapeake Beach Resort
A beach with palm trees, thatched-roof huts, and lounge 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.
A living room with a sofa, armchair, coffee table, and lamp. There is a dining area with a table and chairs. The room has a kitchen area with a stove and cabinets.

9. Breezy Palms Resort

Breezy Palms Resort
Matecumbe
United States
Zack
RM334
RM441 total
includes taxes & fees
1 Oct - 2 Oct
Breezy Palms Resort
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 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.

10. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
United States
RAIBEL
RM608
RM983 total
includes taxes & fees
1 Oct - 2 Oct
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 6 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 6 hours ago
Cheeca Lodge & Spa
Islander Resort

Islander Resort

10/10 Excellent
"Amazing place would definitely recommend"
Steven 2-night trip
Posted 1 day 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 1 day 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 3 days ago
Sunset Cove Beach Resort

Explore a world of travel with Expedia