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

Next weekend
25 Sept - 27 Sept
In two weeks
2 Oct - 4 Oct
In one month
16 Oct - 18 Oct
In two months
13 Nov - 15 Nov
No exact matches found, but these alternatives could be just right

Recommended hotels in Windley Key

A beachside patio with white furniture, palm trees, and a thatched umbrella.

1. Drop Anchor

Drop Anchor
3.0 star property
Islamorada
8.6 out of 10, Excellent, (1,004 reviews)
"Great location,"
United States
Marianela
The price is AU$216
includes taxes & fees
17 Sept - 18 Sept
Drop Anchor
A beachfront hotel with a pool, beach chairs, and a view of the ocean at sunset.

2. Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.2 out of 10, Very good, (1,004 reviews)
"Love that they have a food truck on the property!"
United States
Alexandra
The price is AU$218
includes taxes & fees
22 Sept - 23 Sept
Fisher Inn Resort & Marina
A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
4.0 star property
Islamorada
9.0 out of 10, Wonderful, (272 reviews)
"Beautiful place Great beds Lots of dining options"
Canada
Eslita
The price is AU$391
includes taxes & fees
28 Sept - 29 Sept
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A clear blue pool surrounded by palm trees and a thatched-roof structure, with a view of the ocean in the background.

4. Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (290 reviews)
"Clean room, helpful staff, very friendly and welcoming"
United States
Jasmine
The price is AU$235
includes taxes & fees
17 Sept - 18 Sept
Coconut Cove Resort and Marina
A bedroom with a large bed, a sliding glass door to a balcony, a wooden cabinet, and a kitchen area with a microwave.

5. The Ocean View Inn & Pub

The Ocean View Inn & Pub
2.0 star property
Islamorada
9.2 out of 10, Wonderful, (31 reviews)
"Very friendly staff"
United States
Maria
The price is AU$294
includes taxes & fees
22 Sept - 23 Sept
The Ocean View Inn & Pub
A beach with palm trees and lounge chairs.

6. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,780 reviews)
"Excellent location, nice breakfast."
United States
Suresh
The price is AU$310
includes taxes & fees
24 Sept - 25 Sept
Chesapeake Beach Resort
A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.

7. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,000 reviews)
"Loved this place! driving in I wasn’t too sure but when we open the door to our King suite absolutely stunning clean smelled amazing and walk right up to the water. You can paddleboard kayak. We loved our stay."
United States
Tamara
The price is AU$212
includes taxes & fees
22 Sept - 23 Sept
La Jolla Resort
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

8. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,121 reviews)
"Property is beautiful, staff is great and overall an amazing place to stay."
United States
Sonia
The price is AU$427
includes taxes & fees
30 Sept - 1 Oct
Islander Resort
A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.

9. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,440 reviews)
"Excellent hotel to spend good time with friends and family, just amazing."
United States
RAIBEL
The price is AU$321
includes taxes & fees
29 Sept - 30 Sept
Cheeca Lodge & Spa
A beach with rows of sun loungers and palm trees.

10. Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
2.5 star property
Islamorada
9.6 out of 10, Exceptional, (269 reviews)
"Great quaint stay on the water. Shower is awesome."
United States
Marianne
The price is AU$128
includes taxes & fees
20 Sept - 21 Sept
Ragged Edge Resort & Marina
A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

11. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (175 reviews)
"We loved sitting in the deck in the evening and again in the morning."
Canada
Molly
The price is AU$380
includes taxes & fees
13 Oct - 14 Oct
Treasure Harbor
A balcony with a view of a beach, a pool, and a thatched-roof structure.

12. Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1,000 reviews)
"Nice pet friendly hotel, clean, nice staff, good continental breakfast."
United States
RAIBEL
The price is AU$246
includes taxes & fees
17 Sept - 18 Sept
Hadley Resort and Marina
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.

13. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,310 reviews)
"Wonderful resort, very friendly staff, would definitely stay again!"
United States
Amy
The price is AU$326
includes taxes & fees
22 Sept - 23 Sept
Amara Cay Resort
A beach with hammocks under palm trees, a sandy beach, and a clear blue sky.

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

Dove Creek Resort & Marina, Trademark Collection by Wyndham
3.0 star property
Key Largo
7.8 out of 10, Good, (1,000 reviews)
"Great place to stay"
United States
Omar Ahmad
The price is AU$185
includes taxes & fees
23 Sept - 24 Sept
Dove Creek Resort & Marina, Trademark Collection by Wyndham
A beach with palm trees, thatched-roof huts, and lounge chairs.

15. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (748 reviews)
"Great resorts - will return again. Highly recommend"
United States
Lourdes
The price is AU$152
includes taxes & fees
17 Sept - 18 Sept
Breezy Palms Resort
A beach with lounge chairs and a blue umbrella, a pier with boats, and a mural of wings on a wall.

16. Drift Hotel

Drift Hotel
2.5 star property
Key Largo
9.0 out of 10, Wonderful, (1,000 reviews)
"Very nice and clean we really enjoyed the private beach as well"
United States
Sheily
The price is AU$163
includes taxes & fees
17 Sept - 18 Sept
Drift Hotel
A wooden dock extending over calm turquoise water, lined with white railings and palm trees.

17. Creekside Inn

Creekside Inn
2.5 star property
Tavernier
7.8 out of 10, Good, (1,016 reviews)
"Great place to stay for the night."
United States
Terry
The price is AU$207
includes taxes & fees
27 Sept - 28 Sept
Creekside Inn

18. Casa Morada

Casa Morada
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (457 reviews)
"The hotel was in the mist of redoing it's landscaping by adding gaint palm trees and some new boat docks, but it didn't interfere with the overall feel of the place. We enjoyed the free paddle boards and pool. Its also located on a beautiful part of the Keys"
United States
Lois
The price is AU$266
includes taxes & fees
6 Oct - 7 Oct
Casa Morada
A poolside area with a water feature, a palm tree, and lounge chairs.

19. Ocean Pointe Suites at Key Largo

Ocean Pointe Suites at Key Largo
3.5 star property
Tavernier
8.4 out of 10, Very good, (1,001 reviews)
"Great place"
United States
Felix
The price is AU$230
includes taxes & fees
30 Sept - 1 Oct
Ocean Pointe Suites at Key Largo
A beachside lounge with a wooden deck, thatched roof, and tropical plants.

20. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
9.0 out of 10, Wonderful, (462 reviews)
"Nice place very clean , quiet . Was great stay for us , thank you"
United States
beata
The price is AU$385
includes taxes & fees
22 Sept - 23 Sept
Bayside Villas by Islander Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windley Key Hotel Reviews

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

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

10/10 Excellent
"We had an excellent stay at Three Waters Resort in Islamorada. Everything about the property was great from start to finish. Our room was very clean, comfortable, and well maintained, and the entire resort was beautiful and inviting. One of the things we really enjoyed was all of the included amenities. We took advantage of the complimentary kayaks, and they also had bikes available for guests to use at no additional charge. It was a great way to get out, explore, and enjoy the area. The fire pits at night were another highlight. Sitting outside by the fire was the perfect way to end the day and really added to the relaxing Keys atmosphere. Overall, we had a fantastic experience. The property was clean, the amenities were excellent, and there honestly wasn’t anything we could complain about. We would absolutely stay at Three Waters again and highly recommend it to anyone visiting Islamorada!"
Eric 2-night trip
Posted 11 hours ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Find out more about Windley Key

Windley Key Lodges information

Number of reviews
10,693
Accommodation
1 Lodges
Lowest Price
AU$128
Highest Price
AU$427

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