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

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb
No exact matches found, but these alternatives could be just right

Recommended hotels in Windley Key

A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.

1. 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, (307 reviews)
"Great place to stay!"
United States
Liosbel
The price is AU$435
includes taxes & fees
29 Nov - 30 Nov
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A beachside patio with white furniture, palm trees, and a thatched umbrella.

2. Drop Anchor

Drop Anchor
3.0 star property
Islamorada
8.6 out of 10, Excellent, (1,000 reviews)
"Everything was nice and clean. I enjoyed my stay there."
United States
Leydis
The price is AU$214
includes taxes & fees
3 Nov - 4 Nov
Drop Anchor
A covered outdoor area with a white railing, a white table, and white plastic chairs.

3. Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (304 reviews)
"Excellent stay! Love this place and will definitely be back!"
United States
Hailey Ritch and Patrick
The price is AU$270
includes taxes & fees
3 Nov - 4 Nov
Coconut Cove Resort and Marina
A beachfront hotel with a pool, beach chairs, and a view of the ocean at sunset.

4. Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.2 out of 10, Very good, (1,002 reviews)
"Very clean very quiet Close to nice restaurants and bars"
United States
Jose
The price is AU$290
includes taxes & fees
29 Nov - 30 Nov
Fisher Inn Resort & 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, (34 reviews)
"Very friendly staff"
United States
Maria
The price is AU$298
includes taxes & fees
16 Nov - 17 Nov
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
9.4 out of 10, Exceptional, (1,808 reviews)
"Nice beach walkable property Great breakfast made to order"
United States
kent brian
The price is AU$302
includes taxes & fees
3 Nov - 4 Nov
Chesapeake Beach Resort
A bathroom with a large bathtub, a view of the sea, and a pier with boats.

7. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,501 reviews)
"Great place. Phenomenal food!"
United States
Brandon
The price is AU$394
includes taxes & fees
29 Nov - 30 Nov
Cheeca Lodge & Spa
A resort with a pool, multiple buildings, and a waterfront view.

8. 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, (1,006 reviews)
"The view, the property amenities and room are great! Had a great time!"
United States
ruben
The price is AU$202
includes taxes & fees
17 Nov - 18 Nov
Dove Creek Resort & Marina, Trademark Collection by Wyndham
A beach with palm trees, lounge chairs, and a clear view of the ocean.

9. Hampton Inn Key Largo Manatee Bay

Hampton Inn Key Largo Manatee Bay
2.5 star property
Key Largo
8.8 out of 10, Excellent, (1,124 reviews)
"Great stay"
United States
Joliene
The price is AU$209
includes taxes & fees
30 Nov - 1 Dec
Hampton Inn Key Largo Manatee Bay
A beach hut with a thatched roof, surrounded by lounge chairs and a picnic table, overlooking a calm sea.

10. Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,201 reviews)
"cute nice place in an incredible spot. Will visit there again for sure."
United States
keith
The price is AU$144
includes taxes & fees
15 Nov - 16 Nov
Rock Reef Resort
A row of motel rooms with blue lighting, a picnic table, and bicycles parked outside.

11. Drift Hotel

Drift Hotel
2.5 star property
Key Largo
9.0 out of 10, Wonderful, (1,004 reviews)
"Excellent location"
United States
kelly
The price is AU$147
includes taxes & fees
3 Nov - 4 Nov
Drift Hotel
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.

12. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,324 reviews)
"Great location as well."
United States
Amir
The price is AU$354
includes taxes & fees
15 Nov - 16 Nov
Amara Cay Resort
A balcony with a view of a beach, palm trees, and a clear sky.

13. Sunset Cove Beach Resort

Sunset Cove Beach Resort
2.5 star property
Key Largo
9.2 out of 10, Wonderful, (1,006 reviews)
"Very nice clean hotel with friendly staff."
Canada
Alexey
The price is AU$187
includes taxes & fees
2 Dec - 3 Dec
Sunset Cove Beach Resort
A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.

14. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,004 reviews)
"Loved the beach area! Bed was comfortable, kitchenette well appointed, and there were enough electrical outlets!"
United States
Jane
The price is AU$240
includes taxes & fees
4 Nov - 5 Nov
La Jolla Resort
A balcony with a view of the sea, a table, and two chairs.

15. Waterside Suites & Marina

Waterside Suites & Marina
3.5 star property
Key Largo
9.0 out of 10, Wonderful, (1,517 reviews)
"Nice location. Relaxing stay. Pet friendly."
United States
Marco
The price is AU$218
includes taxes & fees
3 Nov - 4 Nov
Waterside Suites & Marina
A covered outdoor area with a wooden deck, palm trees, and a view of the beach.

16. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (777 reviews)
"Such a great place to stay!!"
United States
Gavin
The price is AU$184
includes taxes & fees
3 Nov - 4 Nov
Breezy Palms Resort
A patio with a wooden table and chairs, a sofa, and a striped ottoman. There are palm trees and a view of the beach.

17. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,160 reviews)
"The entire resort was clean, staff very friendly, bar and restaurant and pools were fabulous! Would definitely stay there again!"
United States
DEBORAH
The price is AU$475
includes taxes & fees
3 Nov - 4 Nov
Islander Resort
A balcony with a view of a river, a wooden cabinet, and a door leading to a shower.

18. Creekside Inn

Creekside Inn
2.5 star property
Tavernier
7.8 out of 10, Good, (1,017 reviews)
"Can’t wait to go back"
United States
Markevus
The price is AU$220
includes taxes & fees
2 Dec - 3 Dec
Creekside Inn
Terrace/patio

19. Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.4 out of 10, Exceptional, (1,563 reviews)
"Very friendly staff, quiet and low key if that’s what you’re looking for"
United States
Mark Blair
The price is AU$262
includes taxes & fees
3 Nov - 4 Nov
Lime Tree Bay Resort
A beach with rows of sun loungers and palm trees.

20. Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
2.5 star property
Islamorada
9.6 out of 10, Exceptional, (277 reviews)
"Incredible place, ample room and everything you need to cook and to bbq."
United States
Nathalie
The price is AU$225
includes taxes & fees
18 Nov - 19 Nov
Ragged Edge Resort & Marina
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

Cheeca Lodge & Spa

Cheeca Lodge & Spa

8/10 Good
"Nice resort. Beautiful surroundings and pools. Food was good. Very noisy a/c units making balconies unsuitable to sit in peace. All small buildings seem to have the same issue. Obvious lack of sufficient staff in general."
Francois 3-night trip
Posted less than an hour ago
Cheeca Lodge & Spa

Find out more about Windley Key

Windley Key Cottages information

Number of reviews
12,646
Accommodation
32 Cottages
Lowest Price
AU$144
Highest Price
AU$475

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