Windley Key Cottages

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

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Recommended hotels in Windley Key

1. Fisher Inn Resort & Marina

Islamorada

Alexandra

P9,801 total

includes taxes & fees

Sep 21 - Sep 22

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

Islamorada

Eslita

P18,645 total

includes taxes & fees

Sep 23 - Sep 24

3. Drop Anchor

Islamorada

Marianela

P10,659 total

includes taxes & fees

Sep 23 - Sep 24

4. Coconut Cove Resort and Marina

Islamorada

Jasmine

P10,515 total

includes taxes & fees

Sep 20 - Sep 21

5. The Ocean View Inn & Pub

Islamorada

Maria

P13,147 total

includes taxes & fees

Sep 22 - Sep 23

6. Chesapeake Beach Resort

Matecumbe

Suresh

P14,188 total

includes taxes & fees

Sep 20 - Sep 21

7. La Jolla Resort

Matecumbe

Tamara

P9,503 total

includes taxes & fees

Sep 28 - Sep 29

8. Ragged Edge Resort & Marina

Islamorada

Nathalie

P5,296 total

includes taxes & fees

Sep 20 - Sep 21

9. Cheeca Lodge & Spa

Matecumbe

RAIBEL

P15,103 total

includes taxes & fees

Sep 30 - Oct 1

10. Islander Resort

Matecumbe

Sonia

P19,891 total

includes taxes & fees

Sep 30 - Oct 1

11. Breezy Palms Resort

Matecumbe

Lourdes

P6,407 total

includes taxes & fees

Sep 30 - Oct 1

12. Treasure Harbor

Islamorada

Molly

P17,015 total

includes taxes & fees

Oct 17 - Oct 18

13. Amara Cay Resort

Matecumbe

Amy

P15,496 total

includes taxes & fees

Sep 30 - Oct 1

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

Key Largo

Omar Ahmad

P8,277 total

includes taxes & fees

Sep 24 - Sep 25

15. Drift Hotel

Key Largo

Sheily

P7,322 total

includes taxes & fees

Sep 24 - Sep 25

16. Hadley Resort and Marina

Matecumbe

Pang

P11,585 total

includes taxes & fees

Sep 30 - Oct 1

17. Rock Reef Resort

Rock Harbor

Tia

P7,138 total

includes taxes & fees

Sep 24 - Sep 25

18. Bayside Villas by Islander Resort

Matecumbe

beata

P18,049 total

includes taxes & fees

Sep 30 - Oct 1

19. Creekside Inn

Tavernier

Terry

P10,099 total

includes taxes & fees

Sep 20 - Sep 21

20. Seafarer Key Largo

Rock Harbor

Susan

P7,960 total

includes taxes & fees

Sep 24 - Sep 25

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Top Windley Key Hotel Reviews

Chesapeake Beach Resort

10/10 Excellent

"Everything about the Chesapeake resort is perfect ,had the most incredible time ,will definitely return !!!"

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!"

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