Discover Your Dream Vacation at Windley Cottage in Anglers Reef, Islamorada, Florida Keys
Discover Your Dream Vacation at Windley Cottage in Anglers Reef, Islamorada, Florida Keys
Discover Your Dream Vacation at Windley Cottage in Anglers Reef, Islamorada, Florida Keys
Discover Your Dream Vacation at Windley Cottage in Anglers Reef, Islamorada, Florida Keys
Discover Your Dream Vacation at Windley Cottage in Anglers Reef, Islamorada, Florida Keys
Discover Your Dream Vacation at Windley Cottage in Anglers Reef, Islamorada, Florida Keys
Fishing/Docks
Oceanside Pool
Oceanside Pool
Oceanside Pool
Oceanside Pool
Oceanside Pool
Entertainment
Oceanside Pool
Entertainment
Welcome to Our Home
Amenities
Views
Quaint gated community
Heated Pool
Boat Slips (for a fee)
3 Decks and a Balcony
Complimentary WiFi
Electric Fireplace/Heater
Free Dedicated Parking for Two Vehicles
Excellent location
Fast deep-water access
Kayaks/ Paddle boards
Flexible Bedding
Tropical Landscaping
Grill for Deck Dining
Photo Gallery
Our resort-style pool provides ample chairs, loungers, tables, and umbrellas as well as rest rooms.
Windley Cottage Guest Reviews
10/10 Excellent
Beth H.
Jan 26, 2026
We had a very nice stay at Windley Cottage. Roger & Linda were very nice to work with. They responded quickly to all our questions before our trip and checked in with us during our stay to make sure we had everything we needed.
10/10 Excellent
Kat A.
Apr 4, 2026
We loved our stay here! Our kids loved the big pool, the views were beautiful, these cottages are very cute and plenty of room. Definitely perfect for renting a boat. We will definitely come back!!
10/10 Excellent
Emily C.
Apr 26, 2025
We had such a nice time at the Windley Cottage. The owners effectively communicated information about the home and check in before the stay, making arrival very easy. The home was very clean and had everything that we needed. The Anglers Reef area was nice and quiet. We enjoyed walks to the docks, kayaking, and swimming in the pool. We absolutely loved Islamorada and hope to visit again!
Location - Mile Marker 85.3 on Windley Key
Windley Cottage
129 Anglers Way Islamorada, FL 33036 (239) 250-4135 (239)248-0862