Windley Cottage, Anglers Reef, Islamorada Florida

08/29/2026

We just revamped our website. Take a look at:
www. windleycottage.com

Discover luxury at Windley Cottage, Anglers Reef Islamorada - your perfect vacation rental in the Florida Keys! Book now!

03/05/2025

We still have good availability from May 31st-the end of the year, including all holidays except New Year’s week. So give us a call to reserve your desired week.

08/10/2024

Great prices for Indian Summer stays!No Service Fees if you book directly through us.

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04/12/2024

Our 2/2.5 Islamorada home is the perfect vacation home for any season! Temperature-controlled pool, dock, private beach from which to launch our kayaks and paddle boards. Walk to exceptional restaurants. Our location is convenient to everywhere in the Keys. No matter what water sport you want, the Keys has it!

About this property OCEANFRONT ANGLERS REEF LUXURY HOME- Pool, Dock, Beach, Kayaks, Paddle Boards "Windley Cottage" is a private home in the small gated community of Angler's Reef in Islamorada. This welcoming, tastefully-decorated home is located at mile marker 85, away from the highway , and just....

02/25/2024

Come vacation in Islamorada! We have a 2/2.5 home with pool, dock, and beach. Launch our kayaks and paddle boards from the beach and get out to the Islamorada Sandbar fun. Check us out and give us a call to book directly! www.windleycottage.com

02/15/2024

Our new venture in Mashpee, Cape Cod is available as of March 16th and is available every week until August 2nd at this time. Check it out and book directly through us if you'd like to save the fees.

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02/15/2024

Several Summer weeks available at both of our homes. Availability in Islamorada home from April 6th.

About this property OCEANFRONT ANGLERS REEF LUXURY HOME- Pool, Dock, Beach, Kayaks, Paddle Boards "Windley Cottage" is a private home in the small gated community of Angler's Reef in Islamorada. This welcoming, tastefully-decorated home is located at mile marker 85, away from the highway , and just....

01/10/2024

Check out our newest venture in the New Seabury area of Cape Cod. Now accepting bookings.

11/01/2023

Soon, you'll be able to stay with us in a second location! How does it sound to summer in Cape Cod and winter in Islamorada? Yes, in 2 weeks we are buying a place in "The Mews" in New Seabury. Walk to a beautiful beach on Nantucket Sound. We will post photos as soon as we have it ready for you!

08/12/2023

Just returned from a relaxing week at Windley Cottage. Walked around the grounds every evening and hung out at the pool every afternoon.