Updated on Oct 19, 2026
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Type
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Private vacation home
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Bedrooms
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2
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Bathrooms
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2
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House Rules
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No pets allowed
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Children allowed: ages 0-17 ;Very child-friendly! (See amenities)
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Smoking is not permitted
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No events allowed
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Max Occupancy
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6
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Host Language
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English
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Property Id
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3970025
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"Windley Cottage" is a spotless 2/2.5 Islamorada home located at mile marker 85, away from the highway. It's gated, with a gorgeous pool and private beach from which to launch our kayaks and paddle boards. Whether you’re looking for a couples’ retreat or an exciting Keys experience with the family, this home is the answer!
For a laidback vacation, take a leisurely stroll among the “Bahamian conch style" homes tucked in among lush landscaping. Lounge pool-side with a good book. At sunset, relax with your favorite beverage on our private beach. Then dine at one of the fabulous nearby restaurants, many offering nightly entertainment.
Visit some of the local artist's shops, Robbie's gift shop, or the Rain Barrel. Explore the Windley Key State Geological Site, a former coral rock quarry, where fossils of sea creatures can be seen throughout the park. For a bit more history, stop by the 1935 Hurricane Memorial.
Angler's Reef is centrally located and perfect for exploring all of the Florida Keys! For a day trip, head down Route 1, over the Seven-mile Bridge to Key West and the Southernmost Point in the US.
If you're looking for an adventure packed vacation, start your day with a few laps of our temperature-controlled pool, mere steps from the house. Then paddle out to the sandbar on our complimentary paddle boards or kayaks. After lunch, scuba or snorkel the nearby coral reefs and shipwrecks, rich with underwater wonders. Dive near the popular Alligator Reef Lighthouse, which is visible and easily accessible by boat from Angler's Reef.
After a busy day, enjoy a glass of wine on one of our two private beaches. Play a board game on the back porch. Dim the pendant lights in the great room and turn on the fireplace as you cuddle up to watch your favorite movie after a busy day.
For a fee, dock your boat in our protected lagoon with direct, deep-channel access on the Atlantic. No Boat? Rent a boat or jet skis from one for the local marinas. Book a fishing, scuba, snorkeling charter or party boat at Robbie's.
Fishing is a must, since Islamorada is known as the "Sport Fishing Capital of the World". Whether flats-fishing in the back bays, deep-water fishing for big game, or fishing from our docks, you're sure to have a great experience.
Swim with the dolphins and learn about the local marine life at Theater of the Sea (1/2 mile from our home).
Just 2 miles north is Islamorada Founders Park at MM 87 Bayside. The park offers a shallow water beach, ball fields, playground, fishing jetty, driving cage, 3 paddle ball courts, bocce, tennis, a large playground, basketball courts, an exercise course with 18 stations, and a multi-purpose path within the 40-acre park.
Other municipal parks include the Islamorada Library Beach and Anne’s Beach.
Just pack a few clothes and your toothbrush and head down to the Florida Keys for the vacation of a lifetime in the comfort and luxury of Windley Cottage! See why people from all over the world get sand in their toes and return here again and again!
We offer flexible bed arrangements to meet your group's needs. Call 239-250-4135 for more information.
STR#-24-0163
FL DBPR #DWE5403337
NOTE: We also own a vacation rental property on Cape Cod, MA. Visit Vrbo listing 3757615 for photos and further information of this property.
Located in Islamorada, this vacation home is in the city center and on the beach. History of Diving Museum and Keys History & Discovery Center are cultural highlights, and some of the area's landmarks include Hurricane Monument and Indian Key Historic State Park. Consider Hog Heaven for a night out or MoradaWay Arts & Cultural District if you're traveling with kids. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with hiking/biking trails and ecotours.
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