Drop Anchor Resort And Marina

Located at Mile Marker 85 on picturesque Windley Key in Islamorada, Drop Anchor is a classic Florida Keys vacation lodge and boutique marina offering old-Florida charm with modern comforts. This waterfront retreat is ideal for family vacations, fishing trips, and tropical reunions, drawing guests who want easy access to both laid-back island life and world-class boating.

Drop Anchor offers a selection of waterfront lodging and limited dockage for boats up to 30 feet—perfect for center consoles, bay boats, and skiffs from brands like Sea Hunt, Cobia, and Boston Whaler. The marina operates daily from 8:00 AM to 6:00 PM and provides essential amenities such as water and electric hook-ups, fish cleaning stations, and trailer parking.

Guests are just minutes from Islamorada’s legendary attractions, including Theater of the Sea, History of Diving Museum, and the famous sandbar near Whale Harbor. Local shopping includes Rain Barrel Village for quirky art and souvenirs, while dining options range from the upscale Chef Michael’s to the family-friendly Islamorada Fish Company and Lorelei Restaurant & Cabana Bar—ideal for sunset cocktails.

Drop Anchor is more than a place to dock—it’s a relaxed, palm-fringed escape where you can grill out by the pool, mingle with fellow travelers, and make the Florida Keys feel like home.