Key Lime Sailing Club & Cottages

The proposition is unusual enough to spell out: you rent a cottage on the bayside of Key Largo, and a sailboat comes with it. The condition is the one a sensible owner would set. Private use of the 22-foot Catalina docked on site is included for qualified sailors with recent time on the water, at no charge; there is no certification to show, but there is a conversation about experience. Kayaks, canoes, paddleboards, snorkeling gear, fishing tackle, and bicycles are included as well, under a stated no-hidden-fees policy. Want something bigger or different to sail? Other boats are available for a fee. For a sailing family, that changes the arithmetic of a Keys week entirely: the boat is at the dock behind the cottage, and Florida Bay starts at the seawall.

Not everyone in a group sails, and the operation plans for that. Captained snorkel trips and sunset cruises run aboard its larger sailing catamaran and a crewed yacht, so the non-sailors get out on the water too.

The water is the other half of the argument. The bayside of the Upper Keys is shallow, protected, and scattered with mangrove islands, forgiving water for rusty skippers and honest water for learning, which is why American Sailing Academy teaches the ASA courses on site. Come as a beginner, leave with the certification and a week of unsupervised practice behind it; there are worse curricula.

The repeat-guest culture tells you what the place is. The operation says it has guests on their tenth consecutive year and more, and it carries a TripAdvisor Travelers’ Choice award and Airbnb Superhost status. It is cottages, boats, and the bay, run for people who think that is the whole point.