5 Waterfront Escapes from the Florida Keys to St. John

Along the water’s edge on Bogie Channel in Big Pine Key, this open-water retreat is designed for life on the boat and off the clock. An open layout is paired with concrete construction, impact-resistant windows and doors, and a metal roof—practical choices that feel especially considered in a coastal setting. Outside, a 75-foot dock and protected boat basin make coming and going effortless, with direct deep-water access to both the Atlantic and the Gulf. Between outings, a waterfront pool and tropical landscaping frame the home in a lush, easy rhythm, creating shaded moments and sunlit afternoons that unfold naturally along the channel. With two bedrooms and two baths, it reads as a polished boater’s haven where the day’s agenda is set by the tide and the light.

Along the water’s edge in Marathon, this classic Keys waterfront residence pairs relaxed outdoor living with serious boating capability. A private pool and tiki hut set the tone for unhurried afternoons, while a 75-foot concrete dock with a 16,000-lb. lift makes it easy to come and go by water. Deep draft access and quick routes to both the Atlantic and Gulf support everything from day trips to longer runs, all from your own backyard. Inside, the layout spans four bedrooms and three baths—ideal for hosting friends and family without sacrificing privacy. An attached garage adds everyday ease, and an established vacation rental history offers flexibility for those who want a home that can also work while they’re away. Life here revolves around sun, water, and a simple rhythm.

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Along the water’s edge in Saint John, Double Vision pairs a distinctive masonry main house with a separate studio cottage, all set behind a gated entry within a fenced property and surrounded by beautiful gardens. The home’s inverted design places three bedrooms on the ground floor, while the great room rises above—positioned to capture bi-directional, panoramic water views stretching to the southeast and northwest. Upstairs, a covered wraparound porch extends the living space into the breeze. Down below, the bedroom level opens to a large covered porch facing Coral Harbor, creating a quieter waterfront outlook. Inside, the great room is generous and airy with vaulted ceilings, anchored by a well-laid-out kitchen finished in custom mahogany cabinetry and quartz countertops. The private, gated studio cottage adds welcome flexibility for a caretaker or long- or short-term tenant.

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Along the water’s edge in Pompano Beach, this coastal retreat sits directly on the Intracoastal, with the open ocean just shy of 15 minutes away by boat. Set within coveted Cypress Estates, the home pairs everyday comfort with a polished, entertaining-ready layout. Four spacious bedrooms and two luxurious baths support easy living, while an oversized two-car garage keeps gear and vehicles neatly tucked away. Outdoors, a resort-style pool overlooks the Intracoastal, creating a natural backdrop for afternoons in the sun and evenings with friends. A 20-foot-deep water private dock invites spontaneous cruises and longer boating adventures, and it can be doubled to accommodate a larger vessel. Impeccably maintained throughout, the setting makes waterfront life feel effortless from morning to sunset.

Along the water’s edge on a coveted stretch of Summerland Cove Isle, this well-kept residence is set beside crystal-clear, extra-deep flow-through canals. Built of CBS, it pairs a metal roof and fresh exterior paint with travertine floors inside. The layout centers on an open living space, where pocketing sliders dissolve the boundary to a screened porch overlooking the canal—an easy rhythm for mornings with coffee and evenings watching boats glide by. For life on the water, 60 feet of dockage is complemented by boat davits, while covered parking for multiple vehicles and ground-level storage keep gear neatly organized. Just 30 minutes from Key West, the setting offers quick access to world-class fishing and boating, and the everyday ease of the Lower Keys.