5 Waterfront Retreats from Grand Cayman to the Florida Keys

Along the water’s edge on Old Robin Rd in Grand Cayman’s North Side, Halcyon Point pairs contemporary comfort with purpose-built coastal resilience. Set on a lush 1-acre estate, the fully furnished villa spans five spacious bedrooms and 5.5 elegant bathrooms, framed by sweeping ocean views and a private 200 ft x 40 ft ribbon of white sand beach. Inside, soaring 9’3” ceilings and 8’ solid core doors create an airy, composed atmosphere, while two 16-foot, four-panel panoramic sliding glass doors in the main living and dining areas blur the line between indoors and out. Eight-inch solid block construction and 1”–3” foam insulation layers support energy performance. Upstairs, an expansive sun deck captures sunset light; below, a private pool, spa, and fully equipped outdoor kitchen set the tone for unhurried, open-air days.

With heritage dating to 1996 and a spirit that nods to Old Town’s most celebrated homes, Casa Sapodilla sits beneath the sweeping canopy of its namesake tree in Key West. Broad verandas, intricate trimwork, and warm mahogany floors set a quietly classic tone, while sunlit rooms open through French doors to deep porches. The split-level main house creates an easy sense of privacy: the primary suite rises via its own staircase, and two guest bedrooms ascend another. A detached pool suite with a separate entrance adds welcome flexibility. In the kitchen, custom cabinetry pairs with a new SubZero refrigerator, a refurbished Viking gas range, and generous built-ins. Recent updates include a 2025 metal roof, updated HVAC systems, and a 24 kW Generac whole-house generator. Outside, tropical gardens, stone paths, and soft landscape lighting curve around a heated saltwater lagoon-style pool with natural rock, spa, and cascading waterfalls—just blocks from Duval Street and the Historic Seaport.

Along the water’s edge on E-Lake, one of Miami’s rare recreational lakes, this residence is shaped around a distinctly active waterfront lifestyle—jet skiing, water skiing, sailing, and kayaking, all in accordance with local regulations. Inside, expansive living spaces balance polish and ease, with marble flooring on the main level and warm bamboo hardwood upstairs. The kitchen is tailored for serious cooking, pairing quartz countertops and custom cabinetry with top-tier Miele, Sub-Zero, and Wolf appliances. Outside, daily life naturally spills toward the lake: direct access, a private beach area, a covered lanai for lingering afternoons, and a jacuzzi for unhurried evenings. It’s a setting designed to make indoor-outdoor living feel effortless, with the lake always close at hand.

Along the water’s edge in Toll Gate Shores, this near-new residence brings modern luxury to a relaxed tropical setting in Islamorada. Completed in 2024/2025 by CBT Construction, it offers single-level living with elevator access and three spacious bedrooms and three baths, including two ensuite retreats. At the center, a state-of-the-art kitchen pairs quartz finishes with top-quality appliances, a professional gas range and oven, an ice maker, and expansive cabinetry and counter space, anchored by a generous counter bar designed for easy gathering. Downstairs, a ground-floor enclosure adds approximately 900 square feet of usable space suited to hobbies, workshop needs, and garage areas (exact square footage not warranted). For boating, protected yacht dockage on Hurricane Creek includes a 15,000 lb boat lift and controlled depth of roughly 5–6 feet, depending on tide, plus a swimming pool and access to the owners’ neighborhood park.

Along the Gulf-front in Stirrup Key—one of Marathon’s most exclusive gated communities—this Old Florida Keys fishing lodge pairs classic character with deep-water access and serene open-Gulf vistas. Set across two estate lots totaling 39,500 sf, the property includes an upgraded 165-foot pier dock with six new pilings, where clear water reveals tarpon, angelfish, snapper, nurse sharks, lobsters, and rays beneath the boards. Beautifully maintained and elevated above flood, the residence offers 3 bedrooms, 3 baths, plus a loft suited to a fourth bedroom or home office. Inside, an open-concept great room with massive ceilings and walls of windows frames 180-degree Gulf views, complemented by exposed wood beams and natural stone accents. A screened porch leads to a heated pool tucked behind lush landscaping, with decks and a sandy beach area for sunset evenings.

Price: Contact for pricing