5 Island and Oceanfront Retreats in St. John and Florida Keys

Set along one of St. John’s most coveted waterfront points, this extraordinary private estate presents over 800 feet of pristine shoreline and unparalleled access to the Caribbean Sea. A private dock creates effortless connection to the water, while sweeping vistas span the Virgin Islands National Park and extend toward the British Virgin Islands, revealing spectacular sunrises and sunsets. The residence features four king suites, a generous bunk room, and beautifully designed indoor and outdoor living areas ideal for sophisticated entertaining and relaxed island living. A professional chef’s kitchen and butler’s pantry provide the perfect setting for catered occasions and unforgettable gatherings. Two secluded beaches, manicured lawns, and a panoramic pool enhance this exceptional retreat where privacy, natural splendor, and adventure come together. A rare opportunity to own a timeless Caribbean legacy property.

Along the waterfront in Chocolate Hole, Still Waters and Ripple present a rare two-residence setup with flexible living and rental potential. Ripple is a beautifully remodeled 2 bedroom, 2 bath masonry home with Hart Bay and Chocolate Hole views, paired with completely separate road access for privacy and ease. Above it, Still Waters sits off a different road, offering the same vistas from a higher place on the property. The current owner’s focus on detail and maintenance shows in added solar, power walls, and new furnishings—supporting a very successful 6-figure income-producing 3 bedroom, 2 bath masonry pool villa. With over $700,000 in improvements and remodeling, the property is designed to accommodate living in one home while renting the other long term or short term, all while honoring existing Still Waters rental reservations.

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Along the water’s edge on Plantation Island in Duck Key, this 2019 residence pairs solid concrete construction with a calm, contemporary sense of ease. More than 3,100 square feet unfold into four bedrooms, a dedicated office/den, and 3.5 bathrooms, with spacious living areas designed to welcome natural light and support everything from lively entertaining to quiet evenings after a day on the water. The primary suite is oriented to beautiful ocean views, adding a restorative backdrop to everyday routines, while the flexible office/den adapts effortlessly to remote work or additional guest accommodations. Outside, a private backyard oasis channels the Florida Keys lifestyle with a brand-new swimming pool and hot tub, a putting green for quick practice, and a fully equipped outdoor kitchen with an entertaining area made for long, lingering gatherings.

Along the water’s edge in Fort Lauderdale, this direct oceanfront condo pairs turnkey, fully furnished living with a balcony that stretches to just over 1,000 square feet—one of the largest in South Florida. Ten-foot ceilings add to the airy feel, while a washer and dryer in the unit keeps daily routines effortless. Both bedrooms enjoy ocean views, and the building is pet friendly for an easy, lock-and-leave lifestyle. Two covered garage parking spaces and additional storage round out the practical details. Amenities are designed for unhurried days: a heated pool with ocean views and cabanas, a fitness center, BBQ grill, and kitchen area, plus cable and internet. With 600 feet of private beach and Lauderdale-By-The-Sea’s beach restaurants and shops within walking distance, mornings and evenings can naturally revolve around the shore.

Along the water’s edge in St. Quaco and Zimmerman, Double Vision is a unique masonry residence with a gated entry and fully fenced grounds, framed by beautiful gardens and bi-directional water views. An inverted layout places three bedrooms on the ground floor, while the great room is elevated upstairs to capture panoramic vistas to the southeast and northwest. On the upper level, a covered wraparound porch extends the living space outdoors; below, a large covered porch faces Coral Harbor for quieter moments close to the water. Inside, the great room feels open and airy with vaulted ceilings, anchored by a well-laid-out kitchen featuring custom mahogany cabinetry and quartz countertops. A separate studio masonry cottage, set apart with its own gate, offers privacy and flexibility for a caretaker or long- or short-term tenant, shaping a lifestyle that balances retreat and possibility.

Price: Contact for pricing