5 Golf, Island, and Historic Retreats in Florida and Exuma

From its elevated setting in Weston Hills, this residence captures wrap-around golf and lake views spanning the 16th and 17th holes of the Tour Course. Set on 0.29 acres at the end of a quiet cul-de-sac within the boutique enclave of The Fairways, it’s approached by a long paver drive framed by high privacy hedges. Inside, nearly 3,600 square feet under air unfolds beneath soaring 20-foot ceilings, where floor-to-ceiling hurricane-protected windows draw in abundant natural light and the meandering water beyond. Brand new sliding impact glass doors in the primary bedroom, family room, and living room deepen the indoor-outdoor connection. The downstairs primary suite pairs a sitting room with a double-sided marble fireplace, plus a spa-like bath ensuite, while a fourth bedroom is configured as an office with custom solid-wood built-ins. Upstairs, two generous bedrooms share a spacious bath, continuing the home’s calm, considered flow.

Along the water’s edge on Big Pine Key, this beautifully maintained concrete block home pairs comfort with easygoing Keys living. Inside, a spacious living room flows into the dining area, where triple sliding glass doors open to a screened patio—an ideal spot to take in the coastal breeze and tranquil water views. The kitchen brings everyday practicality with stainless steel appliances and granite countertops, while impact windows and sliders throughout add peace of mind. Offered fully furnished, including kayaks, it’s ready for life on the canal from day one. Boating is equally seamless, with a 12,000 lb boat lift and excellent access just minutes to Pine Channel and open water for fishing, diving, or cruising turquoise Florida Keys waters. Days here naturally begin and end outdoors, with serene salt pond views as the backdrop.

In the heart of Old Town Key West, this fully renovated, light-filled historic home offers the rare flexibility of a legal duplex while preserving an easy, lived-in sense of charm. Modern updates meet old-world character across two spacious levels, each arranged with 2 bedrooms, 1 bathroom, and a full kitchen anchored by an open-concept living, kitchen, and dining area. The layout invites a range of rhythms—keep one unit for yourself and rent the other, or open the entire home for a more expansive retreat. Downstairs, the lower unit extends naturally outdoors, opening to a deck and pool that set the scene for quiet mornings and unhurried evenings. It’s a place designed to live simply, with the bonus of built-in income potential.

Along the water’s edge in the City of Key Colony Beach, this well cared for full duplex has been owned by the same family for more than 40 years and is set on a picturesque 100-foot-wide canal. Timeless updates and exceptional dockage shape daily life here, with 75 feet total to accommodate larger vessels—42 feet on the south side (261) and 33 feet on the north side (271). Boaters will appreciate the quick access to both the open Ocean and the open Gulf, just a short five-minute ride, or a peaceful 10-minute paddle. Inside, the full duplex offers 4 bedrooms and 4 bathrooms with inviting living space designed for gathering and unwinding. Ample parking for cars and trailers is paired with a covered carport and storage room on the south side. Days unfold easily by strolling or biking to the marina, golf course, courts, and Sunset Park.

Along the water’s edge in gated February Point Resort on Great Exuma, this town house is designed for unhurried, view-filled days. A landscaped front yard leads to a covered staircase and an ample pergola-style covered patio, furnished for entertaining or quiet afternoons outdoors. Inside, the ground floor is arranged for easy living with two bedrooms, two bathrooms, laundry facilities, and an open sequence of living and dining room alongside the kitchen. Upstairs, a king bedroom suite adds a separate walk-in closet and a grand bathroom with a jetted tub, walk-in shower, and his-and-hers sinks. A shared storage house sits just east of the villa. Community amenities include Rusty Anchor restaurant, a marina, gym, tennis/pickleball court, two pools, three beaches, and the Sapphire Beach Club spa—close to the highlights of George Town, yet serene.