5 Waterfront Florida and Caribbean Homes with Skyline Views

Along the water’s edge in Jolly Roger Estates, this one-owner canal-front residence is just 11 years old, beautifully maintained, and truly move-in ready. Elevated and thoughtfully designed, it offers three bedrooms and two bathrooms, with crown molding, tray ceilings, tile showers, and a bright open-concept living area that suits everyday coastal life. A metal roof installed in 2018, along with impact-rated windows and doors throughout, adds comfort and peace of mind. Across the street, a protected salt marsh creates privacy and nightly sunset views with an unspoiled natural backdrop. On the boating side, the free-flowing clear-water canal delivers excellent access to both the ocean and the bay, supported by a private dock with a 7,000-lb side-lift boat elevator. Downstairs, an enclosed angler’s room and full concrete pad keep gear organized for the next day on the water.

On a quiet address in Big Pine Key, this 2020 residence is designed for easy, modern living with a fully furnished interior and an open floor plan that keeps daily routines flowing. Three bedrooms and two baths provide comfortable flexibility, while a dedicated laundry room adds welcome practicality. A metal roof pairs with impact windows and doors for a crisp, durable exterior profile. Outside, a 75-foot concrete dock sits on site, extending the home’s usable space beyond the walls and inviting time spent at the water’s edge. Covered parking and a low-maintenance yard keep upkeep simple, leaving more room in the day for the reasons you live here. It’s a straightforward, well-appointed setting that supports a relaxed Keys rhythm.

A study in contemporary practicality, this multi-family property spans two parcels and is arranged as four units designed for flexible living and income potential. Extensively updated in 2022, it pairs modern electric and plumbing with hurricane-rated windows and doors, plus a brand-new roof—thoughtful improvements that support everyday ease. The mix includes a spacious 3BR/1BA residence, two 2BR/1BA apartments, and a 1BR/1BA unit with remodel potential, inviting a tailored approach to long-term tenancy, short-term stays, or a blend of both. Three kitchens keep each space self-sufficient, while shared laundry adds a simple layer of convenience. Multiple cisterns and separate WAPA meters underscore the property’s functional backbone. Set in Saint Thomas, it’s a versatile setup that can evolve with the way you live and host.

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Along the water’s edge at 950 Brickell Bay Drive, Unit 5205 pairs an urban address with open bay and city views. Set in the heart of Brickell, this beautifully updated residence offers 2 bedrooms and 2 bathrooms arranged around a bright, easygoing layout that suits both quiet mornings and lively evenings in. The outlook does much of the talking here—wide, open vistas that shift from bay calm to the rhythm of the skyline. With its refreshed feel and a location that puts Brickell’s energy close at hand, the home reads as a polished retreat above the everyday. Residents also enjoy access to an array of building amenities, rounding out a lifestyle that balances comfort, convenience, and a front-row perspective on Miami’s waterfront scene.

Along the water’s edge in Hollywood, this 40th-floor corner 2BR/2BA pairs a high-rise vantage with sweeping intracoastal and ocean views. Floor-to-ceiling windows pull in abundant natural light, while a wraparound balcony frames sunrise-to-sunset panoramas—an easy rhythm for morning coffee and late-day unwinding. Offered fully furnished and move-in ready, the residence keeps daily living effortless, whether you’re here full-time or arriving for a getaway. The full-service amenity building extends the experience with a pool, fitness center, concierge, and beach service, creating a seamless, resort-like routine. Flexible ownership allows you to live, vacation, or rent short-term for income potential, balancing lifestyle and versatility in one elevated setting.