5 Luxury Hawaiian Retreats with Sweeping Oceanfront Views

Along the ocean’s edge in Koloa, Whalers Cove offers a boutique approach to waterfront living, defined by its intimate scale—just 39 condos in the community. The property’s unique design and the gentle curvature of its buildings are more than an architectural gesture; they’re purposeful, orienting every residence toward the water. As a result, each condo is “pointed towards the ocean,” framing postcard views as a daily backdrop rather than an occasional treat. The setting feels considered and cohesive, with the site’s direct oceanfront location doing much of the talking. Here, the rhythm of the day is shaped by light on the water and a constant visual connection to the shoreline—an experience that feels quietly special, morning to evening.

Down a winding road that traces a dramatic cliffside, 21 Hulumanu Place sits within Maluhia Country Ranches—named for “maluhia,” or peace and tranquility, for good reason. Inside the main house, light pours through soaring ceilings as views open in every direction, with a lanai that draws daily life outdoors. The layout includes three bedrooms, three baths, a lofted bonus space, and a kitchen designed for those who love to cook and gather. An attached studio adds flexibility, while a detached two-bedroom cottage expands the sense of retreat with jaw-dropping views of its own. Set on over 2.6 acres and agriculturally zoned, the land offers room to imagine what a quieter, more spacious rhythm could become.

From its elevated crest on a quiet cul-de-sac in Maui Meadows, this half-acre South Maui estate frames unobstructed ocean, Haleakala, Molokini, and outer-island views with a rare sense of privacy. The main residence offers three spacious en-suite bedrooms, a gourmet custom kitchen finished in rich Koa wood cabinetry, and elegant parquet flooring. Vaulted ceilings and motorized skylights draw in natural light and breezes, while wrap-around lanais and an expansive wrap-around deck extend daily living outdoors. Beyond the home, a private professional-grade tennis court and an 11-foot-deep custom pool—accented with sculptures—set the tone for resort-like afternoons. Zen-inspired Japanese gardens with koi ponds and stone bridges invite quiet wandering, with a large art studio and outdoor shower adding to the easy, creative rhythm of the property.

Along the Kona coastline in a small, gated subdivision, this custom Feduik-built home is set on over half an acre with flawless ocean and coastline views. Designed for Hawaii-styled living, the layout emphasizes an easy indoor-to-outdoor rhythm, anchored by a large covered lanai that extends daily life into the open air. A private courtyard creates a sense of arrival and offers thoughtful separation for visitors: each guest suite includes its own personal entrance from the courtyard, along with direct access to the main home. The result is a residence that balances togetherness and privacy with uncommon ease. From morning light over the water to evenings spent under the lanai, the setting and flow invite an effortless, view-forward way of living in Kailua Kona.

Along the water’s edge on Honolulu’s Gold Coast, Diamond Head Apartments presents a rare chance to reimagine a classic residence within an iconic oceanfront building designed by Vladimir Ossipoff and set along the slopes of world-famous Diamond Head. Inside, the condominium offers the building’s largest floor plan, with generous interior space and an existing layout that serves as a solid foundation for thoughtful updates. Sweeping views stretch from ocean to mountain, while excellent cross-ventilation invites cooling trade winds through the home—an everyday luxury in itself. A designer kitchen is already in place, featuring Poliform cabinetry, a Gaggenau range, Bosch appliances, and a custom stainless steel island, offering a polished starting point for a tailored renovation. It’s an architectural gem ready to be restored into a personal retreat.