5 Island Retreats and Oceanview Condos Across Hawaii

Along a country dirt road makai of the Road to Hana, 210 Door of Faith Rd. offers a rare canvas in Huelo for those drawn to a quieter side of Maui. The 2.64-acre parcel is mostly clear and thoughtfully varied—flat at the front, then gently sloping to the back—framed by a sea of greenery with grass and trees throughout, and the Pacific Ocean nearby. A current structure sits on the land and will need remodeling, yet practical groundwork is already in place, with plumbing lines under the home replaced in recent years. Water is supplied by a private well on the property, supporting an independent, rural lifestyle. With privacy, peacefulness, and room to reimagine what’s here, the setting invites a slower, more intentional everyday rhythm.

Size: 2.64 acres

Along the water’s edge on Alii Drive in Kailua Kona, this one-of-a-kind oceanfront unit sits in one of the closest-to-the-ocean positions on the island, pairing sweeping water views with the steady rhythm of waves. Approved for Short-Term Vacation Rental (STVR), it’s offered turnkey furnished and move-in ready, with thoughtful completeness: all-new linens and pillows, dishes and glassware, pots and pans, cutlery and flatware, a coffee pot, knife set, and even pictures and decorative items. Recent updates keep the interior crisp, including fresh paint and brand new stove and refrigerator, while windows and doors (approx. 2014), cement board siding (2017), and exterior paint (2024) underscore ongoing care. Two parking areas with a garage add everyday ease, and access is simple with only three stairs to the unit.

Price: Contact for pricing

Commanding views from a high floor in Prospect Tower Apts, this rarely available three-bedroom residence sits at the top of Ward Ave with a front-row outlook over the city, Diamond Head, the ocean, and even fireworks. Wood floors anchor the living room and draw you toward a large, breezy lanai—an easy extension of daily life. Inside, recent upgrades include split A/C and an updated primary bath vanity, while an extra half bath with a washer/dryer adds welcome practicality. The generously appointed kitchen stands out for its abundant cabinets and drawers, a thoughtful luxury in condo living. In a well-managed, secure building with high owner occupancy and 100% hurricane insurance, amenities range from a pool and barbecue area to gardens, plus an extra storage locker on the same floor—making everyday routines feel notably effortless.

Rising above Waikiki on the 29th floor of Diamond Head Vista, this fully furnished residence is defined by panoramic views spanning the ocean, Diamond Head, the city, and the mountains. Beautifully updated throughout, the interior pairs an open-concept kitchen with luxury vinyl flooring and motorized retractable shades that quietly refine the everyday. The 1-bedroom, 1-bath layout includes a custom-tiled shower, adding a crisp, tailored finish. Outside, a private lanai becomes an effortless extension of the living space, cooled by island breezes and enhanced with new motorized wind-shades—ideal for lingering over the scenery from morning light to evening glow. With world-class beaches, dining, and shopping just moments away, the experience here is equal parts high-floor calm and vibrant city energy.

Along the lush Hamakua Coast near Hakalau, this rare botanical retreat offers a gentle way to live on the land now while planning what comes next. A thoughtfully designed tiny house provides comfortable on-site living amid fertile, mature plantings that read like a private sanctuary. Meandering natural streams and tranquil water pools thread through the acreage, bringing a soft soundtrack of flowing water and an everyday connection to the landscape. The setting is rich, green, and alive—well suited to gardening, tending orchards, or simply moving at East Hawaii’s unhurried pace. Mature, fruiting trees include tangerine, durian, mountain apple, coconut, lime, mango, lychee, mangosteen, starfruit, cacao, longon, and clove. Mornings arrive with ocean-cooled breezes, birdsong, and filtered light through the canopy, inviting a simpler rhythm.

Size: 3.63 acres