5 Hawaii Retreats with Ocean Views, Lanais, and Acreage

From its elevated setting in Wailuku’s Kehalani master-planned community, this thoughtfully transformed residence frames serene ocean and Haleakala mountain views while offering an unexpected sense of privacy. Designed with gatherings in mind, the home centers on a super-sized, extra-large covered lanai with Trex flooring, opening from the family room to a sprinklered backyard with a wide lawn—made possible through a retaining wall and added fill—and convenient side-gate access. Downstairs, engineered hardwood floors run through the living room, dining area, and family room. The kitchen balances function and polish with an island for bar-stool seating, granite counter-tops, a new Bosch dishwasher, a double-oven range, refinished cabinets, and porcelain tile floors. Upstairs, three bedrooms and two remodeled bathrooms continue the view-filled calm, with Mitsubishi split air-conditioning in the primary bedroom and downstairs.

From its elevated setting in Waikoloa, this thoughtfully designed single-level retreat frames panoramic mountain vistas by day and sunset ocean views by evening. A custom layout embraces the rhythms of Hawai’i, with an open-concept floor plan that lets indoor and outdoor living blend naturally for both entertaining and everyday ease. At the center, a chef’s kitchen pairs premium appliances with a spacious walk-in pantry, a built-in beverage refrigerator, and a 120-bottle wine cooler—details that make hosting feel effortless. Rich mahogany cabinetry runs throughout, complemented by Cali bamboo flooring in the living areas and tile flooring in the kitchen and baths. Practical comforts are equally considered, including an owned photovoltaic system with battery storage and a whole-home central vacuum system. Life here is defined by light, flow, and the steady presence of the landscape.

Set on 8.852 acres in the Manawai Subdivision, this CPR property pairs a peaceful country setting with sweeping ocean views on Maui’s North Shore. Located on the ocean side of Hana Highway, it offers a rare blend of privacy and usable land, fully fenced and currently home to sheep and chickens for an easygoing farm-and-ranch rhythm. Equestrian enthusiasts will appreciate the existing horse riding arena, while the CPR designation allows for construction of a 1,500-square-foot cottage and barn—supported by an active building permit already in place. The setting keeps daily life close to Haiku Town’s cafés, restaurants, and shopping, with Ho‘okipa Beach Park and historic Paia Town nearby for surf culture, galleries, dining, and Mana Foods. Here, the days can unfold outdoors, with room to shape a retreat that feels distinctly your own.

Size: 8.852 acres

Within the gated enclave of The Villas at Kehalani in Wailuku, this two-story Plan 3 townhome is shaped by cool mountain breezes funneled from nearby Iao Valley and wide panoramas that stretch from Haleakala’s sunrise-kissed peaks to Kahului Harbor’s shimmering expanse. Inside, a soaring 20-foot living room ceiling and oversized door draw in natural light, while expansive indoor-outdoor living opens to a serene covered lanai. Upgrades and eco-friendly features include a high-end 20-SEER AC system with ionizing filtration, vented roofs, radiant barriers, Low-E windows, and drought-resistant native landscaping. The gourmet island kitchen pairs African Teak cabinetry with Energy Star stainless steel appliances and granite countertops, and the ground floor living area is finished in premium bamboo flooring. A first-floor primary suite with a bath featuring glass block inserts offers privacy and ease, with exterior upkeep handled by the complex for low-maintenance living.

Rising above Koloa, this peaceful top-floor corner retreat turns daily life into a series of framed vistas. Every window captures a postcard view: lush mountain scenery from the guest room, ocean blues from the living room, and coastal beauty from the master bedroom. A vaulted ceiling adds volume and light, and paired with corner-unit windows, the interiors feel brighter, taller, and more open than a standard layout. The kitchen is fully updated and stocked, while fresh, welcoming furnishings keep the atmosphere easy and relaxed. Step onto the lanai for sunset views, rainbows after passing showers, and winter whale sightings. With a strong track record of bookings and consistently exceptional reviews from returning visitors, it’s a space designed for calm mornings and unhurried evenings.