5 Elevated Hawaiian Retreats from Kailua to South Maui

From its elevated setting on Kalaheo Hillside, 445 Iliwahi Loop feels like a private retreat thoughtfully tuned to indoor-outdoor living. A considered, full renovation brings vaulted ceilings, an open great room, and walls of glass that look out to the pool, gardens, and fountains, with easy flow to expansive covered lanais. The chef’s kitchen anchors daily life with a Viking range, Sub-Zero refrigeration, and a generous island connecting seamlessly to dining and living areas. Two private primary suites add flexibility for multigenerational living or a dedicated guest wing, while two separate office/dens support work-from-home rhythms. The spa-inspired primary bath features a soaking tub and oversized shower. Outside: mature palms, a garden gazebo, and covered seating set the scene for golden-hour gatherings and dusk swims.

Along the water’s edge in Kapolei, this elegant end-unit villa pairs a legal short-term rental setup with a polished, lived-in sense of style. As the largest 2-bedroom floor plan, it’s designed for easy hosting, with a layout that supports indoor/outdoor lounging and dining. Beautiful ocean views and tropical breezes flow through every room, framed by three lanais oriented to the East, South, and West. Meticulously upgraded by the original owners, the interiors are layered with elegant antiques, tropical furnishings, local artwork, and Indich wool area rugs. Recent updates include newly varnished travertine floors, renewed countertops, deep polished bathroom doors, a new washer and dryer, and upgraded designer mattresses, linens, and bedding. Two deeded parking spaces complete the offering, ready for an effortless handoff with existing bookings in place.

Set just off coveted Polipoli Road in Kula, this Upcountry estate carries an artistic lineage that feels inseparable from its setting. Once home to celebrated Hawai‘i artist and educator Richard “Dick” L. Nelson—creator of the renowned Tri-Hue watercolor technique—the property reflects a life shaped by creativity, tranquility, and a deep connection to place. Architectural pedigree is woven into the narrative, grounding the home’s presence in thoughtful design rather than trend. Here, the pace of Upcountry Maui comes forward: quiet mornings, open skies, and the kind of natural surroundings that invite reflection and focus. With its rare blend of legacy and landscape, the estate reads as both a personal retreat and a living tribute to the inspiration that has long defined Kula.

From its elevated setting at The Masters Kaanapali Hillside in Lahaina, Condo 603 unfolds as a rare, private retreat with sweeping ocean, golf course, and year-round sunset views. Set within one of the community’s most coveted low-density buildings—just four residences total—it feels quietly removed, privately positioned at the lower end of the complex in a cooler, more tranquil pocket framed by lush tropical landscaping. Inside, a beautifully renovated, turnkey interior has been thoughtfully redesigned with high-end finishes throughout: premium flooring, granite countertops, GE appliances, spa-inspired Kohler shower systems, and designer fixtures. Abundant natural light carries through the living spaces, while seamless indoor-outdoor living is enhanced by an automatic exterior shade. Days here move easily between calm interiors and a horizon that never stops changing.

Steps from the shoreline at Keawakapu Beach, Hale Hui Kai offers boutique oceanfront living in one of South Maui’s most desirable settings. Set on the ground floor, this beautifully remodeled 2-bedroom, 2-bath residence balances clean comfort with thoughtful materials, from bamboo cabinetry to granite countertops and other quality finishes. A spacious lanai extends the living space outdoors, capturing a glimpse of the ocean and inviting unhurried mornings after a walk on the white sands just beyond. Hotel zoning and vacation-rental eligibility add flexibility, whether envisioned as an island retreat, a second home, or an income-producing investment. With dining, shopping, and golf minutes away in Kihei and greater South Maui, daily life here can stay as active—or as quiet—as you choose.