5 Ultra-Luxury Hawaiian Retreats with Ocean Views and Resort Living

Along Hawaii’s Kona Coast in Kealakekua, Analea Ranch unfolds as a rare retreat shaped by privacy, sustainability, and a sense of place. Set across 25 acres, this off-grid sanctuary is designed for modern self-sufficiency while honoring the timeless charm of old Hawaii. The setting is defined by natural beauty and a feeling of quiet separation from the everyday, with panoramic ocean views that keep the coastline present from morning through dusk. Rich in history, the property reads as more than a destination—it’s an environment where land, light, and legacy take the lead. Days here can move at a slower rhythm: open skies overhead, the ocean always on the horizon, and the enduring calm that comes with a truly independent, intentionally lived landscape.

Along the water’s edge in Kāneʻohe, this exceptional parcel stretches just shy of a full acre from Kaneohe Bay Drive to the ocean. A gentle, park-like slope is framed by breathtaking views of the Koʻolau Mountains and iconic Coconut Island, with no view of the Marine Corps Base to interrupt the natural beauty. A winding driveway passes beneath a canopy of mature trees, setting a private, enchanting tone on arrival. The expansive grounds offer a rare canvas for a world-class custom residence, a resort-style pool, guest accommodations, and outdoor entertaining spaces designed to embrace Hawaiʻi’s indoor-outdoor rhythm. An existing home provides rental income or a place to reside while planning and permitting. Nearby, the Kaneohe Bay Yacht Club adds sailing, tennis, pickleball, live music, family events, and Thursday evening regattas—enjoyable from the property itself. A short drive brings you to Kailua Beach.

Along the South Maui coastline in Wailea, Residence 2802 pairs a fabulous location with breath-taking ocean, island, and coastal views—facing iconic Molokini Island and stretching to Lanai Island. Set on an upper floor, the home’s soaring ceilings and open, airy design create an easy sense of volume and light. Elegant mitered glass bay windows frame the panorama, turning the ever-changing horizon into living artwork. The kitchen and bathrooms have been thoughtfully renovated with modern finishes that balance comfort with a clean, polished feel. A newly added loft introduces welcome flexibility, offering a separate third sleeping area, den, or play room—ideal for shifting needs without disrupting the flow. Here, daily life moves to the rhythm of the water and sky, with every glance drawn outward.

Along the Kona Coast in the prestigious Hualalai Resort, this 1.09-acre homesite offers a rare chance to create a custom luxury estate with uncommon momentum. A complete set of approved architectural plans is already in place, thoughtfully drawn to embrace Hawaiʻi’s celebrated indoor-outdoor lifestyle while taking advantage of the property’s natural beauty. Even better, the offering is permit-ready with all building permits secured—work can begin as soon as crews mobilize, significantly shortening the typical design and permitting timeline and allowing the next owner to move forward with confidence. Ownership also includes the opportunity to apply for membership in the exclusive Hualalai Club, with access to the private Tom Weiskopf-designed Ke’olu Golf Course, the Jack Nicklaus Signature Hualalai Golf Course, the members-only Canoe Club, ocean activities, oceanfront dining, fitness and wellness facilities, tennis, pickleball, spa services, and the renowned Four Seasons Resort Hualalai.

Size: 1.09 acres

Along the water’s edge in Wailea, this highly sought-after Upper Level D plan at Wailea Point pairs a coveted two-level layout with a front-row ocean view. New windows installed in 2022 refresh the residence, including a mitered glass bay window that sharpens the living room outlook and lets the view take center stage. With 3 bedrooms and 4 bathrooms, the design reserves the entire upstairs as a true primary suite, complete with a full bath, soaking tub, and its own private 144 sq. ft. lanai framed by sweeping scenery. Otherwise in original condition, the home offers a rare chance to enjoy Wailea Point as it is—elevated by thoughtful updates, yet ready for a personal touch over time.