5 Luxury Hawaiian Retreats from North Shore Sands to Kapalua Views

Steps from the shoreline on Oahu’s North Shore, this custom-built residence fronts the expansive white sands of Ke Iki Beach along the famed seven-mile stretch. A reverse floor plan places the living, kitchen, and dining areas upstairs, joined by an office and a spacious covered lanai—positioned to take in ocean views and trade winds. Downstairs, three bedrooms include a suite with a separate entrance and full bath, plus two additional baths, a den, and direct access out to the beach. Thoughtful modern comforts include tinted windows, split A/Cs, and 20 photovoltaic panels, all within desired Flood Zone X. Outside, landscaped grounds unfold in grassy areas with flowering plants, fruit trees, and palms, along with an enclosed rinse-off after surf or sand. Days end naturally with seasonal sunsets and winter swells just beyond the door.

Commanding views from near the top of a private cul-de-sac within the gated enclave of Wailea Kialoa, this two-level residence is oriented to sweeping Pacific sunsets and serene Haleakala mountain views. Beautifully reimagined for seamless indoor-outdoor living, it pairs expansive Fleetwood sliding doors with multiple lanais designed for unhurried entertaining. Outdoors, a resort-style heated pool and spa set the tone, joined by an outdoor bar and theater, gas tiki torches, and architectural lighting that extends evenings well past dusk. A photovoltaic system supports daily living, while 24-hour gated security adds peace of mind. The primary suite is conceived as a private sanctuary, complete with a sauna, gym, and an indoor-outdoor spa shower. Just minutes from Wailea’s beaches, dining, and championship golf, days here naturally unfold between sun, sky, and open air.

Beyond the gate at 76-863 N Pakalakala Pl in Kailua Kona, this custom legacy estate offers a tranquil retreat just minutes from town. Set at an approximate 950-foot elevation on 1.11 landscaped, fully irrigated acres, the setting is defined by manicured tropical gardens and an easy sense of privacy. Inside, the great room centers on a custom lava rock gas fireplace with a Koa mantle and built-in shelving, while solid ohia hardwood and distinctive travertine floors run throughout. The large custom kitchen pairs granite countertops with Sub-Zero, Viking, and Bosch appliances. Four bedrooms and three baths are joined by an office, laundry room, ample closets and storage (including an attic), plus a screened-in auxiliary room. Large covered lanais frame coastline and village views, extending daily life outdoors.

Along the water’s edge at Kaanapali Beach, this 9th-floor private ownership condo at Kaanapali Alii pairs a landmark, hotel-zoned setting with a view that stretches across the ocean and sandy golden shoreline. Positioned over the tranquil inner courtyard and pools of this legacy visitor property, the residence is described as beautifully appointed and rarely available in this prime placement. A generous 200 sq ft lanai becomes the natural gathering spot—made for morning coffee, winter sun, and long, unhurried evenings as sunsets unfold over the water. Come winter, whale watching adds a daily rhythm to the horizon. Offered as a turnkey Maui residence, it’s a refined way to experience life at the center of Kaanapali Beach, with the sea always in view.

Along the north side of the famed Ritz-Carlton Resort, Suite 1221-23 pairs a spacious two-bedroom, two-bath layout with sweeping outlooks over Honolua Bay and the West Maui mountains. Designed as a flexible “lock-off,” it can be enjoyed as a fully equipped one-bedroom residence and a separate studio hotel room—ideal for balancing privacy, hosting, and rental options. Ownership opens the door to the resort’s extensive amenities, from The Ritz Spa with private garden showers, volcanic stone grottos, steam rooms, saunas, and a movement studio with ocean views, to concierge service, a fitness center, shopping, meeting spaces, restaurants, and the Jean-Michel Cousteau Ambassadors of the Environment program. Beyond the hotel, Kapalua Resort’s 22,000 acres unfold into golf, tennis, hiking paths, beaches, and open space, setting an easy rhythm for Maui living.