Diamond Head Hillside Estate

A Mid-Century-Style Stone Compound at the Foot of Diamond Head

At the foot of Diamond Head, on a private lot of more than 20,000 square feet, this is a new house built to look and live like a mid-century one. The design speaks the language of postwar Hawaii. Low pavilions sit under standing-seam metal roofs with deep eaves for the sun, and walls of basalt stone run from outside to in and back out again. Covered lanais and a planted breezeway do the work of hallways, so you move through the house partly in the open, past a courtyard of ferns and ti. Deep eaves, clerestory windows and cross-ventilation keep the rooms cool.

Inside, the main volume opens up: a vaulted great room lit by clerestory windows, wide-plank oak floors, and a white kitchen built around a long island. Glass-front cabinets hold the household’s own things, and a professional range anchors the cooking. The bedrooms are quieter, with black-framed windows set into white walls, one of them wearing a row of patterned skate decks like art.

Outside, a long pool with a raised spa sits against a bank of banana and monstera, with a cold plunge and a sauna for afterward, an outdoor shower, and a fire pit. A covered outdoor living room, built-in stone bench along one wall, is arguably the best seat on the property. The lawn is flat and wide enough for pickleball, with ping-pong and shuffleboard set up nearby, and the guest house on the far side gives visitors their own front door.

Layout

This vacation home for rent in Diamond Head, Honolulu sleeps up to 10 guests. The main house holds three en-suite bedrooms (two king, one queen) and a powder room, arranged off an open living, dining and kitchen great room, with covered lanais linking the indoor and outdoor rooms. A separate one-bedroom guest house (queen), with its own bath, a living room and a pull-out bed, sits across the grounds for visitors who want their own space.

• Bedroom 1: King, en suite

• Bedroom 2: King, en suite

• Bedroom 3: Queen, en suite

• Bedroom 4: Queen, en suite (guest house)

• Sofa bed in guest house living room

• One guest WC (main house powder room)

Good to know

A 30-night minimum stay applies. Check-in is self-service, with staff on site around the clock to help. Pets are welcome, and assistance animals are always accommodated. Exterior security cameras cover the perimeter of the property only; there are none in the yard or inside the house. Parking is on site and free. The main level of the house is largely single-story, though the grounds are sloped and planted.

Amenities & services

Wifi, dedicated workspace, central air conditioning, ceiling fans, indoor fireplace, fully equipped kitchen, washer, television, piano, gym, sauna, cold plunge, outdoor shower, swimming pool, raised spa, fire pit, covered outdoor living room, outdoor dining area, barbecue grill, pickleball (lawn court), ping-pong table, shuffleboard, solar power with battery storage, two EV chargers, security system, perimeter security cameras, smoke alarm, carbon monoxide alarm, fire extinguisher, first aid kit, on-site parking, self check-in, 24-hour on-site staff, separate guest house, pets welcome

Around

Diamond Head sits right above the house. The state monument’s trail climbs 1.6 miles to a 760-foot summit and the crater’s rim, and it is one of the first things worth doing here. At the foot of the crater, the Kapiolani Community College lot fills every Saturday morning with the KCC Farmers’ Market, Oahu’s oldest, where island growers and cooks (the Pig & the Lady among them) set up at 7:30AM. Kapiolani Park runs down toward the water, the Honolulu Zoo, the Waikiki Aquarium and the Waikiki Shell along its edges. Monsarrat Avenue is the neighborhood’s own strip, family-minded and outdoor: Diamond Head Market & Grill for a quick plate, South Shore Grill for fish tacos after the beach. Kaimana Beach and the calmer Gold Coast shoreline are a short walk or drive, and Waikiki proper begins a few minutes on.