A Private Hillside Estate Near Diamond Head
Welcome to Diamond Head Hillside Estate, a remarkable private retreat nestled within one of Honolulu's most desirable residential settings. Offering nearly 5,900 square feet of thoughtfully designed indoor-outdoor living space—including an elegant detached guest house spanning an additional 960 square feet—this expansive estate blends sophisticated island living with exceptional wellness and recreation amenities. Surrounded by lush tropical landscaping and designed for extended stays, Diamond Head Hillside Estate is an extraordinary sanctuary for families, friends, and remote professionals seeking privacy, comfort, and the best of Oʻahu living.
Created to embrace Hawaiʻi's year-round climate, the estate seamlessly connects spacious interiors with beautifully landscaped outdoor spaces. Soaring ceilings, abundant natural light, and thoughtfully curated furnishings create an atmosphere that is both refined and welcoming, while resort-inspired amenities transform every stay into a memorable island experience.
Living Spaces
The expansive great room serves as the heart of the home, where dramatic 14-foot ceilings and oversized windows fill the interiors with natural light while framing views of the surrounding tropical gardens. Warm finishes, custom built-ins, and elegant furnishings create inviting spaces designed for gathering, entertaining, or simply unwinding after a day exploring Honolulu.
The open-concept layout flows effortlessly from the living room to the dining area and covered lanai, creating a seamless connection between indoor comfort and outdoor island living. Whether hosting family dinners or enjoying quiet mornings surrounded by lush greenery, every space has been thoughtfully designed to encourage relaxation and connection.
Sleeping Accommodations | Up to 10 Guests
Diamond Head Hillside Estate offers four beautifully appointed bedroom suites across the main residence and detached guest house, providing generous accommodations with exceptional privacy and flexibility.
• Primary Suite
The spacious primary suite features a king-size bed and a luxurious en-suite bathroom, creating a peaceful retreat designed for comfort and relaxation.
• Guest Suite Two
Elegantly furnished with a queen-size bed, this inviting bedroom includes a private en-suite bathroom and tranquil surroundings for restful nights.
• Guest Suite Three
Featuring a queen-size bed and a private en-suite bathroom, this comfortable guest room offers both privacy and convenience.
• Detached Guest House Suite
Ideal for extended family or guests seeking additional privacy, the detached guest house features a king-size bedroom with a dedicated bathroom, along with a spacious private living room.
• Additional Sleeping Space
The guest house living room includes a full-size sleeper sofa, providing flexible accommodations for additional guests.
Gourmet Kitchen & Dining
The spacious chef's kitchen is thoughtfully designed for both everyday living and effortless entertaining. Generous preparation space, open sightlines, and convenient access to the dining room and outdoor living areas allow guests to remain connected while preparing everything from casual breakfasts to memorable family dinners.
The adjoining dining area naturally extends to the covered lanai, creating a welcoming environment for indoor meals, alfresco dining, and evenings spent enjoying Hawaiʻi's gentle trade winds.
Resort-Style Outdoor Living
The outdoor living spaces have been thoughtfully designed as a private wellness retreat surrounded by lush tropical landscaping.
• Resort-style swimming pool
• Private hot tub and invigorating cold plunge
• Outdoor fire pit with comfortable gathering spaces
• Covered lanais for outdoor dining and lounging
• Home sauna and outdoor shower
• Dedicated home fitness center
• Unofficial pickleball court
• Ping pong table and shuffleboard
• Beautifully landscaped tropical gardens offering exceptional privacy
Whether beginning the day with a workout, cooling off in the pool, relaxing in the sauna, or gathering around the fire pit beneath the stars, every outdoor space has been designed to celebrate Hawaiʻi's relaxed indoor-outdoor lifestyle.
Location
Diamond Head Hillside Estate enjoys a private setting in one of Honolulu's most desirable residential neighborhoods, offering both peaceful seclusion and convenient access to the island's renowned beaches, shopping, dining, and outdoor recreation. Ideally positioned near the iconic Diamond Head area, guests can easily experience the best of Oʻahu while returning each day to the comfort and tranquility of their own private retreat.
From scenic coastal walks and world-famous beaches to championship golf, local markets, and cultural attractions, the estate provides an exceptional home base for discovering everything Honolulu has to offer during an extended island stay.
Good to Know
- Diamond Head Hillside Estate is offered exclusively for stays of 30 nights or longer. Rates are based on a full 30-day reservation. Please inquire for availability and additional details.
- Pets may be considered on a case-by-case basis and are subject to owner approval and applicable fees.
- Exterior security cameras monitor only the perimeter of the property. No cameras are located inside the residence or within the private outdoor living areas.
- Additional conveniences include central air conditioning throughout, a dedicated home office within the guest house, two electric vehicle charging stations, solar panels with battery backup, generous storage, and a comprehensive home security system.
Diamond Head Hillside Estate combines sophisticated island design, exceptional wellness amenities, and expansive indoor-outdoor living to create a one-of-a-kind Honolulu retreat where luxury, privacy, and the spirit of Hawaiʻi come together for unforgettable extended stays.
