Diamond Head Hillside Estate**
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Settle into the heart of the home, where soaring ceilings, natural light, and garden views create an inviting space to gather, relax, and reconnect.
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From leisurely breakfasts to family dinners, the spacious kitchen island and open dining area make every meal feel effortlessly social.
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Challenge friends to a game of ping pong or enjoy a little friendly competition in this bright, thoughtfully designed recreation space.
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Open the wall of glass and let island living take over. The great room flows seamlessly onto the lanai and tropical gardens beyond.
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Surrounded by lush greenery, the private pool offers a refreshing retreat for sunny afternoons, quiet mornings, and post-adventure relaxation.
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Whether you're reading, catching up on work, or enjoying a quiet conversation, this comfortable sitting area provides a peaceful place to unwind.
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Gather with family and friends in this light-filled great room, where the kitchen, dining area, and living spaces come together with effortless flow.
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Designed for connection, the soaring great room offers comfortable seating, abundant natural light, and seamless access to the covered lanai beyond.
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Framed by oversized windows and tropical greenery, the kitchen brings the beauty of the outdoors into everyday moments.
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Thoughtful craftsmanship and curated design elements add warmth, character, and a sense of home throughout the residence.
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Find a quiet corner to enjoy your morning coffee, catch up on a favorite book, or simply take in the peaceful garden surroundings.
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Wake to tropical garden views and gentle island light in this serene bedroom retreat, thoughtfully designed for rest and relaxation.
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Wake each morning to tropical garden views and soft natural light in this peaceful bedroom retreat, thoughtfully designed for comfort and relaxation.
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Surrounded by lush greenery just beyond the windows, this inviting bedroom offers a quiet place to unwind after a day in Honolulu.
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Natural light, calming finishes, and garden views create a restful sanctuary designed for slow mornings and restorative evenings.
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Start and end your day in this bright, spa-inspired bathroom featuring clean design, natural light, and a spacious walk-in shower.
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Thoughtfully appointed with modern finishes and a walk-in shower, this serene bathroom offers both comfort and convenience.
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Refresh and recharge in the spacious walk-in shower, where simple, elegant design creates a calming spa-like experience.
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Begin your day with garden views and natural light in this spacious primary bathroom, thoughtfully designed with a soaking tub and a calming, spa-inspired atmosphere.
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Clean lines, warm finishes, and generous counter space make this beautifully appointed bathroom both functional and inviting.
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A quiet retreat within the home, this comfortable sitting area offers the perfect place to read, relax, or enjoy a peaceful moment between adventures.
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Thoughtfully designed custom cabinetry and built-ins provide abundant storage while complementing the home's clean, contemporary aesthetic.
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Refresh after a swim or simply enjoy one of island living's simple pleasures in this private outdoor shower surrounded by tropical landscaping.
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Natural textures, tropical greenery, and contemporary architecture come together to create a welcoming outdoor space that feels both private and serene.
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Relax in the shade of the spacious covered lanai, where comfortable seating and tropical surroundings create an inviting setting for conversation and quiet afternoons.
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Designed for effortless indoor-outdoor living, this covered gathering space offers a comfortable place to enjoy morning coffee, evening cocktails, and time together.
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A beautifully designed covered walkway welcomes you home, blending warm natural materials, tropical landscaping, and contemporary island architecture.
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Framed by lush greenery and clean architectural lines, the entry creates a warm and memorable first impression from the moment you arrive.
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Tucked among tropical plantings, this peaceful corner invites you to slow down, relax, and enjoy the tranquility of the surrounding gardens.
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Lush landscaping and thoughtful design come together to create a welcoming arrival experience that feels private, refined, and distinctly Hawaiian.
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Enjoy a friendly match on the property's unofficial pickleball court, surrounded by tropical gardens and the relaxed atmosphere of island living.
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Lush tropical foliage and thoughtfully curated gardens create a sense of privacy and tranquility throughout the estate.
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Contemporary design, mature landscaping, and a peaceful residential setting come together to create an inviting island retreat.
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Surrounded by vibrant greenery, the property's beautifully landscaped grounds offer space to relax, explore, and enjoy the outdoors.
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Expansive lawns and tropical plantings provide a serene backdrop for outdoor gatherings, recreation, and quiet moments in the sunshine.
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From its lush gardens to its thoughtfully designed outdoor spaces, this private Honolulu estate offers an exceptional setting for extended island stays.
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Expansive green space, mature tropical landscaping, and a private residential setting create a peaceful outdoor retreat in the heart of Honolulu.
Wake up to soaring ceilings, lush tropical gardens, and the effortless flow of island living at Diamond Head Hillside Estate. Tucked within a private Honolulu setting, this thoughtfully designed luxury estate offers nearly 5,900 square feet of beautifully appointed indoor-outdoor living space, including an exceptional collection of wellness and recreation amenities, and a detached guest house spanning an additional 960 square feet. Whether you're gathering with family, working remotely for an extended stay, or simply seeking room to unwind, this distinctive holiday home delivers comfort, privacy, and a true sense of place.
What You'll Love About Diamond Head Hillside Estate
• Nearly 4,900 square feet of thoughtfully designed indoor living space
• Resort-style outdoor retreat with pool, hot tub, cold plunge, and fire pit
• Detached guest house with private living room, office, and additional sleeping accommodations
• Wellness-focused amenities including a home gym, sauna, and outdoor shower
• Recreation features including an unofficial pickleball court, ping pong table, and shuffleboard
Living & Dining
The main residence is defined by its soaring 14-foot ceilings, abundant natural light, and seamless connection to the outdoors. Expansive gathering spaces invite conversation and relaxation, while oversized windows frame views of the surrounding tropical landscape. Custom built-ins, warm finishes, and carefully curated furnishings create an atmosphere that feels both elevated and welcoming.
The open-concept great room flows effortlessly into the dining area and covered lanai, making it easy to move between indoor entertaining and outdoor living throughout the day.
Chef-Ready Kitchen
At the heart of the home, the spacious kitchen is designed for everything from casual breakfasts to memorable dinners with family and friends. Open sightlines keep everyone connected while generous prep space and convenient access to the dining and outdoor areas make entertaining effortless.
Outdoor Oasis
Designed for year-round enjoyment, the outdoor spaces feel like a private retreat. Spend sunny afternoons cooling off in the sparkling pool, soak in the hot tub beneath swaying palms, or recharge in the cold plunge after a workout or sauna session.
Covered lanais provide comfortable spaces for morning coffee and evening gatherings, while the fire pit creates the perfect setting to linger outdoors after sunset. Mature landscaping surrounds the property, adding privacy and a tranquil backdrop to every moment.
For guests who enjoy staying active, the property also features an unofficial pickleball court, ping pong table, shuffleboard, and a dedicated outdoor shower.
Sleeping Quarters
• Primary Suite: Spacious private suite with en-suite bathroom and king bed
• Bedroom 2: Ensuite guest bedroom with queen bed
• Bedroom 3: Ensuite guest bedroom with queen bed
• Detached Guest House Bedroom: Private bedroom with dedicated bathroom, complete with a king bed
• Detached Guest House Living Room: Full-size sleeper sofa for additional guests
Extras
• Central air conditioning throughout
• Dedicated home gym
• Private sauna
• Office workspace in the guest house
• Security system
• Two electric vehicle charging stations
• Solar panels and battery backup system
• Generous storage throughout the property
Nearby
Nearby beaches, dining, shopping, and attractions can be added once the neighborhood or district is confirmed.
Good to Know
• Pets are considered on a case-by-case basis. Subject to a fee determined at the time of the request.
• Exterior security cameras monitor the perimeter of the property only. There are no cameras within the home or private yard areas.
• This residence is offered exclusively for 30-day rental periods. Rates are based on a full 30-day stay. Please inquire for availability and details.
• Ideal for families, couples traveling together, and digital nomads seeking an extended Hawaii stay
• TAT ID: TA-177-407-7952-01
• TMK / Parcel ID: 1310200080000
From morning workouts and poolside afternoons to evenings gathered around the fire pit, Diamond Head Hillside Estate offers the space, privacy, and elevated comforts that make longer stays in Honolulu feel effortless. Reserve your dates and settle into island living at its finest.
Entertainment
Amenities
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Internal Amenities
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| Room | Beds | Amenities |
| Primary Bedroom |
King (1)
|
Ensuite Bathroom, Garden View, Central A/C, Ceiling Fan, Ceiling Fan |
| Guest Bedroom 2 |
Queen (1)
|
Ensuite Bathroom, Garden View, Central A/C, Ceiling Fan |
| Guest Bedroom 4 |
Sofa Bed (1)
King (1)
|
Ensuite Bathroom, Guest House, Full Sofa Bed, Central A/C, Ceiling Fan, Blackout Drapes |
| Guest Bedroom 3 |
Queen (1)
|
Ensuite Bathroom, Garden View, Central A/C, Ceiling Fan |
| Primary Bedroom Ensuite | ||
| Guest Bedroom 2 Ensuite | ||
| Guest Bedroom 3 Ensuite | ||
| Guest Bedroom 4 Ensuite | ||
| Powder Room 1 |