View All Diamond Head HI Homes with Guest House Listings
First open house 7/26/2026 from 1:30 - 5:00. Exceptional views, exceptional house!! Rare opportunity to make this coveted combination your home! Sweeping ocean views incl...
- 5 Beds
- 3 Baths
- 202613575 MLS
- FS - Fee Simple Tenure
- 5 DOM
Most homes trade elevation for the view—climb higher, live farther from everything. This Halekoa Drive home rewrites that story: nearly 180 degrees of open ocean and Diam...
- 5 Beds
- 3 Baths
- 202611287 MLS
- FS - Fee Simple Tenure
- 23 DOM
OPEN HOUSE-SUNDAY 06/28/26 - 2-5pm! PRICE JUST REDUCED! Conveniently located near Kahala Mall, this beautiful property sits on a 12,117 approx sqft lot with a spacious 3...
- 4 Beds
- 4 Baths
- 202610571 MLS
- FS - Fee Simple Tenure
- 57 DOM
Located in the desirable Kapahulu neighborhood, this single-family home sits just one block from Monsarrat Avenue, known for its vibrant mix of eateries and coffee shops....
- 3 Beds
- 2 Baths
- 202607777 MLS
- FS - Fee Simple Tenure
- 56 DOM
Unique and so very special, this 1937 Albert Ives home nestled between Diamond Head Rd and the world famous Diamond Head National Monument. This beautiful home is locate...
- 4 Beds
- 5 Baths
- 202524617 MLS
- FS - Fee Simple Tenure
- 39 DOM
****Newer Price!!!***** Rarely available Haleloa II. Great floor plan, peek-a-tinyboo of ocean, good sized storage next to the parking stalls, two covered parking stal...
- 3 Beds
- 2 Baths
- 202516953 MLS
- FS - Fee Simple Tenure
- Haleloa 2 Bldg.
- 283 DOM
Luxury Estate at The Pointe on Hawaii Loa Ridge. Nestled within the private double-gated community of The Pointe, this magnificent residence boasts six bedrooms and seven...
- 6 Beds
- 8 Baths
- 202510488 MLS
- FS - Fee Simple Tenure
- 90 DOM
Location!Location!Lovation...Imagine owning a beachfront home with 8 bedrooms and 6 bathrooms in an incredibly convenient location – a truly rare find! This spacious resi...
- 6 Beds
- 7 Baths
- 202511169 MLS
- FS - Fee Simple Tenure
- 333 DOM
Nestled in a private gated community of just 24 residences, this beautifully renovated 3-bedroom, 2.5-bath home offers stunning views of the ocean and Diamond Head. The o...
- 3 Beds
- 3 Baths
- 202427168 MLS
- FS - Fee Simple Tenure
- Kahala Pacifica Bldg.
- 75 DOM
Charming island home in the heart of Kahala! This large 4 bedroom, 3 bath home has been renovated and features high ceilings, split ACs, a new kitchen and bath, and upgra...
- 4 Beds
- 3 Baths
- 202324088 MLS
- FS - Fee Simple Tenure
- 73 DOM
Classic island living on a desirable street Aukai Avenue. This luxurious single leveled Kahala property features a Main House with 5-BDRM/5-BATH and a separate Guest Suit...
- 6 Beds
- 6 Baths
- 202406542 MLS
- FS - Fee Simple Tenure
- 150 DOM
Rarely available Kalaniiki Estates 3 bedroom 2 bath! Each unit is a fully separate house but it's in a project where all of the maintenance of the grounds and amenities ...
- 3 Beds
- 2 Baths
- 202408764 MLS
- FS - Fee Simple Tenure
- Kalani Iki Estates Bldg.
- 42 DOM
Rarely available and ready for your personal touch! This beautiful single level oceanfront home sits on a larger level lot, which allows for a lifestyle we all dream abou...
- 3 Beds
- 4 Baths
- 201800900 MLS
- FS - Fee Simple Tenure
- 2608 DOM
The house with a fantastic view is a solid concrete and steel structure and every architectural system is flawlessly well built. It combines the ambiance of Hawaii with c...
- 4 Beds
- 4 Baths
- 202313921 MLS
- FS - Fee Simple Tenure
- 129 DOM
Discover all the details about this beautiful home in Kahala Kua. Highly desirable 2 story home sitting on a level lot with a spacious floor plan offering ease of moveme...
- 4 Beds
- 4 Baths
- 202403084 MLS
- FS - Fee Simple Tenure
- 168 DOM
Welcome to the private gated community of Nohona Kahala. Nohona Kahala is situated in an ideal location, offers luxurious living spaces, presents peace of mind security, ...
- 3 Beds
- 3 Baths
- 202400833 MLS
- FS - Fee Simple Tenure
- 328 DOM
*PRICED BELOW TAX ASSESSED VALUE* This classic 1920s home restored and well cared for many years, has a timeless elegance and charm that you won't forget. Nestled amongst...
- 4 Beds
- 5 Baths
- 202306789 MLS
- FS - Fee Simple Tenure
- 529 DOM
Based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on . Information is deemed reliable but not guaranteed. Copyright: 2026 by HiCentral MLS, Ltd. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Diamond Head, HI · Curated MLS Search
Homes with Guest House in Diamond Head, HI
An editorially curated view of every active homes with guest house listing in Diamond Head, HI. Updated in real time from the local MLS, presented without the noise.
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