Diamond Head, HI · Curated MLS Search
Homes with Guest Room in Diamond Head, HI
An editorially curated view of every active homes with guest room listing in Diamond Head, HI. Updated in real time from the local MLS, presented without the noise.
Browse Active ListingsDiamond Head Market — Homes with Guest Room Comparison
Live MLS data — Diamond Head vs. Homes with Guest Room
Homes with Guest Room in Diamond Head: Market Data
Data as of (MLS snapshot; listings below update live)
KEVIN PEDERSEN | RS-77808's review of MLS data as of October 20, 2026 shows 10 active listings for Diamond Head homes with guest room. That is about 5% of the 209 active listings in Diamond Head across every property type. At the time, 1 more was pending, and 15 sold in the past six months.
| Measure | Value |
|---|---|
| Active listings | 10 |
| All active listings in Diamond Head, every property type | 209 |
| Under contract | 1 |
| Sold, past six months | 15 |
Homes with Guest Room in other areas
- Honolulu: 158 active, median $799,000
- Ewa Beach: 18 active, median $757,500
- Hawaii Kai: 14 active, median $794,500
- Aiea: 9 active
- Kailua: 8 active
Market questions
How many Diamond Head homes with guest room are for sale?
There were 10 Diamond Head homes with guest room for sale as of October 20, 2026, based on KEVIN PEDERSEN | RS-77808's review of MLS data.
How do Diamond Head homes with guest room stack up against other areas?
As of October 20, 2026, there were 10 Diamond Head homes with guest room for sale. In the same search, Honolulu had 158 homes with guest room for sale at a median list price of $799,000, Ewa Beach had 18 homes with guest room for sale at a median list price of $757,500 and Hawaii Kai had 14 homes with guest room for sale at a median list price of $794,500.
How many Diamond Head homes with guest room sold in the past six months?
15 Diamond Head homes with guest room sold in the six months before October 20, 2026.
How many Diamond Head homes with guest room are pending?
As of October 20, 2026, 1 listing for Diamond Head homes with guest room was under contract.
How do Diamond Head homes with guest room compare with all active listings in Diamond Head?
As of October 20, 2026, there were 10 Diamond Head homes with guest room for sale, out of 209 active listings in Diamond Head across every property type.
Listing data courtesy of HiCentral MLS, Ltd.
Next Steps in Diamond Head, HI
View All Diamond Head HI Homes with Guest Room Listings
One of the most coveted views on all of Oahu. Unobstructed panoramic ocean views stretch from Koko Head to Diamond Head. Immaculate, ultra-modern, custom-designed estate ...
- 4 Beds
- 4 Baths
- 202619607 MLS
- FS - Fee Simple Tenure
- 5 DOM
Welcome to a wonderful residence at Regency Park. This well-maintained two-bedroom, two-bath condo unit is on the top floor of Building 1, where morning sun and greenery...
- 2 Beds
- 2 Baths
- 202618876 MLS
- FS - Fee Simple Tenure
- Regency Park Bldg.
- 20 DOM
From the moment you arrive, you’ll sense what sets this exceptional home apart. Designed and built as a 100% custom residence offering approx 4100 sq ft of living space, ...
- 5 Beds
- 4 Baths
- 202614948 MLS
- FS - Fee Simple Tenure
- 24 DOM
Executive modern home with panoramic Ocean Views! The flagstone driveway welcomes you to this home featuring an open floor plan with the Living area, Kitchen and Dining ...
- 4 Beds
- 4 Baths
- 202617360 MLS
- FS - Fee Simple Tenure
- 46 DOM
Welcome to Regency Park! Motivated and ready to sell this rarely available 3 bedroom 2 bath home with over 1200 sq ft of living with treetop views of the canal in the pre...
- 3 Beds
- 2 Baths
- 202611462 MLS
- FS - Fee Simple Tenure
- Regency Park Bldg.
- 72 DOM
Welcome to this beautifully reimagined ‘Aina Haina residence, where spacious design, quality upgrades, and breathtaking natural surroundings come together in one exceptio...
- 6 Beds
- 4 Baths
- 202613952 MLS
- FS - Fee Simple Tenure
- 88 DOM
**BACK ON MARKET, NO FAULT OF SELLER + PRICE ADJUSTMENT!** Rarely available condo with its own private yard/garden area- an uncommon find in Honolulu condo living! Pet-fr...
- 2 Beds
- 2 Baths
- 202614239 MLS
- FS - Fee Simple Tenure
- Regency Park Bldg.
- 94 DOM
Exceptional views, exceptional house!! Rare opportunity to make this coveted combination your home! Sweeping ocean views include views of Waialae Golf Course and Diamond ...
- 5 Beds
- 3 Baths
- 202613575 MLS
- FS - Fee Simple Tenure
- 37 DOM
New construction on .41 acres along Kahala Avenue, this 7,741 sq ft residence was designed around light, water and the art of entertaining. Walls of glass rise to soaring...
- 5 Beds
- 8 Baths
- 202612088 MLS
- FS - Fee Simple Tenure
- 115 DOM
The Paiko Retreat stands as a true Architectural Masterpiece after a comprehensive restoration. Sitting on over an acre of mature landscaping, Kanewai Spring, waterfalls,...
- 5 Beds
- 7 Baths
- 202611456 MLS
- FS - Fee Simple Tenure
- 132 DOM
Welcome to Regency Park! This fee simple 2-bedroom, 2-bathroom high-rise unit offers 802 sq ft of interior living space plus 129 sq ft of lanai/patio area—perfect for ind...
- 2 Beds
- 2 Baths
- 202611469 MLS
- FS - Fee Simple Tenure
- Regency Park Bldg.
- 73 DOM
You will want to see this extensively renovated & restored single family home in the Wilhelmina Rise neighborhood! Enjoy the Kaimuki vibe & easy access to town, restaura...
- 4 Beds
- 4 Baths
- 202610932 MLS
- FS - Fee Simple Tenure
- 83 DOM
Move right into this beautifully updated East Oahu townhome, perfectly situated near beaches, parks, and everyday conveniences. Thoughtfully updated with modern comfor...
- 2 Beds
- 2 Baths
- 202610828 MLS
- FS - Fee Simple Tenure
- Kuliouou Kai Villa Bldg.
- 44 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
With gorgeous views of the deep blue Pacific Ocean, you will fall in love with this third-floor condo, located only one unit back from the ocean front in one of the most ...
- 2 Beds
- 2 Baths
- 202606626 MLS
- LH - Leasehold Tenure
- Kahala Beach Bldg.
- 62 DOM
Located just one lot from the blue Pacific Ocean, this Diamond Head residence offers sunset views and easy access to ocean activities. A deeded interest in a private beac...
- 5 Beds
- 4 Baths
- 202605403 MLS
- FS - Fee Simple Tenure
- 37 DOM
Hidden gem in Kaimuki. Ready to move-in or rent out. Enjoy the cool Tradewind breezes, the beautiful treetop garden & mountain views, and the Eastern Morning sunrises, wi...
- 2 Beds
- 2 Baths
- 202605298 MLS
- FS - Fee Simple Tenure
- Regency Park Bldg.
- 58 DOM
Fabulous Honolulu location in desirable hillside community of Wilhelmina Rise is this sophisticated multi-level home with 4-bedrooms, 2.5 baths. The main level features a...
- 4 Beds
- 3 Baths
- 202605202 MLS
- FS - Fee Simple Tenure
- 73 DOM
***Seller is open to provide 'Closing Cost Credit of $17,000*** to allow Buyer to renovate the flooring, bathroom and kitchen. Welcome home to Regency Park located bel...
- 2 Beds
- 2 Baths
- 202603965 MLS
- FS - Fee Simple Tenure
- Regency Park Bldg.
- 90 DOM
Located in the desirable Kuliouou/east Honolulu neighborhood, this substantial mid-century home presents a unique opportunity for those seeking space, versatility, and lo...
- 8 Beds
- 4 Baths
- 202604120 MLS
- FS - Fee Simple Tenure
- 97 DOM
Direct Oceanfront apt in one of the most desirable, luxurious buildings on the Gold Coast overlooking famous surf spot from living area, and Diamond Head from each bedroo...
- 2 Beds
- 2 Baths
- 202603618 MLS
- FS - Fee Simple Tenure
- 3003 Kalakaua Bldg.
- 258 DOM
RARE garden apartment in a low-rise building with its own enclosed tropical garden and lanai. Enjoy a cool, east-facing, PET-FRIENDLY 3-bedroom, upgraded 2-full-bath w/2 ...
- 3 Beds
- 2 Baths
- 202603540 MLS
- FS - Fee Simple Tenure
- Regency Park Bldg.
- 258 DOM
Discover a gem of a property in vibrant Kapahulu, ideally located near Waikiki, Diamond Head, Kapiolani Park, dining, and world-class beaches. This versatile home (2 stru...
- 3 Beds
- 2 Baths
- 202600268 MLS
- FS - Fee Simple Tenure
- 63 DOM
HUGE PRICE DECREASE. Amazing location on the slope of Diamond Head and across from La Pietra, Kapiolani Park and the Gold Coast beaches. Uniquely designed, this rarely av...
- 3 Beds
- 3 Baths
- 202600677 MLS
- FS - Fee Simple Tenure
- Queens Court At Kapiolani Bldg.
- 120 DOM
Well-maintained 2-bedroom, 2-bathroom condo with 2 parking spaces and in-unit washer/dryer. This meticulously cared-for unit offers a comfortable living space with added ...
- 2 Beds
- 2 Baths
- 202600205 MLS
- FS - Fee Simple Tenure
- Regency Park Bldg.
- 147 DOM
Welcome home! This beautifully crafted 5-bedroom, 3-bathroom home with 3/2 upstairs and 2/1 downstairs located on the highly desirable 20th Avenue in Kaimuki. Thoughtful...
- 5 Beds
- 3 Baths
- 202525253 MLS
- FS - Fee Simple Tenure
- 51 DOM
Nestled in the heart of Kahala, this four-bedroom, two-bath residence, featuring a separate one-bedroom, one-bath guest suite, sits on an elevated 12,049 sq. ft. lot that...
- 5 Beds
- 3 Baths
- 202519413 MLS
- FS - Fee Simple Tenure
- 270 DOM
Direct oceanfront! Luxuriously upgraded corner apt., with 2 bedms, walk in closet, 2 baths, large media room plus a spacious home office. There are just 2 apts per floor ...
- 2 Beds
- 2 Baths
- 202519492 MLS
- FS - Fee Simple Tenure
- 3003 Kalakaua Bldg.
- 356 DOM
Seize this incredible opportunity to own a multi-unit gem in the heart of Honolulu, boasting jaw dropping Diamond Head and Ocean Views. This versatile property features ...
- 4 Beds
- 4 Baths
- 202516728 MLS
- FS - Fee Simple Tenure
- 198 DOM
Kalani Iki Estates is known for its park-like setting and amenities, including a pool, BBQ area, tennis court, walking paths and more. Nestled amidst its lush greenery, t...
- 4 Beds
- 3 Baths
- 202515263 MLS
- FS - Fee Simple Tenure
- Kalani Iki Estates Bldg.
- 34 DOM
This Waialae Iki 3 bedroom, 2.5 bathroom home with 2 car garage & pool boasts beautiful ocean views. There are 2 extra rooms without closets that might be used as bedroom...
- 3 Beds
- 3 Baths
- 202514216 MLS
- FS - Fee Simple Tenure
- 117 DOM
Welcome to this refreshed home in Waialae Nui Ridge, designed by renowned architect Vladimir Ossipoff. This property features a 3-bedroom, 2-bath main residence plus a de...
- 3 Beds
- 3 Baths
- 202514283 MLS
- FS - Fee Simple Tenure
- 102 DOM
GENEROUSLY PRICED WITH RARE CENTRAL AIR CONDITIONING and RENOVATED. Enjoy this serene stretch of Honolulu’s prestigious Gold Coast offering the Best Island Lifestyle tha...
- 2 Beds
- 2 Baths
- 202513430 MLS
- FS - Fee Simple Tenure
- Oceanside Manor Bldg.
- 71 DOM
Unbeatable Location Near Beaches, Golfing, and More… This spacious 5-bedroom 4-bath residence is located on one of Kahala’s most desirable streets. Rich hardwood floors a...
- 5 Beds
- 4 Baths
- 202512860 MLS
- FS - Fee Simple Tenure
- 127 DOM
This rarely available, recently remodeled corner-lot residence offers privacy, tranquility, & prime access to Oahu’s most sought-after lifestyle amenities. This gated hom...
- 4 Beds
- 5 Baths
- 202512334 MLS
- FS - Fee Simple Tenure
- 170 DOM
Don't miss this opportunity for a well priced, beautiful and large 1-bedroom unit a popular, Diamond Head Apartment's Ltd. A well-managed and maintained building FEATURES...
- 1 Beds
- 1 Baths
- 202510400 MLS
- FS - Fee Simple Tenure
- Diamond Head Apts Ltd Bldg.
- 284 DOM
Welcome to Regency Park, two private residential towers with 24-hr security conveniently located below Chaminade University in the desirable St Louis Heights neighborhood...
- 2 Beds
- 2 Baths
- 202503364 MLS
- FS - Fee Simple Tenure
- Regency Park Bldg.
- 52 DOM
Top floor 2 bed/2 bathroom unit in the famed Kahala Beach apartments! Ideally situated on the top floor with the privacy no one living above you and wonderful amount of n...
- 2 Beds
- 2 Baths
- 202506540 MLS
- LH - Leasehold Tenure
- Kahala Beach Bldg.
- 123 DOM
This charming single-level home, built in 1995, offers 3 bedrooms and 2 bathrooms, providing comfort and convenience and perfectly situated on a beautiful corner lot at 9...
- 3 Beds
- 3 Baths
- 202501969 MLS
- FS - Fee Simple Tenure
- 67 DOM
Stunning direct beachfront trophy estate on Kahala Avenue with a land area of over 33,000 square feet and 125.5 linear feet of sandy beach frontage. The private and gated...
- 5 Beds
- 9 Baths
- 202426768 MLS
- FS - Fee Simple Tenure
- 205 DOM
Welcome to 3852 Poka Street, a distinctive luxury residence where island sophistication blends with traditional Japanese design in the heart of Diamond Head. This one-of-...
- 4 Beds
- 4 Baths
- 202418717 MLS
- FS - Fee Simple Tenure
- 186 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
Welcome to Kahala's Mediterranean masterpiece on Aukai Avenue, a haven for luxury living and entertaining. This custom home boasts a gourmet kitchen with Viking, Sub-Zero...
- 6 Beds
- 7 Baths
- 202323944 MLS
- FS - Fee Simple Tenure
- 44 DOM
Situated on an idyllic tree-lined street on lower Waialae Iki, sits this spacious 4 bedroom, 3 bath home. As you enter the front gate, you are greeted by an open courtyar...
- 4 Beds
- 3 Baths
- 202319496 MLS
- FS - Fee Simple Tenure
- 231 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
NEW LISTING - This RARELY available PENTHOUSE 2Bed/2Bath/2 parking stall unit has been FULLY RENOVATED and features new stainless steel appliances, custom cabinets, quart...
- 2 Beds
- 2 Baths
- 202321231 MLS
- FS - Fee Simple Tenure
- Regency Park Bldg.
- 94 DOM
Easy to show to qualified buyers. Beautiful custom built home built w/ award winning team, Jim Schmit, architect, Kahala Construction, Maura Fujihira, Interior designer. ...
- 4 Beds
- 5 Baths
- 202328511 MLS
- FS - Fee Simple Tenure
- 180 DOM
Don't miss this immaculately renovated 5 bed, 3 bath, single level home where island classic meets modern in the coveted Diamond Head neighborhood. The home includes a 1 ...
- 5 Beds
- 3 Baths
- 202311785 MLS
- FS - Fee Simple Tenure
- 255 DOM
Welcome home to your dreams at 313 Kuliouou Road! This four bedroom, four bathroom home is a gem perfect for multi-generational living or rental potential! Separated int...
- 4 Beds
- 4 Baths
- 202407792 MLS
- FS - Fee Simple Tenure
- 47 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.