Diamond Head Homes with Leasehold Land tenure

Welcome to Diamond Head, a stunning neighborhood nestled on the southeastern coast of Oahu, Hawaii. Renowned for its iconic volcanic crater and breathtaking ocean views, Diamond Head is a paradise that perfectly blends natural beauty with vibrant local culture. This charming community is just a short drive from the bustling streets of Honolulu, offering residents the best of both worlds—tranquility and convenience.

The homes in Diamond Head are as diverse as the landscape itself, featuring a mix of architectural styles that range from cozy beach cottages to luxurious oceanfront estates. A unique aspect of this neighborhood is the prevalence of leasehold land tenure, which provides an attractive opportunity for those looking to invest in this highly sought-after area. Leasehold properties can offer a more affordable entry point into the Diamond Head real estate market, allowing you to enjoy the beauty of island living without the hefty price tag of freehold properties.

Residents of Diamond Head benefit from a plethora of outdoor activities, including hiking the famous Diamond Head State Monument, surfing the pristine waves of nearby beaches, and enjoying leisurely strolls along scenic coastal paths. The area's rich cultural heritage is reflected in its local eateries, boutique shops, and community events, making it a lively place to call home.

Whether you're seeking a serene retreat or an active lifestyle, Diamond Head offers an unparalleled living experience. Embrace the island life and discover the charm of this exquisite neighborhood where every day feels like a vacation.

Newest Diamond Head Homes with Leasehold Land tenure

$900,000

2 Beds ⋅ 2 Baths ⋅ 202600206 MLS ⋅ LH - Leasehold Tenure ⋅ 152 DOM ⋅ Sans Souci Inc BLDG.

Experience classic Gold Coast living at Sans Souci. This wonderfully maintained high-floor residence enjoys a view plane that clears the Kaimana Beach Hotel, opening to ocean, palms, and cool tradewinds. The flexible layout lives like a spacious 1-bedroom, with an additional area perfect for guests, office, or a sleeping alcove. A smart opportunity for those who appreciate value - Why tie up millions of dollars in paying for a Fee Simple $3,000,000+ condo when you can buy this $900,000 Leasehold condo that offers a much more affordable way to enjoy the same lifestyle - even with lease rent and maintenance fees (inclusive of taxes, insurance and utilities). Ask us for the breakdown! Plus, the potential to generate income that helps offset monthly fees while still enjoying this unmatched lifestyle location. Currently rented with a 30-day minimum stay requirement. Beloved oceanfront building steps to Kaimana Beach, Outrigger, Kapiolani Park, and Waikiki dining. A special offering combining location flexibility, and oceanfront living.

2877 Kalakaua Avenue Unit 1107, Honolulu

$175,000

1 Baths ⋅ 202518765 MLS ⋅ LH - Leasehold Tenure ⋅ 329 DOM ⋅ Diamond Head Bch Hotel BLDG.

OCEAN FRONT ~ GOLD COAST Diamond Head Beach Hotel & Residence is the only building on the Gold Coast that offers legal vacation rentals. Great rental income potential and enjoy the condo amenities at your leisure. Currently owner-managed on vacation rental platforms with the option to use the on-site Hotel Management with front desk operations. Enjoy the beautiful ocean front tropical landscaped grassy lawn. Direct access to the ocean for swimming and sporting. Sans Souci is near-by for beach activities with life-guard. Kapiolani park offers community tennis/pickle ball courts and events. Elk's and Outrigger Canoe Club are next-door along with the Waikiki Aquarium and fine dining. Diamond Head is close enough to enjoy all of Waikiki yet is more of a serene neighborhood embraced with the spirit of Aloha. Plenty of street parking free/metered is available and also gated garage parking (fee). Security guard on-site nightly, FOB gated access, security cameras and fire sprinklers. Showings by appointment subject to bookings. This is a Lease-Hold property, contact Listing Agent for more information. ~Mahalo

2947 Kalakaua Avenue Unit 302, Honolulu

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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.