Diamond Head Homes with Leasehold Land tenure

Welcome to Diamond Head, one of Honolulu’s most iconic neighborhoods, where breathtaking natural beauty meets vibrant island living. Nestled on the southeastern coast of Oahu, Diamond Head is renowned for its stunning volcanic crater, which offers panoramic views of the Pacific Ocean and the lush landscapes of Hawaii. This picturesque region is not just a feast for the eyes; it’s also a haven for outdoor enthusiasts, with ample opportunities for hiking, surfing, and enjoying the sun-kissed beaches.

Living in Diamond Head means immersing yourself in a community that celebrates both its rich cultural heritage and modern conveniences. The area is dotted with charming local shops, delightful eateries, and vibrant markets, ensuring that residents have access to everything they need right at their fingertips. The proximity to Honolulu adds to the allure, providing easy access to the bustling city life while still allowing for a tranquil retreat at home.

One unique aspect of Diamond Head real estate is the prevalence of homes with leasehold land tenure. This means that while you can enjoy the benefits of homeownership, the land itself is leased, often making properties more affordable than their fee-simple counterparts. This arrangement is particularly appealing for those looking to invest in a slice of paradise without breaking the bank.

Whether you’re seeking a cozy beach bungalow or a luxurious oceanfront condo, Diamond Head offers a diverse range of properties to suit various lifestyles. Experience the magic of living in this enchanting neighborhood and embrace the vibrant spirit of Hawaii. Your dream home awaits in Diamond Head!

Newest Diamond Head Homes with Leasehold Land tenure

$50,000

2 Beds ⋅ 2 Baths ⋅ 202615775 MLS ⋅ LH - Leasehold Tenure ⋅ 3 DOM ⋅ Kahala Beach BLDG.

Enjoy the beauty and serenity of Kahala Beach from this spacious 1,555 sq ft, 2-bedroom, 2-bathroom ground-floor condominium at Kahala Beach Apartments. Ideally located on Kahala Avenue, this fully furnished residence is just steps from the beach and conveniently close to Kahala Hotel, Kahala Mall, restaurants, shopping, and easy access to Honolulu. The generous floor plan features an enclosed lanai that expands the living space and offers a peaceful garden setting. The unit is fully furnished with comfortable Hawaiian-style décor and includes a king bed in the primary bedroom, two queen beds in the second bedroom, and two sofa beds, providing ample space for family and guests. Enjoy the convenience of ground-floor living with easy access to the pool and recreation areas, plus the ability to bypass the elevator. The property also includes one covered garage parking stall and storage. A unique opportunity to own in one of Honolulu’s desirable beachfront communities. The lease term ends July 2027, but you can rent from Kamehameha schools after providing additional time to enjoy or utilize the property. Maintenance fee includes all utilities. Lease rent paid til October 2026!

4999 Kahala Avenue Unit 148, Honolulu

$150,000

2 Beds ⋅ 2 Baths ⋅ 202614285 MLS ⋅ LH - Leasehold Tenure ⋅ 24 DOM ⋅ Kahala Beach BLDG.

This spacious, garden-view gem in prestigious Kahala is beautifully renovated and move-in ready! Featuring 2 bedrooms, 2 baths, 1 covered parking stall, an open floor plan, and an enclosed lanai, this home is just steps from a sandy beach, Kahala Mall, and the iconic Kahala Hotel. Enjoy direct beach access with a protective offshore reef, offering calm waters for swimming, snorkeling, diving, and paddleboarding. Experience the best of island living. Lease expires July 15, 2027.

4999 Kahala Avenue Unit 422, Honolulu

$495,000

3 Beds ⋅ 3 Baths ⋅ 202614329 MLS ⋅ LH - Leasehold Tenure ⋅ 24 DOM ⋅ Kahala Beach BLDG.

Experience luxury BEACHFRONT living in prestigious KAHALA! This stunning 3b/3b residence offers direct beach access w/a protective offshore reef, creating calm waters ideal for swimming, snorkeling, diving & paddleboarding. Enjoy unobstructed OCEAN & KOKO HEAD views from the spacious enclosed lanai. Highlights incl: HARDWOOD floors, soaring ceilings, custom cabinetry, central A/C, Sub-Zero & Bosch appliances, wine refrigerator, built-in bookshelves & speakers, Toto toilets, dual water heaters & Water Guard sensors. Rare opportunity to own this beachfront paradise! Lease expires July 15, 2027.

4999 Kahala Avenue Unit 472, Honolulu

$80,000

2 Beds ⋅ 2 Baths ⋅ 202607653 MLS ⋅ LH - Leasehold Tenure ⋅ 112 DOM ⋅ Kahala Beach BLDG.

Lease rent paid through September 2026! Perched on the 2nd floor with stunning views of Kahala Beach and the Pacific Ocean, this move-in-ready corner-end condo has been thoughtfully maintained and features upgrades such as updated kitchen and bathrooms, vinyl plank flooring, stainless steel appliances, quartz counters, upgraded cabinets, tiled lanai, plantation shutters and central AC. The covered lanai, framed by floor-to-ceiling glass doors, invite in gentle trade winds and sweeping views of the beach and ocean—an ideal setting for outdoor dining under the stars and moonlight. Bright and inviting, the unit reflects true pride of ownership. This is a leasehold property with a lease expiration date of July 15, 2027, and no option to purchase the fee. Property currently unfurnished; photos taken when previously occupied.

4999 Kahala Avenue Unit 252, Honolulu

$275,000

3 Beds ⋅ 2 Baths ⋅ 202601168 MLS ⋅ LH - Leasehold Tenure ⋅ 211 DOM ⋅ Kahala Beach BLDG.

Kahala luxury living in this highly upgraded, single-level ground floor residence with over 2,000sf. This renovated 3 bedroom, 2 bath home is located in sought after oceanfront Kahala Beach condominium just steps from The Kahala Hotel & Resort and Waialae Country Club. Spacious interiors and mountain views. Features include hardwood flooring, a large galley kitchen with granite countertops and custom cabinetry, and elegant baths with backlit onyx countertops, travertine flooring, Toto toilets and premium fixtures. Wine enthusiasts will love the 6 integrated wine vaults with 400-500 bottle capacity. Additional highlights include custom built-in Chinese elm panels for storage, custom window coverings, and Baldwin hardware, reflecting thoughtful design and exceptional craftsmanship. A beautiful sandy beach fronts the building; amenities include a heated pool, exercise room and security. This is a leasehold property. Your opportunity for an unparalleled lifestyle!

4999 Kahala Avenue Unit 101, Honolulu

$175,000

1 Baths ⋅ 202518765 MLS ⋅ LH - Leasehold Tenure ⋅ 353 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

$300,000

202505404 MLS ⋅ LH - Leasehold Tenure ⋅ 545 DOM

Well-established and beloved authentic Japanese restaurant, proudly serving the community since 2000. Situated in the heart of the popular Kaimuki neighborhood, this local favorite has built a strong reputation, attracting a dedicated base of loyal customers. Turn-key, ready for seamless ownership transition. Sale is subject to landlord approval. Lease is NNN, with the listed rent reflecting base rent only.

3565 Waialae Avenue Unit 108, 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.