Diamond Head Homes under $300,000

Welcome to Diamond Head, a picturesque gem nestled in the heart of Honolulu, Oahu. Known for its iconic volcanic crater and breathtaking ocean views, this vibrant neighborhood offers a unique blend of natural beauty and urban convenience. With its stunning beaches, lush landscapes, and rich cultural heritage, Diamond Head is a sought-after destination for both residents and visitors alike.

In this enchanting region, you’ll find a variety of homes available, including some hidden treasures priced under $300,000. These affordable options provide an excellent opportunity for first-time homebuyers, investors, or those looking to downsize without compromising on the vibrant lifestyle that Diamond Head offers. Imagine waking up to the sound of crashing waves and the scent of salt in the air, all while living in a charming abode that fits your budget.

Residents of Diamond Head enjoy access to a plethora of outdoor activities, from hiking the famous Diamond Head State Monument to relaxing on the nearby sandy beaches. The neighborhood is also known for its rich history, with cultural landmarks and local eateries that showcase the unique flavors of Hawaiian cuisine.

Living in Diamond Head means embracing a lifestyle filled with adventure, relaxation, and community. Whether you’re sipping a morning coffee with a view of the Pacific or exploring the nearby shops and markets, this area is sure to capture your heart. Discover the possibilities of calling Diamond Head home, where affordability meets paradise!

Newest Diamond Head Homes under $300,000

$270,000

1 Beds ⋅ 1 Baths ⋅ 202618394 MLS ⋅ FS - Fee Simple Tenure ⋅ Kaimuki Jade BLDG.

This charming, nicely decorated Kaimuki 1-bedroom offers a rare mix of location, parking, and smart interior upgrades at an accessible price point. The competitive list price and low current monthly maintenance fee create an exceptional value that is hard to find in Honolulu. The 453 sq. ft. layout is efficient and comfortable, with a remodeled bathroom, custom Inspired Closets wall unit for added storage and style, and a private storage locker for extra convenience. Located in a secure-entry building with two recently installed elevators and laundry available on every floor. One unassigned parking stall is included. Set in the vibrant, walkable heart of Kaimuki, the property is near local eateries, shops, pubs, banks, bus lines, and quick access to H-1, Waikiki, the University of Hawaii, and Chaminade. A strong option for a first-time buyer, investor, or anyone looking for value, convenience, and lower monthly ownership costs. Unit is being sold As Is. Special assessment has been paid off.

1139 9th Avenue Unit 202, Honolulu

Listing courtesy of OahuRE.com.

$95,000

2 Beds ⋅ 2 Baths ⋅ 202616172 MLS ⋅ LH - Leasehold Tenure ⋅ Kahala Beach BLDG.

Enjoy coastal chic living in this well-appointed and cared for Kahala Beach residence located one back from the ocean. A rare offering in the preferred building (three stack), enjoy beautiful views of the Pacific Ocean from your lanai. Updated in 2021 with refreshed carpet, tasteful decor and well thought out upgrades that show pride of ownership. Two parking stalls included, both located in your building'sgarage. Property is Leasehold and no fee purchase option is available. Please consult with your Realtor to ensure You are fully aware of what Leasehold ownership entails at Kahala Beach Apartments. Monthly fees (estimated, please confirm) are: $2,565/month in Lease Rent, $1,371.31/month in Maintenance Fees and $863.43/mo nth in Property Taxes. Leasehold expires on July 15th 2027, no lease renewal or extension will occur. Owners will have the option to sign a rental lease agreement with Lessor after the leasehold expires, but with an initial contract date no longer than July 31st, 2028.

4999 Kahala Avenue Unit 250, Honolulu

Listing courtesy of Portfolio.

$24,000

2 Beds ⋅ 2 Baths ⋅ 202615328 MLS ⋅ LH - Leasehold Tenure ⋅ Kahala Beach BLDG.

Experience island living in this beautifully upgraded 2 bdrm/2 bath residence in the desirable Kahala Beach oceanfront community. Tastefully renovated with modern finishes throughout, the unit features vinyl plank flooring, an updated kitchen with stainless steel appliances, and refreshed bathrooms. The spacious enclosed, covered lanai provides a comfortable extension of the living space—perfect for relaxing or enjoying the lush surroundings. The generously sized primary bedroom offers a peaceful retreat, while the unit’s private setting is enhanced by abundant greenery. A wonderful opportunity to enjoy the tranquility of Kahala Beach with the convenience of being just minutes from Kahala Mall with options of restaurants, shopping and entertainment! Don’t miss this fantastic opportunity!

4999 Kahala Avenue Unit 202, Honolulu

Listing courtesy of REMAX Hawaii.

$50,000

2 Beds ⋅ 2 Baths ⋅ 202615775 MLS ⋅ LH - Leasehold Tenure ⋅ 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

Listing courtesy of JC Hawaii Realty Corp.

$150,000

2 Beds ⋅ 2 Baths ⋅ 202614285 MLS ⋅ LH - Leasehold Tenure ⋅ 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

Listing courtesy of REMAX Hawaii.

$80,000

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

Leasehold property with a rental opportunity after 2027 lease expiration! Leesees will be offered a rental lease agreement with Lessor after the leasehold expires July 2027 with an initial contract end date of July 31, 2028. 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

Listing courtesy of Five Star Realty, Inc..

$275,000

3 Beds ⋅ 2 Baths ⋅ 202601168 MLS ⋅ LH - Leasehold Tenure ⋅ 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. Lease expires July 15, 2027.

4999 Kahala Avenue Unit 101, Honolulu

Listing courtesy of Coldwell Banker Realty.

$175,000

1 Baths ⋅ 202518765 MLS ⋅ LH - Leasehold Tenure ⋅ 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

Listing courtesy of Hawaii Americana Realty.

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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.