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Diamond Head Neighborhood Guide

Diamond Head really does have it all. The cozy oceanfront neighborhood has the eponymous Crater and Monument, Diamond Head Beach Park, the thriving commercial strip of Kapahulu Ave., the Ala Wai Golf Course, and the Wa‘ahila Ridge hiking trail. Plus, the ‘hood shares borders with both the uber-upscale residential streets of Kahala and foodie-favorite Waialae Ave. in Kaimuki. Residents enjoy easy access to Kapi‘olani Park (walkable and bikeable from many parts of the neighborhood) and the quieter beaches on the edge of Waikiki.  

Key Details

1. WHAT TO EXPECT
Nearly everything a person might desire can be found here, from ocean to jungle, outdoor sports to boutique gyms, quick plate lunch to five star dining. Expect a lot—you’ll find it!

2. THE LIFESTYLE
Laid back and friendly: peak South Shore style.

3. WHAT NOT TO EXPECT
Deep jungle or full-on urbanity: Diamond Head is, in many ways, the perfect compromise between North Shore and town, with enough buzz to be exciting but not so much as to overwhelm. That said, the beach and the hikes are never empty of other people, and to do serious business (or, for many folks, to commute to the office) you’ll likely have to take a drive downtown. 

4. THE MARKET
Condos and single family homes, with smaller apartment buildings near the ocean, historic palatial mansions tucked away on some of the backroads, and a block of adorable historic oceanfront French Tudors that have barely changed hands since the 1970s. 

5. YOU’LL FALL IN LOVE WITH
The cafes and lunch spots. Between world-renowned Ono Seafood, sophisticated Ars Cafe, and quirky yummy Pioneer Saloon, some of the best casual restos on O‘ahu can be found right in this ‘hood.

Attributes

Hip, Low-key, Pricey, Classic South Shore, Down to Earth, Quiet & Serene, Parks & Recreation, For Foodies, Waterfront Views, Great Outdoor Spaces


Located in Urban Honolulu

Commute Times

Airport: 30m by car
Downtown: 15m by car
Diamond Head: 0m by car
North Shore: 1hr by car
Kapolei: 45m by car

Boundaries

East to West Palolo Ave. and Alohea St. to Manoa Stream and Koali Rd.
North to South Wa‘ahila Ridge State Rec Area to Ocean
Nearby Neighborhoods Kahala, Waikiki, Kaimuki, Manoa


Around the Block

Diamond Head: the jewel of the South Shore

Named Lēʻahi in Hawaiian (which roughly translates to “brow of the tuna”) for its resemblance to the dorsal fin of the ahi, the neighborhood’s eponymous crater was dubbed “Diamond Head” by confused British sailors who, upon arrival in the 1800s, mistook the sparkling calcite crystals for diamonds.

What to Expect

Nearly everything a person might desire can be found here, from ocean to jungle, outdoor sports to boutique gyms, quick plate lunch to five star dining. Expect a lot—you’ll find it!

Close to both Waikiki and downtown Honolulu, Diamond Head is super convenient and feels small despite its many amenities. This is the kind of nabe where most folks have a regular lunch spot and coffee bar, and sprawling Kapi‘olani Park is host to all kinds of leisure and athletic activities.

The Lifestyle

Laid back and friendly: peak South Shore style.

Diamond Head is a little bit younger and hipper than elegant Kahala, but this is definitely still an upscale neighborhood, as evidenced by the historic architecture and genteel street life. 

Residents tend to live quiet, community-oriented lives, patronizing the local restaurants and shops, frequenting the beaches and parks, and steering clear of the tourist-heavy crater hike, which is as crowded as it is beautiful. 

Living the outdoor lifestyle is beyond easy in Diamond Head, where it is possible to walk to the beach from many points for a surf or swim. The Diamond Head Loop is a favorite for runners, with free outdoor gym equipment as well as bathrooms and water fountains along the path. 

Kiddos (and parents) appreciate easy access to calm Kaimana Beach, Waikiki Aquarium, and the wonderful Honolulu Zoo.

Tourists and residents alike line up for the popular healthy-ish sweet treat options on Monsarrat Ave: real-fruit shave ice at Monsarrat Shave Ice, açai bowls at Da Cove Health Bar, and banana “nice cream” at the Banán truck.

What Not to Expect

Deep jungle or full-on urbanity: Diamond Head is, in many ways, the perfect compromise between North Shore and town, with enough buzz to be exciting but not so much as to overwhelm. That said, the beach and the hikes are never empty of other people, and to do serious business (or, for many folks, to commute to the office) you’ll likely have to take a drive downtown.

Because it so perfectly splits the difference between small town vibes and big city feel, Diamond Head is lacking in things like big box stores and late nightlife on the one side, and remote wilderness jungle on the other. For many residents, that is the point, but if solo hiking or fast access to Costco are desired, you’ll want to look elsewhere.

The Market

Condos and single family homes, with smaller apartment buildings near the ocean, historic palatial mansions tucked away on some of the backroads, and a block of adorable historic oceanfront French Tudors that have barely changed hands since the 1970s.

Midpriced condos turn over fairly regularly on sweet cul-de-sacs and roundabouts like Pualei Circle, which is just a block from the “main drag” of Monsarrat Ave but feels private and tucked away.

You'll Fall in Love With

The cafes and lunch spots. Between world-renowned Ono Seafood, sophisticated Ars Cafe, and quirky-yummy Pioneer Saloon, some of the best casual restos on O‘ahu can be found right in this ‘hood. 

Other Neighborhoods to Explore

Ala MoanaAla Moana neighborhood guide
ManoaManoa neighborhood guide
KaimukiKaimuki neighborhood guide

Newest Diamond Head Homes and Condos for sale

2895 Kalakaua Avenue Unit 109, Honolulu image
2895 Kalakaua Avenue Unit 109, Honolulu — Colony Surf Ltd $798,000

Presenting Colony Surf #109, a thoughtfully, elegantly remodeled unit in Diamond Head’s prestigious beachfront condo, Colony Surf. Upgraded in 2014 with hardwood floors, ...

  • 1 Beds
  • 1 Baths
  • 202109302 MLS
  • FS - Fee Simple Tenure
  • Colony Surf Ltd Bldg.
  • 0 DOM
3111 Pualei Circle Unit 204, Honolulu image
3111 Pualei Circle Unit 204, Honolulu — Hale Pua Lei $485,000

The beach lifestyle you're looking for in a move in ready condo. All that stands between you and and hopping in the water is a short stroll across Kapiolani park. The ent...

  • 1 Beds
  • 1 Baths
  • 202109291 MLS
  • FS - Fee Simple Tenure
  • Hale Pua Lei Bldg.
  • 0 DOM
2943 Kalakaua Avenue Unit 105, Honolulu image
2943 Kalakaua Avenue Unit 105, Honolulu — Tropic Seas Inc $435,000

This bright and spacious studio has great island breezes and is just steps from the ocean. Start your day with a cup of coffee on the community oceanfront Hau Terrace. ...

  • 1 Baths
  • 202109045 MLS
  • FS - Fee Simple Tenure
  • Tropic Seas Inc Bldg.
  • 3 DOM
3027 Pualei Circle Unit 110, Honolulu image
3027 Pualei Circle Unit 110, Honolulu — Diamond Head Alii Corp $535,000

A great opportunity to grab your own slice of Pualei Circle! This charming ground floor 1 bed/1 bath unit has a lot to offer with an open layout and fresh indoor-outdoor ...

  • 1 Beds
  • 1 Baths
  • 202108604 MLS
  • FS - Fee Simple Tenure
  • Diamond Head Alii Corp Bldg.
  • 9 DOM
3824 Leahi Avenue Unit 216, Honolulu image
3824 Leahi Avenue Unit 216, Honolulu — Diamond Head Surf $580,000

Rarely available nice 2 bedroom and 1 bath condo. Excellent location, close to the beautiful Sans Souci Beach, Waikiki Beach, Kapiolani Park, and the famous Diamond Head....

  • 2 Beds
  • 1 Baths
  • 202108450 MLS
  • FS - Fee Simple Tenure
  • Diamond Head Surf Bldg.
  • 12 DOM
2801 Coconut Avenue Unit 6H, Honolulu image
2801 Coconut Avenue Unit 6H, Honolulu — Kainalu $799,000

Great opportunity to own in the Coveted Kainalu on the Gold Coast WITH PARKING!. This builidng is oceanfront with it own beach in front. As a corner unit you have city, m...

  • 1 Baths
  • 202108408 MLS
  • FS - Fee Simple Tenure
  • Kainalu Bldg.
  • 11 DOM
2957 Kalakaua Avenue Unit 517, Honolulu image
2957 Kalakaua Avenue Unit 517, Honolulu — Diamond Head Ambassador C $750,000

Life on the Gold Coast! Beautiful ocean, garden and sunset views. Near Waikiki Beach, Outrigger Canoe Club, Kapiolani Park and much more. This unit has been converted to ...

  • 2 Beds
  • 1 Baths
  • 202108282 MLS
  • FS - Fee Simple Tenure
  • Diamond Head Ambassador C Bldg.
  • 13 DOM
2957 Kalakaua Avenue Unit 607, Honolulu image
2957 Kalakaua Avenue Unit 607, Honolulu — Diamond Head Ambassador B $1,388,000

A penthouse so rare, at THIS price it could be yours! Diamond Head Ambassador boasts historic architecture, so perfectly oriented between the blue Pacific Ocean & histori...

  • 3 Beds
  • 2 Baths
  • 202106613 MLS
  • FS - Fee Simple Tenure
  • Diamond Head Ambassador B Bldg.
  • 15 DOM
3111 Pualei Circle Unit 302, Honolulu image
3111 Pualei Circle Unit 302, Honolulu — Hale Pua Lei $620,000

Top floor condo with cool trade winds and a gorgeous view of iconic Diamond Head! Highly desirable Pualei Circle located within minutes to Kapiolani Park, Waikiki Beach a...

  • 2 Beds
  • 1 Baths
  • 202108227 MLS
  • FS - Fee Simple Tenure
  • Hale Pua Lei Bldg.
  • 15 DOM
3824 Leahi Avenue Unit 120, Honolulu image
3824 Leahi Avenue Unit 120, Honolulu — Diamond Head Surf $599,000 ▼

Located at the bottom of world famous Diamond Head this 2 bedroom unit has the feel of a small cottage. Plantation shutters throughout. Close to Kapiolani Park, Waikiki...

  • 2 Beds
  • 1 Baths
  • 202107987 MLS
  • FS - Fee Simple Tenure
  • Diamond Head Surf Bldg.
  • 17 DOM
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