Diamond Head


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Overall average rating.


This neighborhood is very safe.


There are a few good restaurants.


This neighborhood is expensive for amenities.

Remote work

This neighborhood has a few places to work outside the house.

The iconic mountain of Diamond Head takes center stage for the surrounding neighborhoods of Diamond Head and Kahala, one of the state’s most expensive zip codes. With wide, tree-lined avenues and one impressive mansion after the next, Kahala is a quiet, upscale residential neighborhood close to the ocean, while the shopping and dining area of Diamond Head is concentrated on Monsarrat Avenue. Though it is certainly far from affordable, you can still enjoy this area for its many activities and stunning views even if you don’t live here. 

The east-side town of Kailua’s favorite coworking space, Treehouse, just opened an outpost in Kahala, a much-need resource in a district with few remote working locations. The company focuses on networking, community, and sustainability for its entrepreneur and innovator members. Ars Café is a popular hangout on Monserrat Ave, both for those walking around Diamond Head needing a quick cup of Joe and those wanting a quiet place to work. 

Monsarrat Avenue has a couple of establishments for shopping: Pualani Hawaii Beachwear for bikinis and one-pieces, and Kealopiko sells breezy resort wear with native Hawaiian prints located in a sunny yellow cottage. Otherwise, Kahala Mall is the main shopping hub in the area. Check out Mahina for classic and trendy womenswear pieces, and island favorite T&C Surf for all your beach and surf needs. 

Surfers head to Da Cove Health Bar for smoothies and healthy bites before hitting the waves, and later to Pioneer Saloon for poke bowls and delicious seafood “plate lunch.” Diamond Head Market is a neighborhood favorite for to-go meals and tasty pastries. At the exclusive Kahala Hotel, Hoku’s is upscale, oceanfront dining at its best. Over in Kahala, the Olive Tree Café is a popular spot for Greek food, while nearby Et Al, located in Foodland Market, is a cozy, chic restaurant serving seasonal dishes inspired by Hawaii’s diverse cultures. 

The scenery around Diamond Head is some of the best on the island. Take in the views of Kahala the surf from the lookouts on Diamond Head Road, or, if you’re feeling more adventurous, you can do an early morning hike to Diamond Head Crater. Just make sure to leave early, before the midday sun Diamond Head Beach and Kahala Beach are both stunning and perfect for long walks at low tide. Saturday mornings head to the Kapiolani Community College Farmer’s Market for local fruits and veggies and pop-ups from some of the island’s best eateries. For those interested in art and design, make reservations far in advance to see Shangri La, heiress Doris Duke’s impressive estate and ode to Islamic art perched on a cliff above the water.

IJfke Ridgley
November 8, 2022
min read

A half-Dutch writer and photographer who grew up on Oahu, Hawaii. She has spent years exploring and enjoying the Hawaiian Islands for travel and lifestyle publications and assignments.

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