Diamond Head Luxury Vacation Rentals, Beachfront Homes & Villas

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Hale Makai at Diamond Head

3 Bed | 3.5 Bath | 8 Sleep | Honolulu

Starting at $1,250.00/night

Diamond Head Grandeur

5 Bed | 5.5 Bath | 10 Sleep | Honolulu

Starting at $934.00/night

Diamond Head Surf House

3 Bed | 3.5 Bath | 8 Sleep | Honolulu

Starting at $671.00/night

Hale Nui

4 Bed | 3 Bath | 9 Sleep | Honolulu

Starting at $417.00/night

Hale Mahie

4 Bed | 3.5 Bath | 8 Sleep | Honolulu

Starting at $400.00/night

Executive Gold Coast Oceanfront Suite

2 Bed | 2 Bath | 4 Sleep | Honolulu

Starting at $250.00/night

Seaside Hideaway 5BR Estate*

5 Bed | 4 Bath | 10 Sleep | Honolulu

Starting at $3,000.00/night

Le Reve at Diamond Head*

3 Bed | 4.5 Bath | 10 Sleep | Honolulu

Starting at $2,500.00/night

Seaside Hideaway*

3 Bed | 2 Bath | 6 Sleep | Honolulu

Starting at $1,750.00/night

Kaimana Retreat*

3 Bed | 2.5 Bath | 6 Sleep | Honolulu

Starting at $1,103.00/night

Hale Le'ahi*

5 Bed | 4 Bath | 10 Sleep | Honolulu

Starting at $750.00/night

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A History of Luxury Living

Diamond Head has the feel of Beverly Hills and Santa Monica combined with the beauty and climate of Hawaii. In one of the most convenient spots on the island, the Diamond Head area brings luxury homes with quick drives to anything imaginable. Just off the beaches of Diamond Head is great south shore surfing and kite surfing for the water lovers. Hop in the car for a trip to the famous Sandy Beach to watch the body surfers, then an afternoon at Makapu’u Beach or head in to Waikiki for dinner or shopping. Take a short scenic drive along the coast to incredible snorkeling at the world-renown Hanauma Bay or hiking Koko Head stairs or into the crater.

Diamond Head Crater is an old volcanic cone crater not far from Waikiki. Now dormant, Diamond Head was named as such in the 1800’s when sailors mistakenly believed there were diamonds located in the crater. Although the sailors were confused, the name stuck. In the early 1900’s a lighthouse was built to help guide vessels into the Honolulu Harbor. The military utilized the crater after purchasing it in 1904, leaving behind bunkers, which are now a popular hiking destination. As the surrounding neighborhood developed, homes began to gather in this convenient and beautiful spot. Notable locals such as Walter Dillingham built large estates in Diamond Head and others flocked to join, establishing this area as one filled with large estates and luxury homes.

This area is one of the most desirable spots on Oahu. Beachfront homes sell for anywhere between $5-50 million and a trip to Diamond Head makes it obvious why. Close to downtown, picturesque beaches, and a myriad of outdoor activities readily available, the addition of beautiful homes makes this an unbeatable spot for those seeking luxury living with everything at their fingertips. With a Whole Foods, dozens of restaurants, and the shops and boutiques of Kahala Mall within striking distance Diamond Head is gorgeous and practical, providing for every need imaginable.