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Diamond Head Luxury Vacation Rentals, Beachfront Homes & Villas

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Diamond Head Grandeur
5 Beds
5.5Baths
10Sleeps
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Seaside Hideaway 5BR Estate*
5 Beds
4Baths
10Sleeps
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( 1 )
Diamond Head Surf House
3 Beds
3.5Baths
8Sleeps
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( 32 )
Hale Makai at Diamond Head
3 Beds
3.5Baths
8Sleeps
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( 1 )
Casa de Makalei
4 Beds
4.5Baths
8Sleeps
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( 2 )
Hale Mahie
4 Beds
3.5Baths
8Sleeps
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( 3 )
Hale Nui
4 Beds
3Baths
9Sleeps
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Seaside Hideaway*
3 Beds
2Baths
6Sleeps
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Kaimana Retreat*
3 Beds
2.5Baths
6Sleeps
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Colony Surf Getaway
2 Beds
2Baths
6Sleeps
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Executive Gold Coast Oceanfront Suite
2 Beds
2Baths
4Sleeps
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Diamond Head Bali Retreat**
3 Beds
2Baths
6Sleeps
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( 2 )
Hale Le'ahi
5 Beds
4Baths
10Sleeps
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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.