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The Windward side is simple and carefree, where children play on the beach, dogs frolic in the water, and an occasional rooster roams the street. Kailua is a charming town with darling shops and eateries, and it is blessed with a beautiful white sand beach. Kailuaís hip, cool scene appeals to the youngsters, as well as the retirees. The neighborhood is very relaxed and welcoming.