KAILUA O 286 Hawaii Military Guide • Summer-Fall 2026 n the Windward side of Oahu lies the relaxed, close-knit community of Kailua. Surrounded by the breathtaking Koolau Mountain Range and glistening Pacific Ocean with silky soft sandy beaches, this Windward Oahu town is known for its natural beauty and outdoor activities. Kailua also boasts a variety of shops, schools, medical facilities and restaurants, including Target and Whole Foods. Also enjoy farmers’ markets and community events including the annual “I Love Kailua” town party. Many of Kailua’s nearly 40,000 residents live, work and play in “at home”. However, the scenic commute to “town” (Honolulu) along the Pali Highway is only 12 miles away. Kailua borders Marine Corps Base Hawaii, making it a favorite relocation spot for military families. Celebrities can also be spotted on Kailua’s award-winning beaches and residing in the local neighborhoods. Windward Oahu
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