Kailua. The guidebooks say it’s basically a beach. But there’s a town wrapped around the beach, and, around that, a whole other side of the 600-square-mile island of Oahu — the windward. and the president’s vacation gym. Even at. Hawaiian Islands Bed & Breakfast offers properties in the quaint beach town of Kailua, Oahu. Enjoy your stay even more with Lanikai Beach Rentals! Dec 19, 2013. On Friday, the presidential…