Hawaii’s most famous local? President Obama, of course. The President spent his annual winter vacations with his family at Paradise Point Estates in Kailua Bay Beach, the same beach he would visit as a child growing up in Oahu. A world away from Washington, DC, the 44th president and his family unwind in the secluded, heated, lagoon-style pool, complete with lava rocks and waterfalls. 

The First Family’s luxury beachfront rental features a gourmet kitchen, fitness center, oceanfront lanais and secure lava-wall-fenced grounds. 

While filming Aloha, Emma Stone rented this multi-million dollar villa on the base of Diamond Head that starts at $4000 a night. Natural stone and wood details are featured in this high-tech home that is fully controlled by wall-mounted iPads. And perfect for the Hollywood set, the Oahu villa includes a private movie theater. 

Thanks to this home's emphasis on indoor-outdoor living, VIP vacationers spend their days and nights watching the waves break or the sun set in the heated pool or lounging in the poolside cabana, complete with large flat screen TV.