The Most Expensive Resort: An Entire Hawaiian Island | Larry Ellison | $500 million

Larry Ellison made a huge investment and bought Dole Food billionaire David Murdock’s former sparsely inhabited Hawaiian island of Lanai for a whopping $500 million in 2012. This deal made him own 98 percent of this island. Ellison loves to go sightseeing by plane and his island offers this service. The island Lanai boasted 88,000 acres of land with 140-square-mile island, which also held one of the world’s most luxurious hotels, the Four Seasons Lana.

The acquisition reportedly included two Four Seasons retreats, where Ellison planned to build a 100-percent green community. One of the said two resorts were often frequented by several rich and famous personalities, like Jessica Alba, Will Smith, and Cindy Crawford, among others. Bill and Melinda Gates also got married there, on the resort’s Cliffside golf course, next to the 12th hole. The resort was used to be known as Manele Bay Hotel until Ellison had it renovated for eight months, costing him another multi-million dollar.