Larry Ellison – Lanai, $300 Million
Larry Ellison has a net worth in the billions thanks to the Oracle Corporation, his wildly successful company. In 2012, he paid $300 million to buy this Hawaiian island. There are two Four Seasons resorts over there that will give you the experience of a lifetime! If you want to stay at the main penthouse, you need to shell out $21,000 a month. This makes it the priciest resort in all of Hawaii. In 2019, this entrepreneur was reported to have a net worth of $69.1 billion. Aside from co-founding the Oracle Corporation, he is also serving as an executive chairman at the company.