Lanai Island (Hawaii):
If you’ve ever been to Hawaii, you probably spent a portion of your trip seriously considering moving there. And for $500 million dollars, Larry Ellison demonstrated that you can buy more than just the property your house is on. Though he only owns 98% of the island, and shares it with the 3,000 native inhabitants already living there, Lanai is about as exclusive as Hawaii gets (as it is one of the least populated and developed islands in the chain).