Richard Branson — Necker Island ($5,000/Night)

Branson bought a 74-acre private island in the British Virgin Islands for $180,000 in 1978 when he was 28 — the deal of the century. Necker Island now rents for $5,000 per person per night (with a 34-guest minimum for exclusive hire: $170,000 per night for the whole island). It comes with flamingos, lemurs, a infinity pool overlooking the Caribbean, and Branson himself occasionally showing up in a bathrobe. The island burned down twice (2011 and 2013) and was rebuilt both times.