John Lennon – Dorinish Island, $42.50K
John Lennon has the most affordable island on this list. He bought Dorinish Island off the coast of Ireland for a poultry $2,100 and while he and his wife, Yoko Ono, had plans to build a cottage on the island, they never did. Ono eventually sold the island for $42 500, giving all proceeds to charity.
It was, however, put to use when, in 1970, Lennon loaned the island to “the king of hippies,” Sid Rawle, who, along with 25 others, lived on the island for two years. Despite being sold, it is still known as Beatle Island and currently operates as a grazing site for livestock.