Besides starring in classic Hollywood films such as Doctor Zhivago and Lawrence of Arabia, actor and playboy Omar Shariff is known for doing really dashing, yet irresponsible things. With a perfect set of eyebrows and tucked cravat, dude clearly thinks he can do whatever he wants. It didn't always work out, though. In fact, in the '70s, he lost his beautiful island retreat in a game of high stakes cards against a British realtor, San Benady. Shariff bought the decadent party pad during a 1973 press tour for Mysterious Islands, and then promptly lost it only a few days after he got it. It was a really bad loss, too: burrowed into a volcanic quarry on the Spanish island of Lanzarote, the house also offers an intricate labyrinth of tunnels, caves, and, you know, volcanic vineyard. Now Casa Omar Sheriff, named as such despite the fact that he owned it for less than a week, can be rented out for £440 a week.
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