Looks like Chief Keef really loves Florida. If he were to shack up at the W Hotel in South Beach, he can wine and dine at Mr. Chow and The Dutch, and while he's not yet legal to hit up the six destination bars, you never know what Keef is capable of. A month at the W Hotel in South Beach in a penthouse suit with a full panoramic view, an outdoor plunge pool, and a full kitchen would definitely blow through some cash.

Estimated Cost: $8,200 per night (Penthouse suite)