[Posted by WLS]
The house is legal as a vacation rental, but only on a monthly basis. The community where the house is located — Kailua — has had an ongoing internal battle for years over owners of second homes using them as “short-term” rentals — generally meaning houses that are rented on a daily or weekly basis. Short-term rentals — like Bed&Breakfasts — are not allowed, unless specifically licensed.
The house Obama rented is not licensed as a “short-term” rental, which means the owner can rent it only one time a month. I don’t know for sure what Obama paid, but I know someone who rented a smaller house on the same beach on a monthly basis in the same basic area, and the monthly rental was $18,000. The house Obama rented is much bigger and newer.