Trvellover, I guess it depends on what he wants to do on his vacation. If he wants to hole up in an all inclusive resort then I would suggest staying in Montego Bay. If he wants to get out and see the countryside then I would suggest the north coast. If he wants to party all day and night then maybe Negril.
BTW, do you know if the hotel in this thread is any good?
water-hotel-negril-t1590.html