Originally Posted by
Pausanias
August and September are the worst possible months for the Caribbean as it's right in the middle of the hurricane season and it's usually wet and windy even if a hurricane doesn't happen. It might be cheaper then, and that's why. Many resorts close.
Agreed. I have friends who have spent most of a week in Punta Cana in their rooms or inside the resort because of the weather.
As alternatives the OP may want to look at Aruba (well south of the usual hurricane tracks) or the pacific coast of Mexico (Los Cabos, Puerto Vallarta, etc).