Our preferred dates are in May but we've done September and October and early November. We managed to catch a hurricane that passed about 75 miles to the south in September, our October (our first time) seemed to be the rainiest time and a little hotter and muggy. December was great except we did have to deal with some northern swell. Except for May all of these are an N of 1 - so YMMV - but if we can we'll take the spring months for fewer crowds, better rates and the best chance of great weather. But we'll take it anytime we can get it.