Wow - that is a big topic. That is like asking where in North
America to go. If I were you, I would start by going to a travel agent and getting some brochures. Study them, and see what appeals most to you. All inclusives with your air fare is usually the best deal, but leaving from Florida there could be other options.
The further south in the Caribbean you go, the hotter it will be.
A couple of my friends have been to Aruba and found it far too hot and humid. Barbados is very popular - also very expensive. Dominican Republic has lots of tourist destinations and is probably one of the most reasonable - Jamaica is also popular. We like Cuba, but being Canadian we can travel there easily.
A travel agent could offer some good last minute deals if your timing is right.
Good luck finding something to your liking and budget.