I've been looking for places to rent planes in the Caribbean, and haven't been able to find anything that wasn't charter service. Does anyone know of any pilot resources or specific rental or flight schools in the Caribbean, specifically the southern Caribbean?
You would be much better off renting the plane in the United States. It will be difficult to find a rental anywhere in the Caribbean, except maybe Puerto Rico.
You may want to read Greenspun's Flying in the Caribbean. It's a little dated but has good information.