There's strong evidence to believe that the Taino societies and the Mesoamericans (Maya especially) had some degree of cultural and goods exchange during pre-Columbian times. With a undetermined POD, preferably around the Classic Maya Collapse in the 8th to 9th centuries, is it possible for wayward Maya to uproot from the Yucatan and establish colonies in the Caribbean islands to escape the political, economic and societal chaos that engulfed the area at the time? Many Classic Maya cities were abandoned and there was an OTL migration of people from the south to the north - I don't think it would be impossible there would be further migration to Isla Juventud and/or western Cuba.
What would be the effect of major Maya enroachment onto traditional (Ciboney) Taino and pre-Taino peoples, like the relatively primitive hunter-gatherer Guanahatabey? I'd figure that in the case of the latter, they would be extinguished or quickly absorbed into the new Maya colonies. The Ciboney would likely prove to be more serious adversaries but in the long term, I see them being expelled/killed off/absorbed except for perhaps for the mountains in the eastern end and swamps. Perhaps they might even adapt and evolve into an equivalent of Rome to the Maya's Greeks? Or likely be conquered by the wave of organized Taino coming from Puerto Rico and Hispaniola?