If it were me, I would either fly Orlando to Ft. Lauderdale as cheaply as I could, and then Jet Blue from FLL to SXM. Or, Orlando to Atlanta, and then Delta directly to St. Maarten. Atlanta is roughly 125 miles or so further from The Villages, so it might take a bit longer but not by that much. Jet Blue (FLL) and Delta (ATL) are both airlines I have used in the past and both have served me well when flying to the Caribbean. Why don't you try Kayak or Skyscanner online and see what pops up?
