You could try St. barts, SVG air, air mistique, Fly Montserrat, Anguilla Air to fly islanders (BN2), and Island Birds, Fly BVI, VI airline (All in the BVI; Note: FAA license and medical required for Island Birds and Fly BVI) and Cape Air for C402 (US license and or Green card required).
Scheduled and charter Carriers, expect from $2500-4000 a month. most are subjected to regulated days off and will take advantage as much, 10-14 hour duty per day for 6 days a week during high season (October-May)