Two books that might be of interest:
My Ancestor Settled in the British West Indies, by John Titford. Published by the Society of Genealogists 2011.
Tracing your West Indian Ancestors, by Guy Grannum
This web site has lots of info on Jamaica families:
http://jamaicanfamilysearch.com/ There is a zip file to download to see if your surname(s) appear. If so, a one month subscription is just $9 (USD).
Regards,
Paul
Tittensor One-Name Study homepage:
www.tittensor.com