The Reggae Boyz took the lead twice but were pegged back both times by a determined Trinidad and Tobago side.
A late winner by Richard King in the closing minutes sealed the result for Jamaica and sparked celebrations among their fans on Tuesday night at the Gtech Community Stadium in London.
The match was fast-paced and physical, reflecting the long-standing rivalry between the two Caribbean giants.
Jamaica now advance to the final, where they will face the winner of the second semi-final.
