The Caraways are the GTA IV era equivilent of The Hamptons. They are mentioned in both Grand Theft Auto IV and its expansion packs The Lost and Damned and The Ballad of Gay Tony. The first time is in GTA IV in a blog by Alex Chilton, the second time is during the Mission Clean and Serene in The Lost and Damned whereby Billy chastises Johnny by saying "If you're in The Lost for the good times only and the fairweather weekends in the Caraways then you aint in The Lost, Ya get me". They are also mentioned in the CNT show I'm Rich in a segment about Cloe Parker. It is also mentioned in The Ballad of Gay Tony that Tony Prince has summer parties in The Caraways.
It is possible that the name is a reference to Nick Caraway, a principle character and narrator in the novel The Great Gatsby, set on Long Island.