The 31-year-old became a cult hero at Upton Park during the 2009/10 season, with his technical ability and fiery nature winning him fans in east London.
He eventually left the Irons to head back to Italy, but he’s now currently owned by Chinese giants Guangzhou Evergrande – who have loaned him to Fiorentina.
He may opt to leave the Asian side permanently in the summer, and Sherwood is keen to offer him a route back to England.
The ex-Spurs boss is looking to add more creativity to his Villa side, who are currently the Premier League’s lowest scorers with just 20 goals in 31 games.
Diamanti has been an Italy international in recent years and scored a penalty as the Azzurri knocked England out of EURO 2012.