The full-back was previously out on loan with Bournemouth earlier this season, but failed to make an appearance for the Cherries.
The Star reports that the 25-year-old could complete a move to the Owls today, subject to a medical.
With Carlos Carvalhal's side's weekend victory in the Yorkshire derby over Leeds taking the club inside the Championship's play-off places, the Portuguese appears keen to bolster his squad during the January window to ensure that they do not run out of steam later on in the campaign.
The full-back brings plenty of Championship experience - having come through the youth ranks at current leaders Middlesbrough, and having spent last season on loan at Brighton - and perhaps more importantly, a degree of Premier League experience, having made 30 top flight appearances for the Villains.
However, Bennett will certainly have something to prove, should he complete his switch, as he has found opportunities much more difficult to come by this term.
Having made just one appearance for Villa this season - in the Capital One Cup victory against Notts County, during which he also scored - he was allowed to join Bournemouth on loan on the summer window's deadline day (via Star). However, an Achilles injury meant that he did not feature for the Cherries before returning to his parent club.
Having now returned to fitness, he will be keen to prove to Remi Garde that he could have helped the Premier League's bottom club drag themselves out of their desperate situation, by helping the Owls book their place at English football's top table.