The 27-year-old Italian international will be available on a Bosman free transfer, and is poised to move to the Premier League.
Gunners boss Arsene Wenger sent assistant Boro Primorac to take in Fiorentina's 2-2 draw with Genoa in Serie A last Sunday - a game in which Montolivo scored and impressed throughout for La Viola.
The Frenchman made enquiries about Montolivo last year, but a move to the Emirates Stadium failed to materialise. As the club look to make a number of key signings at the end of the season, Arsenal could renew their interest in one of their long-term targets.
Montolivo - who was appointed Fiorentina captain midway through the 2009-10 campaign - is best described as a "regista", or a deep-lying playmaker. Though he prefers to operate in the middle, he can in fact play anywhere across the midfield.
His versatility is a valuable attribute that could prove decisive in Wenger's decision to step up his bid to bring him to north London this summer.
Do YOU want to write for GiveMeSport? Get started today by signing-up and submitting an article HERE: http://gms.to/writeforgms