The 33-year-old has been without a club following the expiry of his short-term contract at Northampton in January.
But the 2014 News/Sports Mail Pompey Player of the Year could be set for a new chapter in his career by linking up with the League Two strugglers.
Southend are in need of some of inspiration as the battle for survival. They currently sit second-bottom after a surprise 1-0 win at Newport on Tuesday night.
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Holmes could be someone manager Mark Molesley turns to in order to keep his side’s Football League status.
That’s despite the former Blues favourite announcing his intention to retire with a back injury last summer – a problem which plagued his time at Sheffield United.
Holmes made 62 appearances for Pompey between June 2013 and December 2014, scoring three goals.
If he links up with hometown club Southend on a permanent basis, they will represent his ninth team during a career spanning 14 years.
He's also represented the likes of Charlton, Oxford United, Barnet and Gillingham after being plucked from non-league.
Should Holmes win a deal at Roots Hall, he will become the third player with Pompey links to sign this season.
Ex-Fratton favourite Greg Halford is also presently representing the Shrimpers.