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.
Most Popular
-
1
Portsmouth loan strategy revealed following duo's arrival from Ipswich and Blackpool respectively
-
2
Predicted Portsmouth XI v Cheltenham: changes expected to side that beat Cardiff so handsomely - but attacking duo could keep places and defender set to return
-
3
Portsmouth boss Danny Cowley spells out why Blues can rival Sheffield Wednesday, Ipswich and Derby for promotion as he prepares for welcome return to Cheltenham
-
4
Portsmouth boss Danny Cowley hails Spurs loanee Dane Scarlett as move already shows signs of putting Miguel Azeez's short stint from Arsenal in shade
-
5
‘For the sake of 90 minutes football, it’s not worth a player being off work for a year or ending up in a wheelchair’ – Hampshire grassroots football clubs postpone matches due to the heatwave
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.
Blues winger Reeco Hackett-Fairchild is currently on loan at Roots Hall and has scored once in six appearances.
Ex-Fratton favourite Greg Halford is also presently representing the Shrimpers.