The former Pompey winger is currently out of contract at Southend but is just waiting on chairman Ron Martin to give him the nod on new terms.
Holmes, 34, is continuing to train with the Shrimpers as talks continue and has impressed manager Phil Brown as the Roots Hall side prepare for life in the National League next season.
And Brown is hopeful an agreement can reached with the forward this week.
Speaking to the Southend Echo, he said: ‘It’s still in the throws of the chairman giving it the nod,’ said Brown.
‘Ricky has impressed me with his attitude and mentality but that’s always been the case with him.
‘I’m hoping we will be able to sit down and get a deal drafted up tomorrow.’
Holmes made 14 appearances for Southend after signing for his home-town club in February.
He played 62 times for Pompey during his one-and-a-half years with the PO4 outfit, scoring twice.