The 20-year-old, who came up through the Sheffield United Academy and had an eight-year stint with the Blades, enjoyed a spell at fellow Northern Premier League side Gainsborough Trinity last season.
During his time at the Holy Blues, Conway scored once in 20 appearances.
He has also attracted the attention of League Two Doncaster Rovers in the past, having trialled with them whilst at his first senior club, Rossington Main.
After his time at Rossington, the midfielder joined Alfreton Town and went on to spend three years with the National League North side.
Conway gained the nickname Mascher from previous team-mates, with his playing style likened to former Liverpool and Barcelona midfielder Javier Mascherano.
“This is a great opportunity for me to show what I can do," he said.
"I had a taste of the play-offs with Gainsborough last season and I want more of that.
“I still have ambitions to play in the Football League and I feel that playing as many games as I can with Guiseley and helping to get them promoted would also help my own career."
Photo credit: Guiseley