On December 20, 2016, Holaday signed a minor league deal with the Philadelphia Phillies. After being informed that he would not make Philadelphia's roster to begin the season, Holaday opted out of his contract. On March 31, 2017, the Tigers signed Holaday to a minor league contract and assigned him to the Toledo Mud Hens. On September 1, the Tigers purchased Holaday's contract. At the time of his call-up, Holaday was hitting .269 with 12 home runs and 50 RBI in 93 games for Toledo. He was outrighted to Triple-A on November 3, and elected free agency on November 7. On December 1, 2017, Holaday signed a minor league contract with the Miami Marlins. Holaday's contract was purchased by the Marlins on March 28, 2018, and he was assigned to the Opening Day roster. He elected free agency on October 27. On November 26, Holaday re-signed with the Marlins to a minor league contract. He was released on March 23, 2019, after opting out of his contract. However, he re-signed to another minor league deal on March 26 to stay with the Marlins. He opened the 2019 season with the New Orleans Baby Cakes. Following the 2019 season, Holaday was outrighted off the Marlins roster and elected free agency on October 18. On January 13, 2020, Holaday signed a minor league deal with the Baltimore Orioles that included an invitation to spring training. Holaday's older brother, Bobby, also played for the baseball team at Warren Travis White High School.