Dennis Holloway (74), born and raised in Sanford, Florida, passed away at his home in Tavares, Florida on June 26, 2026, following a lengthy illness.

Dennis was a unique and special man with a true gift for making others laugh. Known for entertaining and playing pranks on co-workers, he had a seemingly endless supply of jokes and stories. He delighted in going to estate sales, yard sales, and thrift stores, and had a special knack for finding hidden treasures. A kind and compassionate man, Dennis enjoyed cooking and feeding others and helping people however he could. He was devoted to his two doodle dogs, and loved his family, especially his grandchildren, Leanna and Kaden.

Dennis was a Winn Dixie store manager in the Orlando and South Apopka areas for over 20 years, and the window and door installation manager for Probuild in Sanford until his retirement from the workforce in 2016. He was a proud veteran of the U.S. Army, having served in the Vietnam War from 1970 – 1973.

He is survived by his husband Michael Prestridge (Tavares); sons, Jason Holloway and Jeremy Holloway (Sanford); sister and brother-in-law, Diane and Rob Crews (Lake Mary), brother, Sherman Holloway (Deltona), sister-in-law, Dianne Holloway (Sanford), granddaughter, Leanna Holloway, grandson, Kaden Holloway, and numerous nieces, nephews, aunts, uncles and cousins. He is predeceased by his mother, Connie June Holloway (Miller), father, James Sherman Holloway, Sr., sister and brother-in-law, Joan and Steve Lynch, and brothers, Duane and Rick Holloway.

He will be missed and eternally loved by so many who knew him.