The intent of this paper is to search for the significant landscape design elements of classical Roman Villa Suburbana appeared at the beginning of the first century A.D. Pliny the Younger was one of Roman statesman who was famous with his publications of nine books of literary letters. Among his letter were detail descriptions of the Laurentine Villa and the Tuscan Villa. These two villas are one of the oldest sources of information to study the evolvement and give influence to the history of garden design. This paper begins with the discussion of who is Pliny and how his letters are so important to the history of garden design. Then, it will continue with interpreting Pliny's letters for the Laurentine Villa and the Tuscan Villas, learning how the landscape context, the villas, the relationships between the villa and the garden, and the significant elements of the gardens are organized.