Sosaewon and Villa D’este were built in the early of 16th and mid-of 16th each. Sosaewon was built based on the accommodation of topography of the surroundings whilst Villa D’este highlights the distinction of terrace and axis existed on the configuration of the grounds and natures. Both gardens have reflected the social and political influence in that period of constructing tat the builders had been through. These factors have been analyzed by iconological methodology to interpret the inherent meaning of the garden in philosophical, mythological, religious and Feng-shui context and discovered the interconnected relations between two gardens. The characteristic of Sosaewon’s space is based on the Mu-yi-gu-gok, which is derived from a Taoist, due to a builder’s Neo-Confucianism value. Hence Sosaewon contains the adaption of the nature itself based on the values of Mu-yi-gu-gok, which are expressed by visual, auditory and literary elements, brining about the poetic beauty of waiting. The structures of Villa D’este reveal the combination of nature and art whilst it also connotes the theme of ‘The Choice of Hercules’, indicating the builder’s philosophy and will symbolically. Each space of Villa D’este has diverse space for various interpretations followed by this theme. For the interpretation of meaning of Sosaewon and Villa D’este, Sosaewon has adapted the nature of surroundings which contain a view of nature, on the other hand, Villa D’este borrowed the nature of surroundings to build and decorate the garden, using natural terrace and axis for the variation, and drag the river near the garden artificially to fit into the axis of the garden. Villa D’este contains significant mythological and iconological factor intended to highlight the builder’s dignity, status and position.