Landscape urbanism suggests direction on the method of performing landscape through a practical strategy to deal with urban problems, by using landscape as a medium. However, even though such a practical topic has been advocated, failure to resolve the difference between theory and practice has been criticized. To identify the vagueness of the concept of landscape urbanism, this study aims to identify the differential properties of texts that appear in discourse. It analyzes the discourse on the word “landscape” and looks at the relation between texts and contexts that form the discourse from a semantic approach. The texts have been extracted from the discourse of Corner and Waldheim where their meaning and signification are derived through the contextualization and systematization of the word “landscape”. In landscape urbanism, the word “landscape” has a conceptual representation of the theory, and the textual context contained in “landscape” is complex and multi-layered. The major texts related to the word “landscape” have semantic relations that have denotative and connotative meaning. The affiliation with the subject of landscape relates to the denotative meaning, and the texts related to the properties of landscape have a connotative meaning. The lexicon of the word “landscape” is a complex system, which forms its signification through emergence and self-organization. Meanwhile, the word “landscape” has the individuality of texts in complicated relations, including inevitable vagueness and contingency, which limits the study in applying and evaluating the analysis objectively.