The landscape surrounding a summer villa is, in a morphological and experiential sense, an inseparable part of the villa and its garden. This research examines the level of preservation of the historic landscapes of eight summer villas in Dubrovnik and the level of their integration into the urban fabric of the contemporary city. The research methods used include the analysis of the relevant scientific literature as well as the analysis and interpretation of graphic materials, i.e., cadastral maps from the second half of the 19th century, orthophoto maps, and spatial planning documentation. In this paper, the immediate landscape in close vicinity to the summer villas is defined as the protective zone of a summer villa (PZSV). Although the original use and extent of the summer villa landscapes have rarely been preserved, it is possible to establish PZSVs in order to preserve, i.e., reinterpret, the setting of the summer villas, which is necessary to experience them in their totality. This research establishes the general principles that enable the identification of three general models of transformation of the summer villa landscape. Furthermore, this research develops possible scenarios for the enhancement of the summer villa landscape based on the identified models. These models and scenarios are generally applicable in the context of the protection and enhancement of the summer villa landscapes in of the south of Croatia.