Smart Cities and Virtual Reality technologies are at the centre of many scientific and political discourses and are generally presented as among the major technological innovations of our time. This chapter aims to investigate the relationship between cities and VR and, in particular, how urban spaces are represented through VR technologies. This chapter, hence, presents an overview of the VR representations of urban spaces, both providing an overview of the current state of urban representation in virtual reality contexts and identifying the untapped semiotic and technological potential in building urban VR experiences. To do so, we utilized a scoping method in order to collect a representative depiction of the entire field. A total of 37 applications containing both games and non–game apps were documented and analysed, yielding classification of both the cities therein and the users’ roles relative to them. An interdisciplinary methodology focusing on the semiotics and affordances of the titles analysed, allowed us to create several concepts and typologies to engage VR spaces. Clear trends emerged from the analyses, indicating patterns in the interconnection of the purpose of the application, the presented city, and the presented user or citizen. However, considering the vast potential of digital environments, and immersive virtual reality in particular, it is dejecting to see that these applications are mostly simplistic and are far from utilizing all of the potential affordances of (digital) cities and of the ever–improving technology. With this potential in mind, we present this study as a starting point for enriching similar applications and several points for consideration depending on its type and purpose. Finally, possible future research directions that would delve deeper in different segments of the field are briefly noted.