The article reveals some of the intricate relationships between urbanization at different stages, human horizontal (spatial) and partial vertical mobility, and changing ruralurban communities. After reviewing the key ideas and schools of urban and urbanization studies, the authors examine the conceptual diversity and many-sided nature of deurbanization as a spatial, societal and cultural-mental transformation. The controversial discourse of the latter, which often implies opposite approaches and phenomena, such as social lifting or downshifting, is stressed, along with the greater role of individual decisions. Stronger social and spatial links between cities and rural areas in the globalizing world manifest themselves in the accelerated formation of the rural-urban continuum and through the growing recurrent spatial mobility of people. Russia’s incomplete urbanization and polarization of its socio-economic space have created two massive opposite flows, i.e. the centrifugal seasonal dacha deurbanization and the centripetal labor migration of Russian villagers and small town dwellers towards large cities. The two streams are interrelated, e.g. temporal urban work, and the lodging of Russian otkhodniks instead of resettling, leading to the prolongation of the life of peripheral localities where their families stay. This habitability, in turn, facilitates the dacha development of small settlements. The article considers the reasons for “guest work” in Russian cities and the variety of dachas, as well as their impact on both urban and rural lifestyles. Mass movements of vacationers and workers and their two-house lives, sometimes balanced in time, complicates the knowledge of how many people actually live and work in the countryside, in small and big cities. This is a serious obstacle to the adequate maintenance and development of Russia’s spaces, since local budgets are designed for permanent population alone – which in many places is partially true.