In this paper we deal with the geography of pathways through homelessness, developed by households who live in holiday parks in the rural southern part of Belgium (Wallonia). The paper aims to provide insights into the motivations and objectives of the homeless themselves and to identify structural obstacles that risk reproducing homelessness. After a conceptual introduction, we present our research methodology, which combines quantitative and qualitative methods. The following section then briefly describes the socio-historical background of three permanently inhabited holiday parks, which serve as case studies for this paper. The empirical results focus on the geography of pathways, stressing housing situations before and beyond permanent habitation of holiday parks. We conclude by arguing that a collective and holistic policy is needed to fight homelessness.