Landscape stewardship offers a means to put social-ecological approaches to stewardship into practice. The growing interest in landscape stewardship has led to a focus on multistakeholder collaboration. Although there is a significant body of literature on collaborative management and governance of natural resources, the particular challenges posed by multifunctional landscapes, in which there are often contested interests, require closer attention. We present a case study from South Africa to investigate how collaborative stewardship can be fostered in contested multifunctional landscapes. We conducted this research through an engaged transdisciplinary research partnership in which we integrated social-ecological practitioner and academic knowledge to gain an indepth understanding of the challenges of fostering collaboration. We identified five overarching factors that influence collaboration: contextual, institutional, social-relational, individual, and political-historical. Collaborative stewardship approaches focused on the development of formal governance institutions appear to be most successful if enabling individual and social-relational conditions are in place. Our case study, characterized by high social diversity, inequity, and contestation, suggests that consensus-driven approaches to collaboration are unlikely to result in equitable and sustainable landscape stewardship in such contexts. We therefore suggest an approach that focuses on enhancing individual and social-relational enablers. Moreover, we propose a bottom-up patchwork approach to collaborative stewardship premised on the notion of pluralism. This would focus on building new interpersonal relationships and collaborative capacity through small collective actions. Taking a relational, pluralistic approach to fostering collaborative stewardship is particularly important in contested, socially heterogeneous landscapes. Drawing on our study and the literature, we propose guiding principles for implementing relational, pluralistic approaches to collaborative stewardship and suggest future research directions for supporting such approaches.