Background: Evidence shows that HIV prevalence among young women in sub-Saharan Africa increases almost five-fold between ages 15 and 24, with almost a quarter of young women infected by their early-to mid-20s. Transactional sex or material exchange for sex is a relationship dynamic that has been shown to have an association with HIV infection. Methods: Using five focus group discussions and 19 in-depth interviews with young women enrolled in the HPTN 068 conditional cash transfer trial (2011-2015), this qualitative study explores young women's perceptions of transactional sex within the structural and cultural context of rural South Africa. The analysis also considers the degree to which young women perceive themselves as active agents in such relationships and whether they recognise a link between transactional sex and HIV risk. Results: Young women believe that securing their own financial resources will ultimately improve their bargaining position in their sexual relationships, and open doors to a more financially independent future. Findings suggest there is a nuanced relationship between sex, love and gifts: money has symbolic meaning, and money transfers, when framed as gifts, indicates a young woman's value and commitment from the man. This illustrates the complexity of transactional sex; the way it is positioned in the HIV literature ignores that "exchanges" serve as fulcrums around which romantic relationships are organised. Finally, young women express agency in their choice of partner, but their agency weakens once they are in a relationship characterised by exchange, which may undermine their ability to translate perceived agency into STI and HIV risk reduction efforts. Conclusions: This research underscores the need to recognise that transactional sex is embedded in adolescent romantic relationships, but that certain aspects make young women particularly vulnerable to HIV. This is especially true in situations of restricted choice and circumscribed employment opportunities. HIV prevention educational programmes could be coupled with income generation trainings, in order to leverage youth resilience and protective skills within the confines of difficult economic and social circumstances. This would provide young women with the knowledge and means to more successfully navigate safer sexual relationships.