Brazil is one of the centers of diversity of Cactaceae, yet studies addressing both pollination biology and the breeding system in Brazilian cacti are scarce. We herein present a detailed analysis of two native species with economic relevance: Cereus hildmannianus and Pereskia aculeata. The first species produce edible, sweet, spineless fruits and the second species produces leaves with high protein content. Pollination studies were undertaken through fieldwork observations in three localities of Rio Grande do Sul, Brazil, over two flowering seasons, totaling over 130 observation hours. Breeding systems were elucidated utilizing controlled pollinations. Cereus hildmannianus is solely pollinated by nectar-gathering species of Sphingidae hawk moths. In contrast, the flowers of P. aculeata are pollinated by predominantly native Hymenoptera but also by Coleoptera and Diptera, which gather pollen and/or nectar. Both cacti species are pollinator-dependent; neither intact nor emasculated flowers turn into fruit, yet whereas C. hildmannianus is self-incompatible, P. aculeata is fully self-compatible. In sum, C. hildmannianus is more restrictive and specialized regarding its pollination and breeding system, whereas P. aculeata is more generalist. Understanding the pollination needs of these species is a necessary starting point towards their conservation but also for their proper management and eventual domestication.