Grassland birds are globally imperiled. Those of endemic Neotropical savannas may be particularly threatened as knowledge of the ecology of many species is lacking, restricting our ability to take decisive conservation action. During the dry (non-breeding) season of 2010, we studied the population size, distribution, and habitat associations of the Cock-tailed Tyrant (Alectrurus tricolor), Black-masked Finch (Coryphaspiza melanotis), and Wedge-tailed Grass-finch (Emberiziodes herbicola) across a disturbance-mediated savanna–grassland gradient in Beni, Bolivia. We used distance sampling and surveyed structural and resource-specific habitat features at plots where birds were present versus random locations. Occupancy models identified fine-scale habitat associations. Cock-tailed Tyrant (7.1 ind./km2) specialized on open habitats in areas expected to be heavily inundated in the wet season, avoided trees, and selected tall grassy swards. Black-masked Finch (25.1 ind./km2) occurred across the gradient, associating with tall, forb-rich swards, sparse shrubs, and low levels of fruiting and seeding vegetation. Wedge-tailed Grass-finch (27.9 ind./km2) also occurred across the gradient, particularly associated with tall, forb-rich swards, abundant seeding grasses, and sparse shrubs. Our results offer the first quantitative abundance estimates for these species in Beni, provide vital baselines for future monitoring, and improve knowledge of the ecology and conservation management needs of these species. Importantly, our results suggest that populations of these three grassland birds may be best maintained in heterogenous, mosaic landscapes that can be produced by carefully managed burning and grazing. Further research in the breeding season would facilitate making stronger, more specific management recommendations.