We report and describe the first sirenian endocranial casts from the West Indies based on three specimens collected from two quarries of the upper Oligocene–lower Miocene Colón Formation, in the province of Matanzas, western Cuba. We assign them to Dugongidae incertae sedis, based on a phylogenetic analysis of fossil and extant sirenians. Thus, these new specimens provide a unique opportunity to describe the endocranial neuroanatomy of this family. The endocasts are suggestive of dugongids with limited vision and olfaction, based on the diminished olfactory and optic nerves. Additionally, we provide a geological reinterpretation of the Colón Formation and its paleoecological setting. Altogether, these data provide further insight into the diversity and evolution of sirenians, especially Caribbean dugongs.