Lepidolejeunea grandiocellata, sp. nov. is described for two specimens from the Blue Mountains of Jamaica. This delicate species is characterized by ocelli in basal parts of leaves, underleaves, bracteoles and bracts often being conspicuously larger than the surrounding cells, whereas ocelli in central and upper parts of these structures are more or less the same size as surrounding cells. Further defining characters include sharply 5-keeled perianths without inflated horns, and orbicular underleaves with a sharp, v-shaped notch. In a molecular phylogeny based on the nrITS region and the cp DNA markers rbcL and trnL-F, L. grandiocellata is placed sister to a clade including accessions of L. delessertii from Reunion and accessions of L. cuspidata, L. eluta, and L. sullivantii from the Neotropics [L. subg. Perilejeunea]. Based on the phylogeny and the characters of the ocelli, L. grandiocellata is placed in a new subgenus Caribeolejeunea.