A key to 17 species in the genus Hygrocybe, subgenus Pseudohygrocybe, sections Coccineae and Neohygrocybe sensu Boertmann is provided for the Greater Antilles. Five new species and five taxa that are new reports for the region are described. The new species in section Coccineae are H. pseudoadonis, H. viridiphylla, and H. zonata. The new species in section Neohygrocybe are H. albomarginata and H. ovinoides. The new reports are H. caespitosa, H. coccinea, H. cf. miniata, H. papillata, and H. subovina. Three new combinations are proposed: Hygrocybe mycenoides, H. papillata and H. subovina.