Two new genera (Photeros and Enewton) and three new species of bioluminescent signaling ostracodes (Myodocopida: Cypridinidae) from Jamaica are described. They belong to a large cypridinid clade with male mating displays that we have found only in the Caribbean Sea. The species-specific displays and habitats in which each occurs are an integral part of each species definition. We postulate that the signaling clade has undergone rapid evolution driven by sexual selection particularly in Photeros Cohen and Morin, the only ostracode with both species-specific mating displays and clear species-specific morphological characters in the large male copulatory (eighth) limbs for each species (see also Morin and Cohen, 2010). Photeros comprises at least 19 species that are superficially somewhat similar in morphology (including 3 new species, all with authorship attributed to Morin and Cohen, 5 reassigned herein and 11 undescribed). The new Jamaican species are P. jamescasei, P. johnbucki, and P. mcelroyi. Species reassigned herein to Photeros are Vargula parasitica (with additional description based upon types and new Jamaican material), V. morini and V. annecohenae (from Belize), and V. graminicola and V. shulmanae (from Panama, with new information on lips and copulatory limbs). Photeros parasitica is a carrion feeder, not a parasite. We reassign Vargula harveyi to a new genus Enewton Cohen and Morin, with a more complete species description, including that of the previously unknown males and their bioluminescent mating displays. Morphological and display characters of genera and species are compared in tables. Homologies of morphological characters (some new), particularly in the upper lip, first antenna, seventh limb, and male eighth (copulatory) limb are described and discussed. Because signaling species are highly endemic, shallow signaling species are threatened by an increase in artificial lighting at night where their mating displays now occur. Videos of the displays from the three new species of Photeros are provided in the electronic accessory materials (Appendix 5).