Four species of Ciboneya Pérez, n. gen. are described from western Cuba: C. nuriae, n. sp. from La Habana and Pinar del Rio Provinces, C. odilere, n. sp., C. parva, n. sp., and C. antraia, n. sp. from Pinar del Rio Province. The species share apophyses on the male cheliceral fangs, corresponding pockets or modified areas on the female epigynum, and several details of the male pedipalps. Vertical hairs on the tibiae and metatarsi of the male legs and a retrolateral coxa apophysis on the male palp place the genus close to other Central and South American genera of the New World clade of pholcids, but the exact sister group is obscure. The spiders live in the leaf litter and under rocks in humid forests, or near the floor in caves. The females of C. antraia show a remarkable dimorphism in their genitalia, with rare intermediate forms. The possibly more frequent occurrence of such a dimorphism and the probable bias toward reporting it as two different species are discussed.