The evolutionary history of Axiokebuita and Speleobregma, two poorly known lineages of annelids exclusive from deep-sea or marine caves but always from crevicular habitats, is explored here. Speleobregma lanzaroteum Bertelsen, 1986, and Axiokebuita cavernicola sp. n. are described from anchialine and marine caves of the Canary Islands using light and electron microscopy. Speleobregma lanzaroteum is previously known only from a single specimen from the water column of an anchialine cave in Lanzarote. Emended diagnosis, details on the ciliary patterns and behavioural observations are provided based on newly collected material and in situ observations. Axiokebuita cavernicola sp. n. is found in Pleistocene gravel deposits in a shallow water marine cave in Tenerife (Canary Islands). The new species is characterized by the presence of dorsal ciliary bands and short knob-like neuropodial cirri from segment two. The porosity and permeability of the gravelly environment of A.cavernicola sp. n. are shown to be equivalent to the water column or crevices of Speleobregma and other Axiokebuita spp. Phylogenetic analyses of five gene fragments and 44 terminals using maximum-likelihood and Bayesian methods support a derived position of A.cavernicola sp. n. within Axiokebuita and confirm a sister-group relationship of Axiokebuita with Speleobregma with high nodal support. The Axiokebuita-Speleobregma clade is morphologically characterized by a globular pygidium with adhesive glands and ventral ungrooved ciliated palps. Our results support two independent cave colonization events, favoured by the preadaptation of the members of Axiokebuita-Speleobregma lineage to crevicular habitats.