Symbiotic relationships between shrimps and other invertebrates are a very common phenomenon in tropical environments. Although the caridean shrimp-ascidian association has been known for many years, the nature of this relationship is still unclear. The current study investigated the association between the caridean shrimp Odontonia sibogae (Bruce, 1972) and solitary ascidians. A combination of field work conducted along the Red Sea coast of Israel and laboratory experiments, conducted during 2015–2016, revealed a clear preference of the shrimps for the ascidian species Herdmania momus (Savigny, 1816), with a low survival ability of the shrimp outside their host’s body. The shrimps usually inhabit their host as pairs of male and female or pair of females, but never as pairs of males. Out of the 53 studied females, 51% were observed to bear between 156–1,146 embryos, throughout the course of the year. As these ascidian hosts are known to create large aggregates, we suggest that males may possibly wander among the ascidians occupied by females in order to increase their reproductive success. To date, this is the first study to record the shrimp Dactylonia ascidicola (Borradaile, 1898) inhabiting the ascidian H. momus; and the first study to investigate in depth the ascidian-shrimp association in the Red Sea. It thus provides a platform for future research into the physiological and behavioral adaptations required for such a unique association.