A leash caddy system for use with a retractable leash is provided. The retractable leash has a handle. The system comprises a cover with an attachment mechanism secured to the cover for releasably securing the cover around the retractable leash through the handle of the retractable leash. A plurality of guide hoops is mounted to the cover. A first securement mechanism associated with a first guide hoop and a fourth guide hoop secures the cover about the retractable leash. A second securement mechanism associated with the second guide hoop and the fourth guide hoop secures the cover about the retractable leash. Upon securing the cover about the retractable leash, the cover forms a pocket for receiving the cover therein.