A decarboxylative allylic benzylation cocatalyzed by Pd/photoredox in a regio- and enantioselective manner has been achieved. Readily available aryl acetic acids are used as benzylic nucleophile equivalents without preactivation. This mild and atom-economical protocol expands the scope of coupling partners of allylic electrophiles. Vinyl epoxides could also go through this transformation smoothly, affording various chiral homoallylic alcohols bearing all-carbon quaternary stereocenters.