We study a system composed of like-charged cylinders and dumbbell-like counterions, with the focus laid on the role of the internal structure of counterions, using Monte Carlo simulations. The dumbbell ions are found to exhibit novel counterion condensation behavior governed by their length. Effective electrostatic interactions mediated between charged parallel cylinders also turn out significantly different from the case of pointlike ions, as a result of the complex interplay between the spatially separated charge distribution in the dumbbell counterions, their orientation, and the curvature of the charged cylinder. We show that at a weak-to-moderate electrostatic coupling strength, where effective like-charge interactions are usually found to be repulsive, the intercylinder interaction can become attractive and display a distinctive sensitivity to the cylinder curvature and dumbbell size, proving the significant effect of ion structure.