Purpose: To investigate the influence of shorter, more frequent rest breaks with per-cooling as an alternative heat-acclimation session on physiological, perceptual, and self-paced maximal cycling performance, compared with continuous heat exposure. Methods: Thirteen participants completed 1 continuous and 3 intermittent-heat-exposure (IHE) maximal self-paced cycling protocols in a random order in heat (36 °C, 80% relative humidity): 1 × 60-minute exercise (CON), 3 × 20-minute exercise with 7.5-minute rest between sets (IHE-20), 4 × 15-minute exercise with 5-minute rest between sets (IHE-15), and 6 × 10-minute exercise with 3-minute rest between sets (IHE-10). Mixed-method per-cooling (crushed-ice ingestion and cooling vest) was applied during rest periods of all IHE protocols. Results: Total distance completed was greater in IHE-10, IHE-15, and IHE-20 than in CON (+11%, +9%, and +8%, respectively), with no difference observed between IHE protocols. Total time spent above 38.5 °C core temperature was longer in CON compared with IHE-15 and IHE-20 (+62% and +78%, respectively) but similar to IHE-10 (+5%). Furthermore, a longer time above 38.5 °C core temperature occurred in IHE-10 versus IHE-15 and IHE-20 (+54% and +69%, respectively). Sweat loss did not differ between conditions. Conclusion: IHE with per-cooling may be a viable alternative heat-acclimation protocol in situations where training quality takes precedence over thermal stimulus or when both factors hold equal priority.