For the first time, we present the process simulation and multiobjective optimization of the batch-reactor polyesterification of a library of biomass-derived renewable polyesters: poly(1,5-pentylene 2,5-furandicarboxylate) (PTF), poly(1,5-pentylene succinate) (PTS), and poly(1,5-pentylene 2,5-furandicarboxylate-co-1,5-pentylene succinate (PTFTS). The simulation environment was implemented in Aspen Plus, and the e-constraint method was employed for the optimization problem, considering two objective functions that maximize the number-average degree of polymerization (DPN) and minimize the heat duty Q. The performance of the biobased polyesters was compared to that of poly(ethylene terephthalate) (PET). The kinetic rate expressions were defined following the functional-group approach, and the parameters were estimated by fitting a polyesterification model found in the literature to the experimental data. The present work provides comprehensive fundamental information toward a feasible process design and scale-up of the esterification of biomass-derived products.