Highly porous functional scaffolds were obtained from linear and cross‐linked multifunctional poly(ε‐caprolactone) and poly(L‐lactide). The polymers were synthesized by ring‐opening polymerization of ε‐caprolactone and L‐lactide using poly(but‐2‐ene‐1,4‐diyl malonate) (PBM) as macroinitiator and stannous 2‐ethylhexanoate. The presence of a double bond in each repeating unit of PBM enabled cross‐linking of both scaffolds and films. Soft and flexible scaffolds were created from cross‐linked PBM. The mechanical properties of scaffolds and films were evaluated under cyclic conditions, with a focus on the compositions and molecular weights. It was obvious that PBM in the polymers and its cross‐linking ability resulted in tunable material characteristics, including an increased ability to recover after repeated loading.