Molar mass-controlled dihydroxyl telechelic polylactide and polyhydroxybutyrate oligomers were synthesized by ring-opening polymerization or transesterification. These oligomers were used as soft segments in two-step allyl-functionalized poly(ester-urethane) syntheses. The expected structures were confirmed by 1 H nuclear magnetic resonance spectroscopy, size exclusion chromatography, and differential scanning calorimetric, and the obtained polyurethanes were copolymerized with 2-hydroxylethyl methacrylate. Thermal degradations of the dihydroxyl telechelic oligomers, double-bond functionalized poly(ester-urethane)s, and the issued networks were analyzed using thermogravimetry coupled by Fourier transform infrared spectroscopy analysis.