This study investigates the dynamic stiffness and damping characteristics of three polyurethane materials—PM, PS, and PST—using a comprehensive vibroacoustic testing approach. The aim is to examine material parameters such as dynamic stiffness, Young’s modulus, critical damping factor, and the influence of sample irregularities on the accuracy of measurements. The study employs both experimental testing, in which cuboidal and cylindrical polyurethane samples were subjected to sinusoidal excitation, and finite element modeling (FEM) to simulate the test conditions in sample without irregularities. Results indicate that sample contact surface irregularities (even as low as ~0.04 mm) significantly impact the measured dynamic stiffness, with the effect intensifying for materials with higher Young’s modulus values (above 5 MPa). Furthermore, cylindrical samples demonstrated more stable and repeatable measurements compared to cuboidal samples, where surface irregularities were tested in a more controlled environment. The findings underscore the need to consider sample geometry and irregularities in dynamic stiffness assessments to ensure better material evaluations. This work contributes valuable insights for the accurate modeling and testing of materials used in vibration isolation and sound insulation contexts.