The preparation of polymers with high self-healing ability is conducive to environmental protection and resource conservation. In the present work, two kinds of polyurethane (PU) elastomers were prepared: the one containing flexible end blocks (polypropylene glycol) and the other containing flexible end blocks and 2-ureido-4[1H]-pyrimidinone (UPy) groups that can form reversible quadruple hydrogen bonds. Both of the two PU elastomers have self-healing ability. At low temperatures the PU without UPy groups exhibits stronger self-healing ability, while at high temperatures the PU with UPy groups has better self-healing function. The difference can be attributed to the combined effect of segmental mobility and reversible network strength. Based on molecular simulations, we further observed that the self-healing behaviors are affected by four factors: healing temperature, reversible interaction strength, reversible interaction site density and segment diffusion ability.