Dialdehyde sweet potato starch (DASS) with various aldehyde contents was prepared and the properties analyzed in terms of solubility, intrinsic viscosity, scanning electron microscopy (SEM), X-ray diffraction (XRD), and thermogravimetric analysis (TGA). The results demonstrated that when the aldehyede content of DASS was increased from 20% to 95%, the solubility, molecular weight, crystallizability, and thermal stability decreased. Thermoplastic DASS (TPDASS) was prepared by adding glycerol as a plasticizer; the thermal, rheological, hydrophobic, and tensile properties of TPDASS were investigated. The results indicated that, for the same glycerol content, with the increase of aldehyde content, the moisture adsorption decreased, while the shear viscosity, glass transition temperature, and tensile properties of TPDASS increased significantly. The effects were attributed to the introduction of aldehyde groups reducing the hydrogen bonds and decreasing the hydrophility of the starch. Moreover, the aldehyde and hydroxyl groups of DASS favored a semi-acetal formation with higher aldehyde content and cross-linking of DASS occurred with the increase of aldehyde content. In summary, compared to starch, the thermoplastic properties and hydrophobicity of DASS was improved. In the presence of water (10 wt%), the tensile strength of TPDASS with 95% aldehyde content (TPDASS95) moderately decreased, from 16.7 MPa to 14.0 MPa, when the glycerol content increased from 10% to 30%. The TPDASS with improved properties will find their applications in preparing biodegradable plastics.