This paper introduces a methodology for predicting and mapping surface motion beneath road pavement structures caused by environmental factors. Persistent Scatterer Interferometric Synthetic Aperture Radar (PS-InSAR) measurements, geospatial analyses, and Machine Learning Algorithms (MLAs) are employed for achieving the purpose. Two single learners, i.e., Regression Tree (RT) and Support Vector Machine (SVM), and two ensemble learners, i.e., Boosted Regression Trees (BRT) and Random Forest (RF) are utilized for estimating the surface motion ratio in terms of mm/year over the Province of Pistoia (Tuscany Region, central Italy, 964 km2), in which strong subsidence phenomena have occurred. The interferometric process of 210 Sentinel-1 images from 2014 to 2019 allows exploiting the average displacements of 52,257 Persistent Scatterers as output targets to predict. A set of 29 environmental-related factors are preprocessed by SAGA-GIS, version 2.3.2, and ESRI ArcGIS, version 10.5, and employed as input features. Once the dataset has been prepared, three wrapper feature selection approaches (backward, forward, and bi-directional) are used for recognizing the set of most relevant features to be used in the modeling. A random splitting of the dataset in 70% and 30% is implemented to identify the training and test set. Through a Bayesian Optimization Algorithm (BOA) and a 10-Fold Cross-Validation (CV), the algorithms are trained and validated. Therefore, the Predictive Performance of MLAs is evaluated and compared by plotting the Taylor Diagram. Outcomes show that SVM and BRT are the most suitable algorithms; in the test phase, BRT has the highest Correlation Coefficient (0.96) and the lowest Root Mean Square Error (0.44 mm/year), while the SVM has the lowest difference between the standard deviation of its predictions (2.05 mm/year) and that of the reference samples (2.09 mm/year). Finally, algorithms are used for mapping surface motion over the study area. We propose three case studies on critical stretches of two-lane rural roads for evaluating the reliability of the procedure. Road authorities could consider the proposed methodology for their monitoring, management, and planning activities.