Machine learning techniques are advancing rapidly in theoretical grounds, but their practical application and real evaluation in engineering disciplines are limited. This study investigates one-year of experimental data for indoor air conditions and energy monitoring of two identical portable cabins in Kuwait. Additionally, a 9-month period of solar photovoltaic energy production is experimentally obtained for assessing energy saving aspects of a solar assisted air conditioning system in one of the cabins. A transient system simulation tool model is developed and validated for the portable cabins. Both one-year experimental data and the validated simulation data are used for developing machine learning models for six case studies in Kuwait and Australia. In simulations, there are issues related to lack of access to real-time weather data from a locally installed weather station. In experimental works, there were issues related to disruption of data collection due to power or internet shutdowns. To resolve these issues, nineteen regression models are investigated. It was found that all models performed very well although the Matern 5/2 and Exponential gaussian process regression model performed slightly better, with all models achieving high accuracy, as indicated by R-squared values close to 1.0 in all six case studies. Overall, it was found that the photovoltaic solar-assisted air conditioning system could save annually 26.2 % and 75.7 % energy in Kuwait and Rockhampton, Australia, respectively.