The typological transformation of single-family houses in Riyadh from attached courtyards to detached setback houses has affected the inhabitants' outdoor experiences. Several studies have criticized the detached setback typology in Saudi society for lacking privacy between neighbors, creating outdoor spaces with poor usability, and increasing thermal stress between houses. Other studies have highlighted the importance of outdoor thermal comfort in improving inhabitants' quality of life. In the desert climate of Riyadh, 49.02% of the year is classified uncomfortable heat period. Thus, the importance of maintaining thermally comfortable outdoor spaces and recognizing families' privacy as a significant cultural desire motivated this study, which evaluated the universal thermal climate index (UTCI) temperatures in outdoor in the setback, courtyard, and multiple yards typologies. The findings highlighted lower UTCI temperatures in multiple yards cases compared with that in courtyard cases, whereas higher UTCI temperatures in setback cases in the daytime. UTCI temperatures in multiple yards were lower by 1.72–2.14 °C than in setback cases during the morning, by 0.73–0.76 °C at noon, and by 1.17–1.6 °C in the afternoon. These findings support the argument for revising setback regulations to increase thermal comfort and the quality of life for inhabitants.