It is intriguing to understand the influence of the watering volume and growing design on the growth, yield, and quality of cherry tomatoes. This study sought to identify the most effective watering volume and growing design treatment for the production and quality of the cherry tomato cultivar Ruby. This study was an exploration using a factorial experiment with an RCBD design. The treatment factors included the growing design (greenhouse, rain shelter, and screen house) and the watering volume (100% ETc, 75% ETc, and 50% ETc). The results showed that the root dry weight and root–shoot ratio were higher in the screen house design, while the fruit firmness was higher in the rain shelter design. Considering the effect of the watering volume, a higher fruit diameter, heavier fruits, more fruits per plant, higher ultimate fruit and biological yield per plant, higher root and shoot biomass, better root–shoot ratio, higher leaf chlorophyll content, greater fruit skin firmness, and greater elasticity were noted for the 100% ETc treatment. In contrast, the growth rate was higher for the 50% ETc treatment. Cultivating cherry tomatoes in a greenhouse using a watering volume of 100% ETc is recommended based on the results. These conditions led to better growth, higher fruit yield, and improved fruit quality, making them favorable options for successful cherry tomato production.