The present study assessed the responses, in terms of vegetative, productive, qualitative, and nutritional features, of plants and berries of three remontant strawberry cultivars cultivated in soil and irrigated using three irrigation regimes: standard irrigation regime (W100), 20% (W80) less irrigation than the standard irrigation, and 40% (W60) less irrigation than the standard irrigation. The tested plants were “Albion”, “San Andreas”, and “Monterey”, which were cultivated in the east coast area of Marche, Italy. Specifically, the study examined the response of the genotype to irrigation deficit, highlighting the performance of the “Monterey” cultivar, which showed improvement in terms of fruit firmness, folate content, and antioxidant capacity at the W80 irrigation regime without a significant yield reduction. In all the cultivars, when irrigation was reduced by up to 20% of the standard irrigation regime (W100), there were no significant losses of yield or reduction in the fruits’ sensorial quality or antioxidant activity. The results showed that the standard irrigation regime (W100) commonly adopted by the farmers in the Marche area uses more water than necessary. With more accurate water management, it will be possible to save almost 226 m3 of water per hectare per cultivation cycle.