Volatile compounds are essential for food organoleptic characteristics and of great utility for the food industry as potential markers for authenticity purposes (e.g., variety, geographical origin, adulteration). The aim of this study was to determine the characteristic volatile compounds of strawberry samples grown in a soilless system by using headspace solid phase micro-extraction coupled with gas chromatography and to investigate the influence of cultivar (Festival, Candonga, Camarosa) on this volatile profile. We observed that Festival and, to a lesser extent, Candonga varieties were characterized by the richest aroma-related profiles, including higher levels of esters, furanones and terpenes. In particular, methyl butyrate, hexyl hexanoate, linalool, geraniol and furaneol were the most abundant aromatic compounds detected in the three varieties of strawberries. Complementarily, the application of pattern recognition chemometric approaches, including principal component analysis and linear discriminant analysis, demonstrated that concentrations of specific volatiles can be employed as chemical descriptors to discriminate between strawberry cultivars. Accordingly, geraniol and hexyl hexanoate were found to be the most significant volatiles for the discrimination of strawberry varieties.