This study was conducted to determine the volatile organic compounds (VOCs) associated with fruit flavor in diverse tomato cultivars (salad and cocktail cultivars) under organic low-input production. For this objective, 60 cultivars deriving from very diverse breeding programs 1880–2015 were evaluated in 2015, and a subset of 20 cultivars was selected for further evaluation in 2016. The diversity of instrumentally determined traits, especially for VOCs concentration and sensory properties (fruit firmness, juiciness, skin firmness, sweetness, sourness, aroma, and acceptability), was investigated at two harvest dates. The evaluation of the cultivars exhibited a wide range of variation for all studied traits, with the exception of a few VOCs. Cultivar had the most important effect on all instrumentally determined traits, while the influence of cultivar × harvest date × year interaction was significant for 17 VOCs, but not for total soluble solid (TSS) and titratable acidity (TA). The VOCs with the highest proportion (>8%) were hexanal, 6-methyl-5-heptene-2-one, 2-isobutylthiazole, and (E)-2-hexenal, which were identified in all cultivars. Twelve VOCs significantly correlated with one or more sensory attributes and these VOCs also allowed differentiation of the fruit type. Among these VOCs, phenylethyl alcohol and benzyl alcohol positively correlated with acceptability in the cocktail cultivars, whereas 2-isobuthylthiazole and 6-methyl-5-hepten-2-ol negatively correlated with acceptability in the salad cultivars. As a result of this study, organic breeders are recommended to use cultivars from a wide range of breeding programs to improve important quality and agronomic traits. As examples, salad tomatoes “Campari F1”, “Green Zebra”, and “Auriga”, as well as cocktail tomatoes “Supersweet 100 F1”, “Sakura F1”, and “Black Cherry” showed higher scores for the sensory attributes aroma and acceptability under organic low-input growing conditions. It remains a challenge for breeders and growers to reduce the trade-off of yield and quality.