This study describes the cross-sectional prevalence of symptoms associated with eczema (chronic itchy rash), asthma (wheeze), and allergic rhinitis (rhinoconjunctivitis) in 1026 subjects between 18.5 and 23 months old (median age is 21 months) in Singapore. The first 2 yr cumulative prevalence of chronic itchy rash, wheeze, and rhinoconjunctivitis were 22.1% (n = 227), 22.9% (n = 235), and 8.4% (n = 86) respectively. In total, 42.2% (414 of 979) reported ever having any of these symptoms. Eczema, although prevalent, was diagnosed only in 34.4% (n = 78) of children with chronic itchy rash. Children with this eczematous rash were also more prone to wheeze (cOR = 2.0, 95% CI: 1.2–3.0) and rhinoconjunctivitis (cOR = 2.0, 95% CI: 1.4–2.8). Similarly, subjects who reported rhinoconjunctivitis and chronic itchy rash were 2.4 times (95% CI: 1.6–3.6) and 1.4 times (95% CI: 1.0–2.0) more at risk of wheezing respectively. Family history of allergy was a significant risk factor for chronic itchy rash (aOR = 1.8, 95% CI: 1.3–2.4) and wheeze (aOR = 1.7, 95% CI: 1.3–2.4). Thus, symptoms related to allergy were already prevalent during the second year of life. Significant proportions of these symptoms are likely to be due to true atopy as strong relationship with familial history and comorbidity with other potential allergic symptoms were observed.