Reproductive success within populations often varies with the timing of breeding, typically declining over the season. This variation is usually attributed to seasonal changes in resource availability and/or differences in the quality or experience of breeders. In colonial species, the timing of breeding may be of particular importance because the costs and benefits of colonial breeding are likely to vary over the season and also with colony size. In this study, we examine the relationship between timing of breeding and reproductive performance (clutch size and nest success) both within and between variable sized colonies (n∈=∈18) of fairy martins, Petrochelidon ariel. In four of these colonies, we also experimentally delayed laying in selected nests to disentangle the effects of laying date and individual quality/experience on reproductive success. Within colonies, later laying birds produced smaller clutches, but only in larger colonies. The general seasonal decline in nest success was also more pronounced in larger colonies. Late laying birds were generally smaller than earlier laying birds, but morphological differences were also related to colony size, suggesting optimal colony size also varies with phenotype. Experimentally delayed clutches were larger than concurrently produced non-delayed clutches, but only in larger colonies. Similarly, delayed clutches were more likely to produce fledglings, particularly later in the season and in larger colonies. We suggest that the reduced performance of late breeding pairs in larger colonies resulted primarily from inexperienced/low quality birds preferring to settle in larger colonies, possibly exacerbated by an increase in the costs of coloniality (e.g., resource depletion and ectoparasite infestations) with date and colony size. These findings highlight the importance of phenotype-related differences in settlement decisions and reproductive performance to an improved understanding of colonial breeding and variation in colony size.