Determining the extent of repeatable differences in the behavior of animals and the factors that influence behavioral expression is important for understanding individual fitness and population processes, thereby aiding in species conservation. However, little is known about the causes of variation in the repeatability of behavioral differences among species because rarely have comparative studies been undertaken to examine the repeatability of behavioral differences among individuals within their natural ecological settings. Using two species of endemic subtropical anemonefishes, Amphiprion mccullochi and A. latezonatus at Lord Howe and North Solitary Islands, Australia, we conducted an in situ comparative analysis of personality traits, examining the repeatability of boldness, sociability and aggression as well as the potential role of environmental and social factors on behavioral expression. For A. mccullochi, only boldness and aggression were highly repeatable and these behaviors formed a behavioral syndrome. For A. latezonatus, none of the three behaviors were repeatable due to low-inter-individual variation in behavior. We suggest that the harsher and more variable environmental and social conditions experienced by A. latezonatus have resulted in reduced repeatability in behavior, in contrast to A. mccullochi which typically inhabits a more stable lagoonal reef environment. Additionally, group size and size rank, rather than nearest-neighbor distance and anemone size, influenced the expression of these behaviors in both species, suggesting that behavioral variation was more sensitive to social than environmental factors. Overall, differences in repeatability between these closely related species likely reflect adaptations to contrasting environmental and social conditions, although alternative explanations must be considered. The differences in behavioral consistency between these two endemic anemonefishes could lead to disparity in their resilience to environmental or social change in the future.