Variation in intrinsic (body mass, reproductive condition) and extrinsic factors (habitat quality, spatiotemporal variation in food availability) can affect the costs and benefits of personality traits. Relationships between personality and fitness components can vary with changes in population density and/or habitat quality. Here, using capture-mark-recapture data of individually marked Eurasian red squirrels (Sciurus vulgaris), we explored whether indices of boldness and exploration are correlated with local survival in either of the sexes and with a measure of reproductive success in females, under different conditions of food availability. PCA scores derived from the number of captures (trappability) and number of different traps where an individual was captured (trap diversity), in the first one or two years of presence, were used as indices of personality (boldness and pure exploration). The relationships between boldness and local survival differed between habitats in both sexes. Bold squirrels survived better than shy ones in Norway spruce forest, while in the other two study areas (Scots pine, or mixed spruce-fir forest) survival was lower for bolder squirrels. Pure exploration behavior was negatively correlated with local survival in all habitats and in both sexes. Female reproductive success increased with body mass and decreased with the tendency to explore, a relationship consistent across habitat types. Bolder females did not have a reproductive advantage in years of poor food availability. We suggest that costs and benefits of boldness vary with spatio-temporal differences in availability of high-quality food resources which may help to maintain variation in personality in red squirrels in heterogeneous landscapes.