Habitat quality can have important consequences for avian communities through impacts on survival and annual reproductive success. However, habitat quality is often hard to measure, leading to the use of occupancy as a proxy. We compared habitat use of 5 avian species that used nest boxes in the oak woodlands of central coastal California, USA, to determine which habitat characteristics best predicted box occupancy. We focused on the relationship between habitat characteristics and occupancy for five species—Ash-throated Flycatcher (Myiarchus cinerascens), House Wren (Troglodytes aedon), Oak Titmouse (Baeolophus inornatus), Violet-green Swallow (Tachycineta thalassina), and Western Bluebird (Sialia mexicana)—for which we had 12 consecutive years of data on nest boxes spread over a 700 ha study area. We also examined whether the physical habitat characteristics and box occupancy rates were good predictors of reproductive success, to infer whether they were useful indicators of habitat quality. The habitat characteristics influencing nest-box occupancy differed among the 5 species. Ash-throated Flycatchers were associated with fragmented habitats with less grassland. House Wrens were associated with riparian vegetation, as were Oak Titmice, which were also associated with chaparral. Violet-green Swallows were associated with chaparral but tended to nest farther from riparian corridors than Oak Titmice. Western Bluebirds nested away from riparian corridors and in areas with more grassland and oak woodland. Finally, occupancy rate was a better predictor than habitat characteristics of reproductive success, which suggests that occupancy can be a valuable proxy for habitat quality for these 5 species.