Cucumis sativusL.) and habanero pepper ( Capsicum chinenseJacq.) growers have observed increased crop yield by placing bees in close proximity to these vegetable crops. However, adding managed bees typically may not be feasible for small-scale farmers or homeowners. Limited studies have demonstrated the potential of pollinator-attracting plants to be used as a lure to enhance the visitation of pollinators to adjacent food crops. This study evaluated the potential of adding pollinator-attracting plants in close proximity to cucumber and habanero plants to improve yields by either establishing permanent perennial companion plantings adjacent to the crops or interplanting annual companion plants within the row anew with each crop. The perennial treatment group consisted of Phyla nodiflora(L.) Greene, Borrichia frutescens(L.) DC., Salvia farinaceaBenth. ‘Henry Duelberg’, and Eysenhardtia texanaScheele. The annual treatment group consisted of Cosmos bipinnatusCav., Zinnia× marylandicaD.M. Spooner, Stimart, & T. Boyle, Borago officinalisL., and Ocimum basilicumL. Multiple cropping cycles were initiated using both spring and fall seasons, and yield was assessed for three successive cropping cycles. Fruit quality was unaffected by pollinator-attracting companion plantings; however total and marketable yields were impacted. Cucumber yields were significantly ( P< 0.05) greater during fall harvests with annual companion plantings and with the second fall harvest in perennial companion plant plots. Perennial companion plots initially yielded less than control plots or annual companion plots due to the space allocated to the companion plantings and the fewer pollinators initially attracted to the plots compared with the annual companion plantings. When the perennial plots became more established, they resulted in similar yields as the annual companion planting plots. Although habanero yields were increased by annual companion plantings in spring and fall, cucumbers were unaffected by companion plantings in spring. This suggests a potential seasonality for the efficacy of some pollinator-attracting companion plantings for a given crop that could offer an opportunity to tailor companion plantings to attract specific pollinators at different times of the year.