Strawberry transplants produced in nurseries across Canada, northern United States, and California are shipped annually to other strawberry-growing regions, including Florida. Botrytis cinerea, the causal agent of gray mold, causes latent infections on transplants which are suggested as a potential source of primary inoculum in strawberry fields. In this study, we investigated the survival of B. cinerea isolates over the summer in Florida, the presence of B. cinerea in transplants from 14 nurseries from Canada and the United States in 2011, 2012, and 2013, and the sensitivity of nursery population to several botryticides. Botrytis cinerea was detected on dead strawberry plants sampled from commercial strawberry fields between March and June but not in July and August, suggesting that the fungus does not over-summer in strawberry fields in Florida. Nursery transplants surveyed in 2011, 2012, and 2013 showed B. cinerea incidences of 20 to 37, 20 to 83, and 2.5 to 92.5%, respectively. In total, 409 isolates were tested for sensitivity to pyraclostrobin, boscalid, pyrimethanil, fenhexamid, iprodione, penthiopyrad, fluopyram, and fludioxonil. Overall, respective resistance frequencies were 91.7, 79.3, 33.2, 20.7, 2.4, 0.2, 0.2, and 0.0%. A majority of isolates tested were resistant to either 3 or 4 fungicides simultaneously. These findings reinforce the need for an integrated approach between strawberry nurseries and production fields to improve gray mold management and mitigate future risks of resistance development in B. cinerea.