The combination of increasing costs, climate change, and disease- and pest-related issues present large challenges for the strawberry (Fragaria ×ananassa) industry in the United States. This is especially true for the Southeast, where rain, frost, and a range of foliar, fruit, and soil-borne diseases are prevalent, leading to significant losses every year. Simultaneously, niche winter markets open the opportunity to extend the harvest season, leading to an industry push to use protected culture strawberry production. Tabletop soilless strawberry greenhouse production has the advantage of avoiding soilborne issues while at the same time mitigating weather-related impacts on strawberry yield and quality. The use of long-day cultivars, originally bred for the Central Coast region of California, is currently the industry standard because of desired winter yields. However, short-day cultivars bred for Florida production might also have the potential to produce in winter. In this study, we evaluated the growth, yield, fruit chemistry, and fruit firmness of seven strawberry cultivars that are commonly grown in protected culture in North Carolina: Albion, Brilliance, Camino Real, Fronteras, Monterey, Florida Sensation, and Sweet Charlie. Experiments were conducted in a randomized complete block design in a commercial tabletop greenhouse in eastern North Carolina over two growing seasons (2022–23 and 2023–24). Our results showed that Florida cultivars Brilliance and Florida Sensation produced more consistently yields in winter compared with long-day cultivars Albion and Monterey and produced similar yields over the entire season. ‘Brilliance’ especially showed high fruit firmness across both years, and high sweetness in one of the two years. Additionally, the short-day cultivar Fronteras showed high yields in early spring and could serve as a late-season crop for direct-to-consumer producers. Our study showed that ‘Brilliance’ and ‘Florida Sensation’ could be alternatives to ‘Albion’, and that ‘Monterey’ can be used to produce a winter crop in a soilless tabletop production system in the Southeast.