Despite being located in Winter Haven, Jessie's is more like a bar you'd find in Ybor. It caters to a younger crowd than the other neighborhood bars. The inside is classy looking with a wood bar and brick walls. Artwork done by local artists decorates the walls, and they frequently have art shows. Different local musicians play on Friday and Saturday night. They also have a full bar and happy hour everyday from 2 p.m.-6 p.m.