| Barefoot Painting Otlk | Construction | $20,833 | $16,091 | 1 | <$5M |  AI Deep Dive |
| Jane Marquis DBA Barnacle Bed & Breakfast | Accommodation and Food Services | $20,832 | $21,050 | 2 | <$5M | AI Deep Dive |
| Narciso Carrillo Rodriguez | Retail Trade | $20,800 | $21,098 | 1 | <$5M | AI Deep Dive |
| Fast Action Marine, Inc. | Retail Trade | $20,700 | $20,865 | 5 | <$5M | AI Deep Dive |
| Lower Keys Bobcat Svc INC | Professional, Scientific, and Technical Services | $20,600 | $20,866 | 4 | <$5M | AI Deep Dive |
| Maylin Lima | Professional, Scientific, and Technical Services | $20,560 | $20,621 | 1 | <$5M | AI Deep Dive |
| Edward Sommer | Accommodation and Food Services | $20,466 | $0 | 1 | <$5M | AI Deep Dive |
| Key West Visitors INC | Administrative and Support and Waste Management | $20,037 | $20,257 | 8 | <$5M | AI Deep Dive |
| Key West Visitors INC | Administrative and Support and Waste Management | $20,037 | $20,306 | 8 | <$5M | AI Deep Dive |
| Big Pine Key Restaurant INC | Accommodation and Food Services | $19,919 | $20,059 | 3 | <$5M | AI Deep Dive |
| My Keys Mobile Equipment and Trucking Repair | Other Services (except Public Administration) | $19,600 | $19,762 | 2 | <$5M | AI Deep Dive |
| Ting2019 Inc. | Accommodation and Food Services | $19,097 | $50,905 | 10 | <$5M | AI Deep Dive |
| Ichabod Crane Service Inc. | Manufacturing | $19,045 | $19,203 | 3 | <$5M | AI Deep Dive |
| Michael Hussey | Construction | $18,762 | $18,879 | 1 | <$5M | AI Deep Dive |
| Osvel Noa Pumariega | Construction | $18,712 | $18,794 | 1 | <$5M | AI Deep Dive |
| Ryan Phinney | Transportation and Warehousing | $18,500 | $18,727 | 1 | <$5M | AI Deep Dive |
| Denise M. Bays, Ea P.l. | Professional, Scientific, and Technical Services | $18,500 | $18,656 | 2 | <$5M | AI Deep Dive |
| Isla Nails, LLC | Finance and Insurance | $18,067 | $18,213 | 1 | <$5M | AI Deep Dive |
| William Cauthen LLC | Construction | $17,805 | $17,392 | 3 | <$5M | AI Deep Dive |
| Crystal Sizemore | Health Care and Social Assistance | $17,500 | $17,609 | 1 | <$5M | AI Deep Dive |
| Caregivers of the Keys Inc. | Administrative and Support and Waste Management | $17,493 | $17,656 | 3 | <$5M | AI Deep Dive |
| Big Pine Tax Service INC | Professional, Scientific, and Technical Services | $17,200 | $17,362 | 2 | <$5M | AI Deep Dive |
| Therapeutic Touch by Chrystal | Other Services (except Public Administration) | $17,000 | $17,127 | 1 | <$5M | AI Deep Dive |
| Rubio's Road Service, Inc. | Other Services (except Public Administration) | $16,727 | $16,851 | 3 | <$5M | AI Deep Dive |
| Barbara Mckee INC | Real Estate and Rental and Leasing | $16,700 | $16,877 | 1 | <$5M | AI Deep Dive |