| Barefoot Billy's, Inc. | Transportation and Warehousing | $126,600 | $128,284 | 26 | $6.6M |  AI Deep Dive |
| Barefoot Billy's Inc. | Retail Trade | $126,600 | $127,152 | 26 | $6.2M | AI Deep Dive |
| 913 Duval Street LLC | Accommodation and Food Services | $126,427 | $127,421 | 10 | <$5M | AI Deep Dive |
| Dsr1, LLC | Other Services (except Public Administration) | $125,900 | $126,799 | 14 | <$5M | AI Deep Dive |
| Key West Yacht Club Inc. | Arts, Entertainment, and Recreation | $125,100 | $126,306 | 12 | N/A | AI Deep Dive |
| Kw Five II LLC | Accommodation and Food Services | $125,000 | $126,319 | 21 | <$5M | AI Deep Dive |
| New Moon Management Group LLC | Administrative and Support and Waste Management | $123,999 | $124,424 | 6 | <$5M | AI Deep Dive |
| Law Office of Manuel E. Garcia | Professional, Scientific, and Technical Services | $123,800 | $124,912 | 12 | <$5M | AI Deep Dive |
| Md4er LLC | Unknown | $123,557 | $124,701 | 14 | N/A | AI Deep Dive |
| Spottswood, Spottswood, Spottswood & Sterling, Pllc | Professional, Scientific, and Technical Services | $123,414 | $124,681 | 7 | <$5M | AI Deep Dive |
| Spottswood Spottswood Spottswood & Sterling Pllc | Professional, Scientific, and Technical Services | $123,414 | $123,721 | 7 | <$5M | AI Deep Dive |
| Keys Iron Works, INC | Construction | $123,400 | $124,644 | 11 | <$5M | AI Deep Dive |
| Key Iron Works INC | Construction | $123,400 | $123,996 | 11 | <$5M | AI Deep Dive |
| Shs Hotel Investments of South Florida INC | Accommodation and Food Services | $123,345 | $123,744 | 8 | <$5M | AI Deep Dive |
| Pepper Shark LLC | Accommodation and Food Services | $122,891 | $123,423 | 19 | <$5M | AI Deep Dive |
| 425 Tacos LLC | Accommodation and Food Services | $121,639 | $122,192 | 16 | <$5M | AI Deep Dive |
| Zaraab, LLC | Unknown | $121,162 | $122,552 | 28 | N/A | AI Deep Dive |
| Liz Carpentry LLC | Construction | $120,500 | $121,514 | 15 | <$5M | AI Deep Dive |
| Samuel's House Inc. | Health Care and Social Assistance | $120,449 | $121,538 | 9 | N/A | AI Deep Dive |
| Douglas House INC | Accommodation and Food Services | $120,000 | $120,516 | 8 | <$5M | AI Deep Dive |
| Tejas LLC | Accommodation and Food Services | $120,000 | $120,870 | 10 | <$5M | AI Deep Dive |
| D&v Commercial Ac, INC | Construction | $119,797 | $120,880 | 10 | <$5M | AI Deep Dive |
| Key West Players Inc. | Arts, Entertainment, and Recreation | $119,400 | $120,004 | 8 | <$5M | AI Deep Dive |
| Key West Players, Inc. | Arts, Entertainment, and Recreation | $119,400 | $120,607 | 81 | $13.3M | AI Deep Dive |
| Womankind INC | Health Care and Social Assistance | $118,700 | $119,692 | 15 | N/A | AI Deep Dive |