| Jack Anderson | Retail Trade | $112,140 | $112,665 | 11 | <$5M |  AI Deep Dive |
| Local Color | Retail Trade | $112,140 | $113,046 | 13 | <$5M | AI Deep Dive |
| Captain Tony's Key West Bar INC | Accommodation and Food Services | $111,352 | $0 | 4 | <$5M | AI Deep Dive |
| Old Town Tavern LLC | Administrative and Support and Waste Management | $110,863 | $111,771 | 26 | <$5M | AI Deep Dive |
| Chef Distilled LLC | Accommodation and Food Services | $110,831 | $111,570 | 9 | <$5M | AI Deep Dive |
| Thirsty Mermaid, LLC | Accommodation and Food Services | $110,767 | $111,789 | 8 | <$5M | AI Deep Dive |
| Orbis Logistics Group LLC | Transportation and Warehousing | $110,048 | $110,949 | 5 | <$5M | AI Deep Dive |
| Engage Group LLC | Administrative and Support and Waste Management | $109,140 | $110,064 | 13 | <$5M | AI Deep Dive |
| Engage Group LLC | Administrative and Support and Waste Management | $109,139 | $110,033 | 12 | <$5M | AI Deep Dive |
| Kwja, Inc. | Real Estate and Rental and Leasing | $108,700 | $109,318 | 15 | $6.8M | AI Deep Dive |
| Eden House of Key West INC | Accommodation and Food Services | $108,610 | $110,031 | 17 | $5.3M | AI Deep Dive |
| Pinchers Crab Shack of Key West, INC | Accommodation and Food Services | $107,924 | $108,714 | 50 | $8.9M | AI Deep Dive |
| Habitat for Humanity of Key West and Lower Fl Keys | Health Care and Social Assistance | $107,600 | $108,189 | 5 | N/A | AI Deep Dive |
| United Street Trust LLC | Accommodation and Food Services | $107,527 | $108,507 | 5 | <$5M | AI Deep Dive |
| Reel Easy Charters | Transportation and Warehousing | $107,500 | $108,506 | 6 | <$5M | AI Deep Dive |
| Reel Easy Charters LLC | Real Estate and Rental and Leasing | $107,500 | $108,402 | 6 | <$5M | AI Deep Dive |
| New Moon Management Group, LLC | Real Estate and Rental and Leasing | $107,179 | $108,209 | 7 | <$5M | AI Deep Dive |
| Inzane Seafood Company INC | Wholesale Trade | $106,912 | $56,273 | 6 | <$5M | AI Deep Dive |
| Construction and Home Services | Construction | $106,693 | $107,631 | 13 | <$5M | AI Deep Dive |
| Purekw LLC | Real Estate and Rental and Leasing | $106,600 | $107,734 | 8 | <$5M | AI Deep Dive |
| Hibiscus Motel INC | Accommodation and Food Services | $106,381 | $107,226 | 10 | <$5M | AI Deep Dive |
| Radiology in Paradise LLC | Health Care and Social Assistance | $106,300 | $44,717 | 2 | <$5M | AI Deep Dive |
| Law Office of Manuel E. Garcia | Professional, Scientific, and Technical Services | $106,000 | $106,462 | 10 | <$5M | AI Deep Dive |
| The Pool Man of the Keys, LLC | Other Services (except Public Administration) | $105,980 | $106,675 | 9 | <$5M | AI Deep Dive |
| Jmd Development Inc. | Accommodation and Food Services | $105,298 | $106,310 | 22 | <$5M | AI Deep Dive |