| Oppenheimer Eye Clinic Pllc | Health Care and Social Assistance | $190,000 | $190,973 | 13 | <$5M |  AI Deep Dive |
| Yankee Freedom III LLC | Transportation and Warehousing | $188,750 | $191,340 | 22 | $5.6M | AI Deep Dive |
| Ibis Bay Restaurant and Beverage LLC | Accommodation and Food Services | $187,464 | $188,326 | 48 | $8.5M | AI Deep Dive |
| Mirage International INC | Accommodation and Food Services | $186,589 | $187,448 | 27 | $8.4M | AI Deep Dive |
| Danger Corporation | Transportation and Warehousing | $185,857 | $188,402 | 30 | $7.6M | AI Deep Dive |
| 37 Court Investment INC | Accommodation and Food Services | $185,523 | $189,898 | 23 | <$5M | AI Deep Dive |
| Sunset Party Cat, Inc. | Transportation and Warehousing | $184,861 | $186,006 | 32 | $8.1M | AI Deep Dive |
| Hemingway Rum Company, LLC | Manufacturing | $184,200 | $186,518 | 44 | $15.5M | AI Deep Dive |
| Keys Productions INC | Accommodation and Food Services | $183,900 | $184,922 | 47 | $5.8M | AI Deep Dive |
| Land & Sea Sports LLC | Real Estate and Rental and Leasing | $183,100 | $184,188 | 18 | $8.1M | AI Deep Dive |
| Land & Sea Sports LLC | Arts, Entertainment, and Recreation | $183,063 | $183,988 | 14 | <$5M | AI Deep Dive |
| Danger Corporation | Transportation and Warehousing | $183,055 | $184,291 | 30 | $7.6M | AI Deep Dive |
| At Home in Key West INC | Real Estate and Rental and Leasing | $183,035 | $184,601 | 11 | <$5M | AI Deep Dive |
| At Home in Key West Inc. | Real Estate and Rental and Leasing | $183,000 | $184,235 | 12 | <$5M | AI Deep Dive |
| Sunset Party Cat INC | Transportation and Warehousing | $182,790 | $183,557 | 32 | $8.1M | AI Deep Dive |
| Mangoes Restaurant LLC | Accommodation and Food Services | $182,300 | $184,366 | 23 | <$5M | AI Deep Dive |
| Charlie Mac's 404, LLC | Accommodation and Food Services | $180,117 | $0 | 33 | $5.9M | AI Deep Dive |
| Operation Kidd, LLC | Accommodation and Food Services | $180,060 | $181,683 | 28 | <$5M | AI Deep Dive |
| Pbp Marina Rd | Accommodation and Food Services | $179,200 | $181,540 | 48 | $8.5M | AI Deep Dive |
| Gulf Southern Construction Company Kw INC | Construction | $178,782 | $181,081 | 15 | <$5M | AI Deep Dive |
| Key West Art and Historical Society | Arts, Entertainment, and Recreation | $178,500 | $179,229 | 21 | N/A | AI Deep Dive |
| Sarah Luna INC | Accommodation and Food Services | $178,500 | $180,290 | 25 | <$5M | AI Deep Dive |
| Horay Restaurant Group LLC | Accommodation and Food Services | $176,867 | $179,510 | 43 | $7.6M | AI Deep Dive |
| Fishbusterz Retail LLC | Retail Trade | $175,480 | $177,703 | 15 | <$5M | AI Deep Dive |
| The Mel Fisher Maritime Heritage Society INC | Arts, Entertainment, and Recreation | $175,272 | $179,313 | 13 | N/A | AI Deep Dive |