| Islamorada Lodge No. 2151, Loyal Order of Moose, Inc. | Other Services (except Public Administration) | $37,629 | $37,899 | 7 | <$5M |  AI Deep Dive |
| Wave Link Corp of Puerto Rico | Information | $37,185 | $37,435 | 6 | <$5M | AI Deep Dive |
| Island Community Church, Inc. | Other Services (except Public Administration) | $36,845 | $37,156 | 6 | N/A | AI Deep Dive |
| Angler House Marina, LLC | Arts, Entertainment, and Recreation | $36,600 | $36,876 | 6 | <$5M | AI Deep Dive |
| Habanos Ocean Front Corp | Accommodation and Food Services | $36,333 | $36,807 | 16 | <$5M | AI Deep Dive |
| Freewheeler Vacations, Inc. | Real Estate and Rental and Leasing | $35,265 | $35,572 | 4 | <$5M | AI Deep Dive |
| Islamorada Lodge No 2151 | Other Services (except Public Administration) | $35,189 | $35,414 | 5 | <$5M | AI Deep Dive |
| Island Aluminum of the Keys, Inc. | Construction | $33,853 | $34,280 | 5 | <$5M | AI Deep Dive |
| Bob's Bunz, Inc. | Accommodation and Food Services | $33,100 | $33,389 | 9 | <$5M | AI Deep Dive |
| Ragged Edge Resort, LLC | Accommodation and Food Services | $33,067 | $33,507 | 6 | <$5M | AI Deep Dive |
| Brett a Newman PA | Real Estate and Rental and Leasing | $32,500 | $32,865 | 2 | <$5M | AI Deep Dive |
| Coral Bay Marina Inc. | Other Services (except Public Administration) | $31,500 | $37,476 | 6 | <$5M | AI Deep Dive |
| Johnson Surveying & Construction Servicesinc | Professional, Scientific, and Technical Services | $31,464 | $31,630 | 2 | <$5M | AI Deep Dive |
| White Gate Court, Inc. | Accommodation and Food Services | $30,495 | $30,852 | 4 | <$5M | AI Deep Dive |
| Marshall Capital Solutions LLC | Finance and Insurance | $30,301 | $30,507 | 3 | <$5M | AI Deep Dive |
| Twisted Shrimp LLC | Accommodation and Food Services | $30,000 | $30,263 | 6 | <$5M | AI Deep Dive |
| Finatix Sportfishing of the Upper Keys, LLC | Arts, Entertainment, and Recreation | $30,000 | $30,241 | 2 | <$5M | AI Deep Dive |
| Southern Diversion One LLC | Accommodation and Food Services | $28,356 | $28,594 | 2 | <$5M | AI Deep Dive |
| Ricky's Holdings, LLC | Management of Companies and Enterprises | $28,267 | $28,470 | 6 | <$5M | AI Deep Dive |
| Patti Stanley LLC | Real Estate and Rental and Leasing | $28,229 | $28,619 | 5 | <$5M | AI Deep Dive |
| Cococnut Cove Resort & Marina INC | Accommodation and Food Services | $28,030 | $28,430 | 7 | <$5M | AI Deep Dive |
| Ross Early | Arts, Entertainment, and Recreation | $27,853 | $27,997 | 2 | <$5M | AI Deep Dive |
| Fjz Inc. | Other Services (except Public Administration) | $27,648 | $27,820 | 3 | <$5M | AI Deep Dive |
| S & S Performance INC | Other Services (except Public Administration) | $26,568 | $26,946 | 5 | <$5M | AI Deep Dive |
| Sea Dragon Tropical Asian Decor | Retail Trade | $26,400 | $26,638 | 4 | <$5M | AI Deep Dive |