| Habitat for Humanity of the Upper Keys | Health Care and Social Assistance | $35,000 | $35,172 | 3 | N/A |  AI Deep Dive |
| Bayside Marine Canvas Upper Keys, LLC | Manufacturing | $34,810 | $35,098 | 6 | <$5M | AI Deep Dive |
| Largo Cargo Company | Retail Trade | $34,600 | $34,898 | 4 | <$5M | AI Deep Dive |
| Reef Title Company LLC | Professional, Scientific, and Technical Services | $34,563 | $34,761 | 3 | <$5M | AI Deep Dive |
| Degraaft INC | Manufacturing | $34,500 | $34,799 | 5 | <$5M | AI Deep Dive |
| Kinder in the Keys, Inc. | Finance and Insurance | $34,337 | $34,730 | 8 | <$5M | AI Deep Dive |
| Critters of the Keys INC | Retail Trade | $34,300 | $34,801 | 8 | <$5M | AI Deep Dive |
| Dps Home Construction Inc. | Construction | $34,000 | $34,445 | 3 | <$5M | AI Deep Dive |
| Montessori Academy of the Upper Keys LLC | Health Care and Social Assistance | $33,871 | $34,159 | 9 | <$5M | AI Deep Dive |
| Kona Kai Resort Management Group LLC | Accommodation and Food Services | $33,700 | $34,146 | 6 | <$5M | AI Deep Dive |
| Homepro Inspections of the Keys INC | Unknown | $33,582 | $33,857 | 3 | N/A | AI Deep Dive |
| Oru Associates, Inc. | Real Estate and Rental and Leasing | $33,300 | $33,775 | 1 | <$5M | AI Deep Dive |
| Key Largo Resort LLC | Accommodation and Food Services | $33,257 | $33,563 | 22 | $6.9M | AI Deep Dive |
| The Insurance Connection of South Florida, Inc. | Finance and Insurance | $33,252 | $33,601 | 6 | <$5M | AI Deep Dive |
| Emocean Sports, INC | Arts, Entertainment, and Recreation | $33,240 | $33,555 | 15 | <$5M | AI Deep Dive |
| Emocean Sports, INC | Retail Trade | $33,240 | $33,426 | 4 | <$5M | AI Deep Dive |
| Seaside Chiropractic, Inc. | Health Care and Social Assistance | $33,000 | $33,219 | 7 | <$5M | AI Deep Dive |
| Reef Title Company LLC | Real Estate and Rental and Leasing | $32,500 | $32,712 | 4 | <$5M | AI Deep Dive |
| Sea Dwellers Dive Center INC | Educational Services | $32,465 | $32,623 | 8 | <$5M | AI Deep Dive |
| Allen Funeral Directors LLC | Other Services (except Public Administration) | $32,242 | $32,478 | 6 | <$5M | AI Deep Dive |
| The Hidden Out Restaurant Inc. | Accommodation and Food Services | $32,028 | $32,322 | 5 | <$5M | AI Deep Dive |
| Juan Velizaroff Lawn Service, Inc. | Administrative and Support and Waste Management | $31,983 | $32,345 | 7 | <$5M | AI Deep Dive |
| David B Wilson | Finance and Insurance | $31,900 | $32,259 | 2 | <$5M | AI Deep Dive |
| Tolley & Hill Pllc | Professional, Scientific, and Technical Services | $31,900 | $32,245 | 3 | <$5M | AI Deep Dive |
| David Wilson | Finance and Insurance | $31,900 | $32,144 | 1 | <$5M | AI Deep Dive |