| Perry F. Scuderi | Arts, Entertainment, and Recreation | $8,586 | $8,673 | 6 | <$5M |  AI Deep Dive |
| Michael Mccorkle | Construction | $8,586 | $8,636 | 1 | <$5M | AI Deep Dive |
| Frond + Feather Events, LLC | Other Services (except Public Administration) | $8,355 | $8,455 | 1 | <$5M | AI Deep Dive |
| Fishwife LLC | Transportation and Warehousing | $8,332 | $8,433 | 1 | <$5M | AI Deep Dive |
| New Barstan Holdings LLC | Accommodation and Food Services | $8,331 | $8,405 | 8 | <$5M | AI Deep Dive |
| Conch Property Managmnt INC | Administrative and Support and Waste Management | $8,262 | $8,326 | 2 | <$5M | AI Deep Dive |
| Florida Keys Fragrance & Gifts, LLC | Retail Trade | $7,595 | $7,678 | 1 | <$5M | AI Deep Dive |
| Reel Fishing INC | Administrative and Support and Waste Management | $7,500 | $7,563 | 1 | <$5M | AI Deep Dive |
| Thomas E Gibson Property Management of Islamorada LLC | Real Estate and Rental and Leasing | $7,272 | $7,341 | 3 | <$5M | AI Deep Dive |
| Nielsen Charters, Inc. | Health Care and Social Assistance | $7,222 | $7,267 | 1 | <$5M | AI Deep Dive |
| Earlybird Fishing Charters | Arts, Entertainment, and Recreation | $7,020 | $7,085 | 1 | <$5M | AI Deep Dive |
| Diana Lynne Smith | Arts, Entertainment, and Recreation | $7,006 | $0 | 1 | <$5M | AI Deep Dive |
| Murphy Charters INC | Arts, Entertainment, and Recreation | $6,937 | $7,010 | 1 | <$5M | AI Deep Dive |
| Murphy Charters INC | Arts, Entertainment, and Recreation | $6,937 | $6,966 | 1 | <$5M | AI Deep Dive |
| David T Sisung | Arts, Entertainment, and Recreation | $6,907 | $6,949 | 1 | <$5M | AI Deep Dive |
| Islamorada Running Company LLC | Arts, Entertainment, and Recreation | $6,695 | $6,759 | 2 | <$5M | AI Deep Dive |
| Island Stylin Inc. | Unknown | $6,667 | $6,716 | 1 | N/A | AI Deep Dive |
| Island Stylin INC | Transportation and Warehousing | $6,667 | $6,691 | 1 | <$5M | AI Deep Dive |
| Islamorada Investment Management, LLP | Finance and Insurance | $6,568 | $6,651 | 1 | <$5M | AI Deep Dive |
| Islamorada Restaurant and Bakery INC | Real Estate and Rental and Leasing | $6,559 | $6,625 | 2 | <$5M | AI Deep Dive |
| A Lil Tail Charters | Agriculture, Forestry, Fishing and Hunting | $6,413 | $6,436 | 1 | <$5M | AI Deep Dive |
| Barbara Cockerham | Manufacturing | $6,346 | $6,390 | 1 | <$5M | AI Deep Dive |
| Madeira Bay, Inc. | Real Estate and Rental and Leasing | $6,289 | $6,368 | 1 | <$5M | AI Deep Dive |
| Mary Cummings | Educational Services | $6,250 | $6,280 | 1 | <$5M | AI Deep Dive |
| Charli's Shave Ice | Accommodation and Food Services | $6,248 | $6,306 | 1 | <$5M | AI Deep Dive |