| Simonton Court Management Company, INC | Accommodation and Food Services | $88,900 | $89,522 | 20 | $6.3M | AI Deep Dive |
| Seaside Pediatrics of Key West, Pllc | Health Care and Social Assistance | $88,893 | $89,862 | 8 | <$5M | AI Deep Dive |
| Seaside Pediatrics of Key West Pllc | Health Care and Social Assistance | $88,892 | $89,776 | 6 | <$5M | AI Deep Dive |
| Lazy Dog Adventures LLC | Administrative and Support and Waste Management | $88,767 | $89,302 | 10 | <$5M | AI Deep Dive |
| Certified Appliance Repair INC | Other Services (except Public Administration) | $88,200 | $89,278 | 8 | <$5M | AI Deep Dive |
| Aqsr Key West LLC | Accommodation and Food Services | $88,000 | $88,743 | 21 | <$5M | AI Deep Dive |
| Red Barn Actor's Studio, INC | Other Services (except Public Administration) | $87,900 | $89,028 | 20 | N/A | AI Deep Dive |
| Pepper Shark LLC | Accommodation and Food Services | $87,779 | $88,387 | 19 | <$5M | AI Deep Dive |
| Ich Key West, LLC | Accommodation and Food Services | $87,643 | $88,555 | 13 | <$5M | AI Deep Dive |
| Clean Cut of Key West, LLC | Professional, Scientific, and Technical Services | $87,500 | $0 | 11 | <$5M | AI Deep Dive |
| Key West Film Society, Inc. | Information | $87,500 | $88,492 | 8 | N/A | AI Deep Dive |
| Keys Armored Express INC | Transportation and Warehousing | $87,400 | $88,558 | 15 | <$5M | AI Deep Dive |
| The Loose Cannon Key West, LLC | Accommodation and Food Services | $87,352 | $88,616 | 19 | <$5M | AI Deep Dive |
| Ibiza Enterprises LLC | Accommodation and Food Services | $87,230 | $88,374 | 12 | <$5M | AI Deep Dive |
| The Bc Too LLC | Accommodation and Food Services | $87,200 | $87,698 | 20 | <$5M | AI Deep Dive |
| Misohappy LLC | Accommodation and Food Services | $87,013 | $87,499 | 46 | $8.2M | AI Deep Dive |
| General Horseplay LLC | Accommodation and Food Services | $86,900 | $87,219 | 16 | <$5M | AI Deep Dive |
| Total Temperature Control INC | Construction | $86,895 | $87,231 | 5 | <$5M | AI Deep Dive |
| Key West Harbor Services | Transportation and Warehousing | $86,800 | $87,174 | 6 | <$5M | AI Deep Dive |
| B&b Enterprises Key West LLC | Accommodation and Food Services | $86,574 | $87,473 | 12 | <$5M | AI Deep Dive |
| Grader Mike LLC | Construction | $86,400 | $87,014 | 7 | <$5M | AI Deep Dive |
| Grader Mike LLC | Construction | $86,400 | $87,329 | 8 | $9.1M | AI Deep Dive |
| Key West Urgent Care, Inc. | Health Care and Social Assistance | $86,348 | $86,667 | 9 | <$5M | AI Deep Dive |
| Key West Urgent Care, Inc. | Health Care and Social Assistance | $86,347 | $87,151 | 8 | <$5M | AI Deep Dive |
| Michael Mcivor M.d, P.a. | Health Care and Social Assistance | $85,800 | $0 | 8 | <$5M | AI Deep Dive |