| Niles Sales and Service Inc. | Retail Trade | $511,627 | $515,066 | 36 | $9.1M |  AI Deep Dive |
| Gemstone, LLC | Construction | $502,650 | $505,456 | 30 | $7.6M | AI Deep Dive |
| Buggy Bus Inc. | Administrative and Support and Waste Management | $501,000 | $507,819 | 54 | $17.1M | AI Deep Dive |
| Buggy Bus INC | Transportation and Warehousing | $501,000 | $0 | 27 | $6.8M | AI Deep Dive |
| Key Honey Contracting LLC | Construction | $497,400 | $501,932 | 47 | $15.0M | AI Deep Dive |
| Check Electric LLC | Construction | $462,070 | $466,203 | 59 | $19.4M | AI Deep Dive |
| Monroe Association for Retarded Citizens Inc. | Health Care and Social Assistance | $461,200 | $466,952 | 72 | N/A | AI Deep Dive |
| Monroe Association for Retarded Citizens, INC | Other Services (except Public Administration) | $461,200 | $464,800 | 72 | N/A | AI Deep Dive |
| Front Street Enterprises LLC | Accommodation and Food Services | $439,400 | $443,904 | 58 | $10.3M | AI Deep Dive |
| Sea Cups LLC | Accommodation and Food Services | $436,500 | $440,938 | 47 | $8.3M | AI Deep Dive |
| Faustos Food Palace LLC | Retail Trade | $434,600 | $438,246 | 64 | $16.0M | AI Deep Dive |
| Hildenborough Hotels Limited INC | Accommodation and Food Services | $434,109 | $437,665 | 23 | $7.2M | AI Deep Dive |
| Key West Seaport, LLC | Accommodation and Food Services | $424,437 | $427,437 | 75 | $13.3M | AI Deep Dive |
| Pepe's Cafe INC | Accommodation and Food Services | $417,600 | $419,862 | 41 | $7.3M | AI Deep Dive |
| Waterfront Brewery, LLC | Accommodation and Food Services | $415,737 | $425,565 | 65 | $11.5M | AI Deep Dive |
| Blue Native of the Florida Keys Inc. | Administrative and Support and Waste Management | $412,018 | $415,360 | 39 | $8.4M | AI Deep Dive |
| 907 Whitehead Street Corp | Arts, Entertainment, and Recreation | $411,900 | $417,655 | 26 | <$5M | AI Deep Dive |
| Last Key Realty INC | Real Estate and Rental and Leasing | $409,700 | $412,602 | 19 | <$5M | AI Deep Dive |
| Key West Orthopedics PA | Health Care and Social Assistance | $408,200 | $412,520 | 15 | <$5M | AI Deep Dive |
| Key West Orthopedics PA | Health Care and Social Assistance | $408,000 | $410,981 | 15 | <$5M | AI Deep Dive |
| Gary's Plumbing and Fire Inc. | Public Administration | $403,300 | $409,193 | 34 | N/A | AI Deep Dive |
| Gary's Plumbing and Fire INC | Construction | $403,300 | $408,487 | 33 | $10.4M | AI Deep Dive |
| Check Electric LLC | Construction | $402,200 | $405,507 | 59 | $19.4M | AI Deep Dive |
| Boat House Key West, LLC | Accommodation and Food Services | $397,800 | $231,145 | 43 | $7.6M | AI Deep Dive |
| Murphy's Law Pizza, LLC | Accommodation and Food Services | $396,615 | $401,716 | 75 | $13.3M | AI Deep Dive |