| Csi Dmc INC | Other Services (except Public Administration) | $804,900 | $816,213 | 55 | $10.5M |  AI Deep Dive |
| Sigsbee Charter School, Inc. | Educational Services | $798,321 | $802,936 | 73 | N/A | AI Deep Dive |
| On-Pointe Entertainment Group L.l.c. | Accommodation and Food Services | $796,668 | $800,983 | 89 | $15.8M | AI Deep Dive |
| Bella Construction of Key West Inc. | Construction | $783,524 | $789,213 | 121 | $37.5M | AI Deep Dive |
| Bella Construction of Key West, Inc. | Construction | $783,523 | $794,666 | 65 | $74.1M | AI Deep Dive |
| Moro Management, INC | Accommodation and Food Services | $770,000 | $776,919 | 52 | $6.4M | AI Deep Dive |
| Pelagic Marina Investments LLC | Accommodation and Food Services | $728,400 | $735,482 | 65 | $11.5M | AI Deep Dive |
| Louie's Backyard INC | Accommodation and Food Services | $702,327 | $705,683 | 55 | $9.8M | AI Deep Dive |
| Simv Hotel 1, LLC | Accommodation and Food Services | $696,700 | $707,253 | 82 | $25.6M | AI Deep Dive |
| Key Honey Contracting LLC | Construction | $644,418 | $651,578 | 45 | $13.9M | AI Deep Dive |
| Two Friends Patio Restaurant LLC | Accommodation and Food Services | $617,200 | $622,635 | 107 | $19.0M | AI Deep Dive |
| Key West Seaport LLC | Accommodation and Food Services | $615,806 | $618,826 | 69 | $8.5M | AI Deep Dive |
| Sea Cups LLC | Accommodation and Food Services | $611,027 | $615,491 | 43 | $7.6M | AI Deep Dive |
| Florida Keys Electric INC | Construction | $595,908 | $600,062 | 50 | $16.5M | AI Deep Dive |
| On Pointe Entertainment Group LLC | Accommodation and Food Services | $590,400 | $598,502 | 60 | $7.3M | AI Deep Dive |
| Waterfront Brewery, LLC | Accommodation and Food Services | $582,032 | $590,892 | 65 | $11.5M | AI Deep Dive |
| Florida Straits Conch Company | Administrative and Support and Waste Management | $566,555 | $573,543 | 62 | $11.7M | AI Deep Dive |
| Louies Back Yard INC | Accommodation and Food Services | $561,800 | $566,544 | 60 | $10.7M | AI Deep Dive |
| Boat House Key West LLC | Accommodation and Food Services | $557,000 | $560,265 | 43 | $7.6M | AI Deep Dive |
| Moro Management, INC | Administrative and Support and Waste Management | $550,000 | $553,957 | 91 | $17.2M | AI Deep Dive |
| Casa Cayo Hueso LLC | Accommodation and Food Services | $546,700 | $555,948 | 44 | $7.8M | AI Deep Dive |
| Simv Hotel 1 LLC | Accommodation and Food Services | $543,339 | $536,744 | 51 | $15.9M | AI Deep Dive |
| S.o.a.p. Del Dia Inc. | Accommodation and Food Services | $528,477 | $533,527 | 43 | $7.6M | AI Deep Dive |
| Bruce L. Boros, M.d., P.a. | Health Care and Social Assistance | $516,394 | $520,143 | 80 | $25.1M | AI Deep Dive |
| Niles Sales and Service, Inc. | Retail Trade | $511,628 | $518,634 | 47 | $11.8M | AI Deep Dive |