| Spottswood Management INC | Accommodation and Food Services | $2,473,000 | $2,520,605 | 322 | $100.7M |  Research |
| Spottswood Management INC | Accommodation and Food Services | $2,000,000 | $2,028,833 | 241 | $75.4M | Research |
| The College of the Florida Keys | Educational Services | $1,742,208 | $1,757,483 | 331 | N/A | Research |
| Hayes Robertson Group INC | Accommodation and Food Services | $1,718,650 | $1,744,764 | 131 | $23.3M | Research |
| P&g Power Co | Construction | $1,607,485 | $1,614,183 | 60 | $18.6M | Research |
| Charley Toppino & Sons INC | Construction | $1,587,823 | $1,548,770 | 116 | $43.5M | Research |
| Charley Toppino & Sons INC | Construction | $1,555,000 | $1,565,669 | 152 | $47.1M | Research |
| Csi Dmc INC | Other Services (except Public Administration) | $1,385,360 | $1,402,022 | 55 | $10.5M | Research |
| Sloppy Joe's Enterprises INC | Accommodation and Food Services | $1,299,700 | $1,314,466 | 110 | $13.5M | Research |
| Historic Tours of America, Inc. | Administrative and Support and Waste Management | $1,292,250 | $1,309,588 | 99 | $31.3M | Research |
| Historic Tours of America INC | Transportation and Warehousing | $1,292,200 | $0 | 85 | $21.6M | Research |
| Fury Management, INC | Arts, Entertainment, and Recreation | $1,291,629 | $1,302,931 | 148 | $20.7M | Research |
| Fury Management INC | Arts, Entertainment, and Recreation | $1,291,629 | $1,310,286 | 144 | $20.2M | Research |
| Hayes Robertson Group INC | Real Estate and Rental and Leasing | $1,227,608 | $1,251,103 | 131 | $15.3M | Research |
| Old Town Trolley Tours of Washington INC | Administrative and Support and Waste Management | $1,205,429 | $1,222,941 | 138 | $43.6M | Research |
| Tropical Shell & Gift INC | Administrative and Support and Waste Management | $1,089,750 | $1,104,371 | 143 | $45.2M | Research |
| Tropical Shell & Gift INC | Retail Trade | $1,089,700 | $0 | 72 | $15.6M | Research |
| Conch Tour Train INC | Administrative and Support and Waste Management | $1,020,500 | $1,043,688 | 107 | $33.8M | Research |
| Conch Tour Train INC | Transportation and Warehousing | $1,020,500 | $0 | 55 | $13.9M | Research |
| Dion Enterprises LLC | Retail Trade | $972,527 | $978,335 | 128 | $32.0M | Research |
| Noble House Ocean Key LLC | Accommodation and Food Services | $967,000 | $972,372 | 117 | $36.6M | Research |
| S D R & R Corporation | Accommodation and Food Services | $952,445 | $968,372 | 100 | $17.8M | Research |
| Sloppy Joe's Enterprises, INC | Accommodation and Food Services | $928,300 | $857,765 | 110 | $13.5M | Research |
| Pelagic Marina Investments LLC | Accommodation and Food Services | $909,640 | $917,069 | 106 | $18.8M | Research |
| Wesley House Family Services | Health Care and Social Assistance | $851,576 | $859,018 | 72 | N/A | Research |