| La Siesta Seas LLC | Accommodation and Food Services | $956,536 | $962,930 | 94 | $16.7M |  Research |
| La Siesta Seas LLC | Accommodation and Food Services | $693,240 | $687,693 | 94 | $29.4M | Research |
| Lazy Days Restaurant LLC | Accommodation and Food Services | $656,083 | $661,583 | 81 | $14.4M | Research |
| Theater of the Sea Inc. | Arts, Entertainment, and Recreation | $595,165 | $601,844 | 75 | $10.5M | Research |
| Theater of the Sea Inc. | Arts, Entertainment, and Recreation | $513,287 | $516,780 | 64 | $9.0M | Research |
| Flamingo Air of Florida Keys INC | Accommodation and Food Services | $496,100 | $501,240 | 60 | $10.7M | Research |
| Witness Resources Inc. | Accommodation and Food Services | $468,726 | $475,627 | 29 | $9.1M | Research |
| R Brown Holdings LLC | Accommodation and Food Services | $377,851 | $381,944 | 62 | $11.0M | Research |
| Markeywest Real Holdings INC | Accommodation and Food Services | $359,321 | $363,032 | 56 | $9.9M | Research |
| Montessori Island Charter School INC | Educational Services | $350,450 | $351,650 | 27 | N/A | Research |
| Equine Luxury Properties LLC | Real Estate and Rental and Leasing | $343,227 | $345,832 | 18 | <$5M | Research |
| Witness Resources, Inc. | Accommodation and Food Services | $340,100 | $342,755 | 28 | $8.8M | Research |
| Shrimp Improvement Systems LLC | Agriculture, Forestry, Fishing and Hunting | $317,550 | $319,843 | 52 | $8.5M | Research |
| Green Turtle LLC | Accommodation and Food Services | $305,422 | $306,652 | 44 | $7.8M | Research |
| Montessori Island Charter School | Educational Services | $285,458 | $286,980 | 26 | N/A | Research |
| R Brown Holdings | Accommodation and Food Services | $273,000 | $275,738 | 39 | $6.9M | Research |
| Markeywest Real Holdings, Inc. | Management of Companies and Enterprises | $256,774 | $259,862 | 50 | $8.2M | Research |
| Lindholm Construction INC | Construction | $254,000 | $256,681 | 57 | $18.8M | Research |
| Lindholm Construction INC | Construction | $254,000 | $256,223 | 39 | $12.9M | Research |
| The Hungry Heron of the Keys LLC | Accommodation and Food Services | $231,340 | $233,982 | 28 | <$5M | Research |
| Rex Houston Air Conditioning & Refrigeration, Inc. | Construction | $212,855 | $215,740 | 15 | <$5M | Research |
| Islamorada Leisure Properties INC | Accommodation and Food Services | $198,602 | $200,055 | 13 | <$5M | Research |
| Islamorada Shrimp Shack LLC | Accommodation and Food Services | $190,478 | $191,467 | 52 | $9.2M | Research |
| Vernis & Bowling of the Florida Keys PA | Professional, Scientific, and Technical Services | $181,306 | $182,633 | 16 | <$5M | Research |
| Windy Day Plumbing Company, Inc. | Construction | $180,655 | $183,420 | 11 | <$5M | Research |