| May Sands Montessori School | Educational Services | $211,800 | $213,936 | 26 | N/A |  AI Deep Dive |
| La Te Da | Accommodation and Food Services | $211,472 | $213,865 | 38 | $6.7M | AI Deep Dive |
| Moondog Cafe LLC | Accommodation and Food Services | $211,218 | $213,209 | 20 | <$5M | AI Deep Dive |
| Mama's Rock and Sand INC | Administrative and Support and Waste Management | $210,412 | $212,873 | 23 | <$5M | AI Deep Dive |
| Mama's Rock and Sand, INC | Administrative and Support and Waste Management | $210,400 | $212,416 | 30 | $6.5M | AI Deep Dive |
| A Plus Roofing of Key West, INC | Construction | $209,700 | $210,888 | 29 | $9.6M | AI Deep Dive |
| One Call Construction INC | Construction | $209,289 | $211,703 | 8 | <$5M | AI Deep Dive |
| Pinnacle Aba Services Inc. | Health Care and Social Assistance | $208,743 | $209,954 | 18 | <$5M | AI Deep Dive |
| Pinnacle Aba Services, Inc. | Health Care and Social Assistance | $208,700 | $210,741 | 19 | <$5M | AI Deep Dive |
| Paradise Inn Hotel LLC | Accommodation and Food Services | $202,652 | $204,498 | 10 | <$5M | AI Deep Dive |
| Barnes Alarm Systems INC | Administrative and Support and Waste Management | $202,100 | $203,812 | 15 | <$5M | AI Deep Dive |
| Key West Art and Historic Society | Arts, Entertainment, and Recreation | $200,300 | $201,941 | 30 | N/A | AI Deep Dive |
| Smokin Tuna LLC | Accommodation and Food Services | $200,200 | $201,524 | 24 | <$5M | AI Deep Dive |
| Habibi Corporation | Accommodation and Food Services | $198,510 | $280,431 | 35 | <$5M | AI Deep Dive |
| Habibi Corporation | Accommodation and Food Services | $198,510 | $201,526 | 38 | <$5M | AI Deep Dive |
| Kosmic of Key West INC | Arts, Entertainment, and Recreation | $198,070 | $198,983 | 18 | <$5M | AI Deep Dive |
| Kosmic of Key West, Inc. | Accommodation and Food Services | $198,000 | $200,398 | 24 | <$5M | AI Deep Dive |
| Fat Tuesday/key West Limited Partnership | Accommodation and Food Services | $195,797 | $197,701 | 26 | <$5M | AI Deep Dive |
| Fishbusterz Retail, LLC | Agriculture, Forestry, Fishing and Hunting | $195,300 | $197,437 | 15 | <$5M | AI Deep Dive |
| Mayan Parrot LLC | Accommodation and Food Services | $194,967 | $196,370 | 40 | $7.1M | AI Deep Dive |
| Southernmost Sandbar Corp | Accommodation and Food Services | $193,767 | $196,305 | 24 | $7.5M | AI Deep Dive |
| Curry Mansion Corporation | Accommodation and Food Services | $192,997 | $194,428 | 15 | <$5M | AI Deep Dive |
| Lacrematipiazzo LLC | Accommodation and Food Services | $191,479 | $193,514 | 14 | <$5M | AI Deep Dive |
| Riesi Pizza, LLC | Accommodation and Food Services | $191,400 | $193,856 | 49 | $8.7M | AI Deep Dive |
| Roof Top Cafe, LLC | Accommodation and Food Services | $191,311 | $134,098 | 27 | <$5M | AI Deep Dive |