| The Mel Fisher Maritime Heritage Society INC | Arts, Entertainment, and Recreation | $175,270 | $178,104 | 12 | N/A |  AI Deep Dive |
| Kw Five II LLC | Accommodation and Food Services | $175,000 | $175,788 | 20 | <$5M | AI Deep Dive |
| Chico's Cantina of Key West INC | Accommodation and Food Services | $175,000 | $177,542 | 36 | $6.4M | AI Deep Dive |
| Arnold's Auto and Marine Repair, INC | Other Services (except Public Administration) | $174,600 | $175,924 | 12 | <$5M | AI Deep Dive |
| Southernmost House Ltd | Accommodation and Food Services | $174,225 | $176,529 | 20 | $6.3M | AI Deep Dive |
| Lines Unlimited INC | Other Services (except Public Administration) | $173,020 | $174,447 | 18 | <$5M | AI Deep Dive |
| Southernmost Sandbar Corp | Accommodation and Food Services | $173,000 | $175,687 | 26 | $8.1M | AI Deep Dive |
| Florida Keys Spca | Other Services (except Public Administration) | $171,871 | $173,790 | 24 | N/A | AI Deep Dive |
| Antonia's Kw LLC | Accommodation and Food Services | $171,206 | $172,595 | 9 | <$5M | AI Deep Dive |
| Barnes Alarm Systems Inc. | Administrative and Support and Waste Management | $170,000 | $171,355 | 15 | <$5M | AI Deep Dive |
| Zaraab LLC | Accommodation and Food Services | $169,889 | $172,065 | 31 | $5.5M | AI Deep Dive |
| Fish Dance Inc. | Accommodation and Food Services | $168,147 | $169,700 | 7 | <$5M | AI Deep Dive |
| Conch Cafe INC | Accommodation and Food Services | $166,729 | $169,040 | 20 | <$5M | AI Deep Dive |
| The Gardens Hotel LLC | Accommodation and Food Services | $165,908 | $168,222 | 18 | $5.6M | AI Deep Dive |
| Old Tow Mexican Cafe INC | Accommodation and Food Services | $164,830 | $166,085 | 12 | <$5M | AI Deep Dive |
| Cayo Hueso Company | Accommodation and Food Services | $164,700 | $165,693 | 15 | <$5M | AI Deep Dive |
| Tejas LLC | Accommodation and Food Services | $164,400 | $165,071 | 8 | <$5M | AI Deep Dive |
| Chicos Cantina of Key West INC | Agriculture, Forestry, Fishing and Hunting | $161,300 | $163,191 | 20 | <$5M | AI Deep Dive |
| Key West Golf Club, LLC | Real Estate and Rental and Leasing | $160,414 | $161,871 | 35 | $5.3M | AI Deep Dive |
| Lines Unlimited Inc. | Construction | $160,043 | $160,723 | 18 | $6.7M | AI Deep Dive |
| Hector Guzman, Dds, P.a. | Health Care and Social Assistance | $159,504 | $161,461 | 12 | <$5M | AI Deep Dive |
| Montessori Children's School of Key West Inc. | Educational Services | $158,876 | $159,927 | 12 | N/A | AI Deep Dive |
| Piazzolacrema LLC | Accommodation and Food Services | $157,220 | $158,980 | 20 | <$5M | AI Deep Dive |
| Four Star Rentals INC | Real Estate and Rental and Leasing | $156,940 | $157,864 | 14 | $6.3M | AI Deep Dive |
| Pasta Garden INC | Accommodation and Food Services | $155,750 | $156,719 | 16 | <$5M | AI Deep Dive |