| 907 Whitehead St Corp | Arts, Entertainment, and Recreation | $312,500 | $315,252 | 38 | $5.8M |  AI Deep Dive |
| Hildenborough Hotels Limited, Inc. | Accommodation and Food Services | $310,077 | $312,617 | 26 | $8.1M | AI Deep Dive |
| Eaton Street Lumber LLC | Retail Trade | $309,900 | $312,913 | 20 | <$5M | AI Deep Dive |
| La Te Da Key West LLC | Accommodation and Food Services | $296,061 | $298,786 | 27 | <$5M | AI Deep Dive |
| Moondog Cafe LLC | Accommodation and Food Services | $295,706 | $297,115 | 23 | <$5M | AI Deep Dive |
| Imcmv Key West Cafe LLC | Accommodation and Food Services | $292,800 | $295,439 | 47 | $8.3M | AI Deep Dive |
| Kenmar General Contracting, L.l.c | Construction | $290,844 | $293,091 | 17 | $5.8M | AI Deep Dive |
| Conch Flyer Concessions LLC | Accommodation and Food Services | $289,151 | $292,990 | 24 | <$5M | AI Deep Dive |
| Smith Hawks Pl | Real Estate and Rental and Leasing | $288,274 | $295,166 | 15 | <$5M | AI Deep Dive |
| Marino Construction Group INC | Construction | $287,502 | $291,086 | 24 | $27.3M | AI Deep Dive |
| Hog's Breath Saloon of Key West, LLC | Accommodation and Food Services | $284,600 | $287,043 | 33 | $5.9M | AI Deep Dive |
| Lucy's Duval LLC | Accommodation and Food Services | $273,800 | $168,766 | 35 | $6.2M | AI Deep Dive |
| A.h. of Monroe County, Inc. | Public Administration | $273,200 | $274,794 | 21 | N/A | AI Deep Dive |
| Mayan Parrot LLC | Accommodation and Food Services | $272,954 | $275,400 | 35 | <$5M | AI Deep Dive |
| Boyds Key West Campground INC | Accommodation and Food Services | $272,400 | $273,876 | 32 | $10.0M | AI Deep Dive |
| Baronald Corporation | Accommodation and Food Services | $271,100 | $274,572 | 23 | $7.2M | AI Deep Dive |
| Onpointe Restaurant Group LLC | Accommodation and Food Services | $269,797 | $273,544 | 77 | $13.7M | AI Deep Dive |
| Certified Lower Keys Plumbing Inc. | Construction | $268,714 | $271,289 | 20 | $6.3M | AI Deep Dive |
| Riesi Pizza LLC | Accommodation and Food Services | $267,900 | $270,646 | 49 | $8.7M | AI Deep Dive |
| Kenmar General Contracting LLC | Construction | $263,585 | $265,650 | 17 | $19.4M | AI Deep Dive |
| Blue Native of the Florida Keys INC | Administrative and Support and Waste Management | $261,500 | $263,447 | 39 | $8.4M | AI Deep Dive |
| Cataract & Laser Center Partners LLC | Health Care and Social Assistance | $260,400 | $263,669 | 24 | <$5M | AI Deep Dive |
| A Plus Roofing of Key West INC | Construction | $257,500 | $258,602 | 15 | <$5M | AI Deep Dive |
| Keys Productions INC | Accommodation and Food Services | $257,500 | $260,404 | 47 | $5.8M | AI Deep Dive |
| Inter-Ocean Holdings LLC DBA Marquesa Hotel | Accommodation and Food Services | $257,273 | $258,431 | 20 | $6.3M | AI Deep Dive |