| Key West Surgical Group INC | Health Care and Social Assistance | $395,400 | $399,585 | 12 | <$5M |  AI Deep Dive |
| Casa Cayo Hueso LLC | Accommodation and Food Services | $390,500 | $396,455 | 44 | $7.8M | AI Deep Dive |
| Mckendry Builders Inc. | Construction | $387,800 | $389,998 | 15 | <$5M | AI Deep Dive |
| Mckendry Builders INC | Construction | $387,800 | $391,883 | 15 | <$5M | AI Deep Dive |
| Two Friends Patio Restaurant LLC | Accommodation and Food Services | $382,500 | $386,676 | 34 | $6.0M | AI Deep Dive |
| Boyd's Key West Campground Inc. | Accommodation and Food Services | $381,362 | $383,745 | 30 | $9.4M | AI Deep Dive |
| 1000 Atlantic Boulevard, LLC | Accommodation and Food Services | $381,150 | $387,757 | 50 | $8.9M | AI Deep Dive |
| S.o.a.p. Del Dia INC | Accommodation and Food Services | $377,483 | $381,101 | 45 | $8.0M | AI Deep Dive |
| Onpointe Restaurant Group LLC | Accommodation and Food Services | $376,316 | $378,521 | 41 | $7.3M | AI Deep Dive |
| The Basilica School of Saint Mary Star of the Sea | Educational Services | $375,000 | $378,958 | 47 | N/A | AI Deep Dive |
| Mad Eats Key West LLC | Accommodation and Food Services | $373,994 | $377,160 | 41 | $7.3M | AI Deep Dive |
| Hogs Breath Saloon of Key West INC | Accommodation and Food Services | $368,698 | $370,910 | 43 | $7.6M | AI Deep Dive |
| Strunk Ace Hardware, Inc. | Retail Trade | $364,400 | $366,758 | 28 | $5.8M | AI Deep Dive |
| Monroe Concrete Products, Inc. | Manufacturing | $358,700 | $360,832 | 23 | $22.8M | AI Deep Dive |
| Southernmost House Ltd | Accommodation and Food Services | $348,999 | $352,605 | 44 | $13.8M | AI Deep Dive |
| Denny's Restaurant | Accommodation and Food Services | $338,251 | $340,641 | 30 | $5.3M | AI Deep Dive |
| Salvage Management Company INC | Transportation and Warehousing | $333,209 | $336,088 | 27 | <$5M | AI Deep Dive |
| Pepe's Cafe Inc. | Accommodation and Food Services | $331,700 | $334,538 | 44 | $7.8M | AI Deep Dive |
| Lucy's Duval LLC | Accommodation and Food Services | $328,878 | $332,779 | 267 | $47.4M | AI Deep Dive |
| Smith Hawks Pl | Professional, Scientific, and Technical Services | $327,892 | $273,900 | 17 | <$5M | AI Deep Dive |
| Island Hotel Properties Inc. | Accommodation and Food Services | $324,443 | $326,300 | 35 | $10.9M | AI Deep Dive |
| Sub Zero INC | Construction | $322,800 | $322,045 | 22 | $7.0M | AI Deep Dive |
| Sub Zero INC | Construction | $318,064 | $319,858 | 22 | $7.0M | AI Deep Dive |
| Front Street Enterprises, LLC | Accommodation and Food Services | $313,800 | $317,827 | 58 | $10.3M | AI Deep Dive |
| Last Key Realty INC | Real Estate and Rental and Leasing | $313,315 | $317,406 | 19 | <$5M | AI Deep Dive |