| Mangoes Restaurant LLC | Accommodation and Food Services | $255,269 | $257,545 | 17 | <$5M |  AI Deep Dive |
| Conch Flyer Concessions LLC | Accommodation and Food Services | $253,400 | $256,553 | 23 | <$5M | AI Deep Dive |
| Sarah Luna INC | Accommodation and Food Services | $251,400 | $254,263 | 25 | <$5M | AI Deep Dive |
| Pbp Marina INC | Accommodation and Food Services | $250,922 | $253,647 | 48 | $5.9M | AI Deep Dive |
| Swimline Pool Products | Retail Trade | $250,000 | $20,055 | 2 | <$5M | AI Deep Dive |
| Horay Restaurant Group LLC | Accommodation and Food Services | $247,642 | $249,520 | 91 | $16.2M | AI Deep Dive |
| Kw Resort Utilities Corp | Real Estate and Rental and Leasing | $247,245 | $249,470 | 13 | <$5M | AI Deep Dive |
| Neuroscience Associates INC | Health Care and Social Assistance | $245,800 | $248,736 | 16 | <$5M | AI Deep Dive |
| Sjkwd, LLC | Accommodation and Food Services | $241,608 | $244,553 | 40 | $7.1M | AI Deep Dive |
| Inter-Ocean Holdings LLC | Accommodation and Food Services | $241,100 | $243,417 | 21 | $6.6M | AI Deep Dive |
| Surgery Center of Key West LLC | Health Care and Social Assistance | $240,500 | $243,259 | 16 | $5.0M | AI Deep Dive |
| Sq1 of Key West LLC | Accommodation and Food Services | $238,000 | $239,754 | 21 | <$5M | AI Deep Dive |
| Conch Cafe INC | Accommodation and Food Services | $233,422 | $236,191 | 15 | <$5M | AI Deep Dive |
| Key West Butterfly & Nature Co | Arts, Entertainment, and Recreation | $233,100 | $236,292 | 35 | $5.3M | AI Deep Dive |
| Wings of Imagination INC | Retail Trade | $233,100 | $234,505 | 35 | $5.5M | AI Deep Dive |
| Island Hotel Properties, Inc. | Accommodation and Food Services | $231,745 | $234,519 | 33 | $10.3M | AI Deep Dive |
| Wellings Automotive LLC | Wholesale Trade | $230,384 | $231,741 | 21 | $6.4M | AI Deep Dive |
| Nearshore Electric INC | Construction | $226,800 | $229,767 | 17 | $5.6M | AI Deep Dive |
| Baronald Corporation | Accommodation and Food Services | $223,200 | $226,508 | 28 | $8.8M | AI Deep Dive |
| Longstock Ii, LLC | Arts, Entertainment, and Recreation | $222,400 | $224,849 | 23 | <$5M | AI Deep Dive |
| Gary the Carpenter Construction Inc. | Construction | $220,535 | $224,113 | 30 | $9.5M | AI Deep Dive |
| Gary the Carpenter Construction, Inc. | Construction | $220,535 | $223,592 | 30 | $34.2M | AI Deep Dive |
| Marino Construction Group, Inc. | Construction | $217,198 | $219,985 | 18 | $5.5M | AI Deep Dive |
| May Sands Montessori School | Educational Services | $215,900 | $218,125 | 26 | N/A | AI Deep Dive |
| Redfish Bluefish INC | Accommodation and Food Services | $212,481 | $215,674 | 21 | <$5M | AI Deep Dive |