| R & B Hair Shop | Anstruther | Hairdressers | |
| R & B Hair Shop | Pittenweem | Hairdressers | |
| Racket Restringing | St Monans | Sports | |
| Railway Inn The | Lower Largo | Public Houses | |
| Rainbow | Upper Largo | Painter / Decorator | |
| Rainbow Crafts | Anstruther | Art & Craft | |
| Reekie Fish Merchant | Pittenweem | Fish-mongers | |
| Reflexology Clinic | St Monans | Health & Beauty | |
| Rennie Gordon | St Monans | Farms | |
| Reynolds Properties | Anstruther | Builder | |
| Richardson's of Crail | Crail | Garages | |
| Robertson David I. | Crail | Farms | |
| Rodger Alex | Anstruther | Architects | |
| Royal Bank of Scotland | Anstruther | Bank | |
| Rutherfords | Elie | Delicatessen |