Winter Park, Park Avenue shops (near Orlando). Almost all stores allow pets inside, including Williams Sonoma, Restoration Hardware, etc. Storehouse Furniture even has a goodie bar inside with treats for humans and pets. Outdoor cafe dining with pets options are also available. And, for the humans, don't miss Peterbrooke Chocolates.
Park Avenue in Winter Park, FL is an entire pet-friendly street. All of the merchants and most of the restaurants welcome pets (some even have pet menus!). This upscale neighborhood shopping area is located in beautiful downtown Winter Park, FL.