Markum Park in Weston, FL, has a lovely dog park that they named Barkham Park (get it?). There's a side for large pets and for small pets as well. It has lots of space for pets to run and jump and it even has 2 mini obstacle courses. The atmosphere is always friendly and it has dog clean-up stations with bags and cold water fountains for humans and dogs alike.
Village Pub is agay-friendly sports bar, which has a two-for-one happy hour until 9 p.m. Monday to Saturday, allows well behaved dogs on their front and back patios until 6 p.m. daily. They offer doggie biscuits, too.
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.