Pepe's Eldest Café in Key West is very pet friendly and has even been known to put together their own pet calendar in the past. When you visit, you'll see their fence where not only people can peer into the patio/dining area but there are also ‘eye holes' for cats and dogs! Not to mention their food is awesome for breakfast, lunch and dinner... including fresh squeezed cocktails... yum!
Hurricane Hole Marina and Bar & Grill on Stock Island in Key West opens at 11 each day for lunch and dinner right on the water. Plus, watch their charterboats come in with their daily catch... talk about fresh! Leashed pets are always welcome at the Hole and you might want to introduce your pet to the Lazy Dog folks who rent out paddleboards, kayaks, and boats.
Snook's Bayside in Key Largo has a beautiful restaurant and grand tiki bar that welcomes pets too. Their food is fresh and delicious, cocktails are refreshing and the sunset over the Bay is breathtaking.
The Hogfish Bar & Grill is a place where you can relive old Key West. Pets are welcome and you can rub elbows with some of the shrimpers and liveaboards in the marina next door. The fish tacos are some of the best in the Keys (according to this writer who's always in search of a good fish taco!!).
The Cracked Conch Café in Marathon also has an outdoor patio where pets are welcome. They're open for breakfast, lunch and dinner and, of course, feature conch specialties like conch eggs benedict, conch picatta and more as well as a full bar.
The Island Grill has two locations in the Upper Keys. One is right on the beach in Key Largo (Oceanside) while the other is next to the drawbridge in Islamorada. They both welcome the puppies and when you're there you MUST try their delicious and unique Tuna nachos.
Schooner Wharf bar is so pet friendly that their saying is "Hang with the Big Dogs" You might want to grab one of those keepsake t-shirts. They offer breakfast, lunch and dinner and entertainment daily with generous cocktails.
Geiger Key Fish Camp restaurant and tiki bar is located within an RV park. It's a little hard to find just off of Big Coppitt Key in the Lower Keys. It's funky, laid back and the food is great. Plus, you can rent a kayak and go exploring with your doggy after your meal if you want!
Finally, if you just want your pooch to get some exercise, here are the beaches you can visit with no problem: Dog Beach (next to Louie's Backyard in Key West), Boca Chica Beach (just past Geiger Key) next to the Naval air station, Coco Plum Beach in Marathon and Ann's Beach in Islamorada right on US 1.
So treat yourself and your pet to a vacation in the Keys and give the dog a bone!