Experience the First Gulf Front Restaurant in Madeira Beach – Caddy’s

When you’re taking a beach vacation, chances are that you want to stay near the water as long as possible. After all, for most people, a trip to the beach is something that doesn’t happen every day! You can enjoy swimming, playing beach volleyball near the waves, or maybe casting your line to try to reel in tonight’s dinner.

But on the beach, you’re not restricted to just the sand. Perhaps you want to visit one of the mouthwatering Madeira Beach waterfront restaurants, and eat delicious local food while getting a great view of the Gulf.

While staying in one of our Madeira Beach rentals, be sure to experience a part of history at Caddy’s, the first Gulf-front restaurant in town! 

friends eating at a Madeira Beach restaurant
Photo from Shutterstock


With locations all around the area, Caddy’s is nothing short of a local staple. Their Madeira Beach location, though, truly stands out from the rest. This establishment is unique in that it’s the first Gulf-front restaurant to pop up on the shores of Madeira Beach! You’ll be within walking distance of the beach when you’re done with your meal, meaning you can soak up as much sunshine as you please. 

At Caddy’s, you can rest assured that your experience will be nothing short of spectacular. Every guest is greeted at the door with a smile before being led to a table with a fantastic view of the water and the unique décor throughout the restaurant. You can expect all kinds of great company, delicious menu offerings for everyone in the family (and at budget-friendly prices), and a laid-back atmosphere any time of the day. 

The Menu

When you come in for breakfast, you know you’re getting the day started off right. Select something hearty like the Classic Breakfast, Caddy’s Famous Biscuits and Gravy, or the Traditional Oatmeal. If you’re looking for something a bit more unique, try the Son of a Beach Burrito or the Corned Beef Hash and Eggs. Take it one step further by enjoying bottomless mimosas until 11 a.m. or other adult breakfast drinks like the Gulf of Mexico Coffee, Fuzzy Bellini, Tequila Sunrise, or Bloody Maria. 

If you’re visiting for lunch or dinner, there’s even more to choose from. Start your meal with an appetizer such as the Sesame Crusted Ahi Tuna, Grouper Nuggets, or Trio Dip. When it comes to your main course, check out the selection of handhelds, featuring delicious options like the Bacon BBQ Burger and Crab Cake BLT. Or, consider house specialties like the Coconut Shrimp Basket, Fish and Chips, or Caddy’s Seafood Platter. Finish it off with a slice of Key Lime Pie or the Chocolate Tidal Wave! 

Caddy’s also ensures you’re taken care of in terms of your thirst. There is a vast drink menu to offer something for every palate. You can enjoy cocktails like the Rocky Margarita, Spiked Strawberry Lemonade, or Mai Tai. There are also unique options you can’t get anywhere else, including the Dragon Berry Mojito, Caddy’s Gulf Cooler, Beachside Jack, or Loosey Goosey. Not in the mood for a cocktail? Check out the beer and seltzer list or get some wine on tap, by the glass, or by the bottle.  


In addition to the everyday favorites on the menu, you can also visit Caddy’s for various specials throughout the week. First, we’ve got to mention Happy Hour. Every Monday through Friday from 3 to 6 p.m., enjoy $4 wells, $5 house wine, and $5 select cocktails. You can save some cash and get a great waterfront meal with the family! 

If you’re looking for a killer breakfast, come into Caddy’s any day between 8 and 11 a.m. Not only can you enjoy some amazing food to get your day started off on the right foot, but you can also treat yourself to bottomless mimosas right on the beach! Get a picnic table right on the sand for the ultimate start to your morning.

Finally, consider coming out to Caddy’s Sunset Sessions every night from 3 to 7 p.m. During this time, you can enjoy your meal while you jam to the musical stylings of some of the area’s most talented up-and-coming artists. Lately, guests have loved listening to acts like Eric Engle, Crownz, Nathan Allen, Matt Bellina, and others. Check out Caddy’s website for a full event calendar.

Hours and Directions

Guests are welcome to visit Caddy’s on Monday through Thursday from 11 a.m. to 10 p.m. You can also visit on Friday from 11 a.m. to 11 p.m., Saturday from 8 a.m. to 11 p.m., or Sunday from 8 a.m. to 10 p.m.

In order for you to experience one of the best restaurants in Madeira Beach, FL, you’re going to have to know how to get there! Luckily, Caddy’s is just a short drive away from our St. Pete Beach rentals. Simply drive northbound on Blind Pass Road and continue north as the road changes into FL-699 N/Gulf Boulevard. You’ll travel for 3.6 miles (you’ll know you’re on the right track when you pass by Waffle House after about a mile and a half). Then, you’ll see Caddy’s on your left! All in all, the journey only takes about 10 minutes. 

Where to Stay

When it comes to the best Madeira Beach restaurants, Caddy’s is a spectacular option that shouldn’t be left off of your itinerary. But of course, visiting Caddy’s is just one of the incredible things to do in Madeira Beach! You can head into town to check out a local museum or pick up a unique souvenir to remember your travels, or you can return to one of our Madeira Beach rentals to relax and unwind with the ones you love most. 

Travel Resort Services is proud to offer a huge catalog of rental properties throughout the Madeira Beach area, guaranteeing that every single group can find a rental to suit their needs. We, of course, offer rentals in Madeira Beach itself, but you can also opt to stay in one of our St. Pete Beach rentals or one of our properties in Redington Beach. Select from smaller one- or two-bedroom rentals for couples or families, or if you need something a bit bigger, get three or four bedrooms!

Book Your Stay

Caddy’s is a classic around Madeira Beach, just like our Madeira Beach vacation rentals! Take a look at our inventory and book your dates today!

Regardless of which property you choose, you’ll have a whole host of amenities to enjoy. Prepare meals in your fully stocked kitchen, enjoy the view from your balcony or patio, watch a movie on your flat-screen TV, or get some R&R in your spacious bedrooms. You’ll also enjoy being just moments away from all the area’s best attractions, from beaches to seafood restaurants to nature parks and more. 

On top of all that, you’ve got the support of our passionate team to make sure your vacation is the best it can be. Whether you have a question about your rental or want to know about things to do around town, our team can help you out. We’re never more than a phone call away if you need us. So, browse our selection of Madeira Beach rentals and book your trip today!