16 Best Dive Bars near Winter Park

“Great dive bar atmosphere with fresh as it gets oysters! The bartender grabs your beer, wine, soda or whatever, takes your order AND shucks your oysters! The night I was there they had Chesapeake Bay oysters. We got them raw and they were magnificent! Napkin caddies mounted right above the bar seats. Super convenient and great use of space. Super smart on many levels, if you ask me! We got a pound of peek and eat shrimp, BIG and perfectly seasoned! So delicious! Last we had to try the gumbalya and it did not disappoint. Full of shrimp, andouille sausage etc (I can’t recall all that’s in it). Broth is full of flavor with a pretty good kick! Not a lot of rice, contradictory to the name, but I wouldn’t change a thing. This is definitely worth the visit! Very reasonably priced, too 👍🏼👍🏼“

“I love this bar but Saturday night I paid my tab for 109.00 woke up Sunday and the charge was 170.00 on my card waiting for them to open because I need answers and my money back....“

“Great food, great atmosphere“

“Casey’s on Central is hands down one of the best spots in downtown Orlando! The vibe is always great, the drinks are strong, and the music keeps the energy going all night. Every single bartender here is top-tier — they’re fast, friendly, and always make you feel welcome. You can tell they genuinely care about giving everyone a good time. Whether you’re starting your night or ending it, Casey’s is always the move!“

“I had been looking around for a good punk bar and Will’s Pub had incredible vibes. The bands at the Underground fest were so nice, the atmosphere was fantastic, and the drinks were great! The bartenders were chill and there was plenty of room to move around and watch the other bands perform in the different areas. This will definitely be my new favorite hangout spot!“

“I have been coming here for years and have always had a great time. With the new addition of Cassandra, the staff and management are just off the charts down to earth and fast. Great giant dive bar pool spot and the food ain't bad either.“

“awesome people,friendly atmosphere, and as cheers would say, A place where everyone knows your name..lol“

“We wanted to go somewhere we don't normally go, off the beaten path, just to have a day with friends to hang out and relax outside of our normal routine. The Caboose did not disappoint.Everything was amazing. We ordered a few rounds of drinks, shots, and food. Mozzarella sticks, flatbread pizza, nachos etc,. The food came out promptly and was spot-on. Our bartender Mari was attentive and offered great customer service, even when the POS system went down at peak business she worked through it and still managed to take care of everyone. We spent around $135 and she had no problem splitting the tab as requested. Great experience all-around. Highly recommended.

Vegetarian options: They do have vegetarian options on the menu, including the vegan black and blue flatbread pizza, which is mushrooms, onions, tomatoes, mozzarella, and blue cheese.“

“I have been a Hideaway fan for years! I was so happy to see that they were able to move across the street (from construction, that forced them out) but continued with the same great local friendly atmosphere 💕
Our doodles love the dog menu“

“First time in here was sitting at the bar and the bartender came within 30 seconds of asking me what I would like. Very elegant place even though it’s a hole in the wall it’s very nice if you come down to Florida, you have to visit this place.“

“Was a fun dingy place to play. Perfect for a punk show although a very tight squeeze. I'm not sure what food was offered, but basic variety of beers that you cannot go wrong with.

Vegetarian options: Idk.

Dietary restrictions: Idk

Parking: All up and down the avenue. The parking is spread out pretty well!

Kid-friendliness: Don't think you're going to get kids inside LOL.

Wheelchair accessibility: The entire space is one room so you will definitely be fine wheeling in.“

“Always Great place good food and drinks“

“My first visit and I found a very welcoming crowd. Everyone was polite and respectful of others. Drinks were strong af just like I like. Pet friendly and many TVs for your sports watching pleasure. The food is supplied by 3rd party businesses ,no food prepared by bar.“

“Awesome place. Best place in town.“

“Good place to hang. Drink. Play pinball. Play pool. Socialize.“

“Dara and Pauline was amazing if it wasn’t for them I doubt I would give this place 5 stars they really made my experience amazing and I never go out! I’m so thankful for them. They really elevated this place !!!! I actually will come back just to see them and enjoy the night at the bar with them! Best place if they working!!!“