16 Best Dive Bars near Winter Park

1 Thirsty Gator

4.6 Superb 240 Reviews

3040 North Goldenrod Road, Winter Park

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“This was a spur of the moment stop. Definitely did not disappoint! Lisa and Tim were great. Fantasy football League draft going on. Great people. Great atmosphere. Great service. Had the oysters, rock shrimp and wings! Wings are air fried with great flavor. Oysters and shrimp are fresh and great taste. Very good beer selection. If you're a fan of IPA and Killian's along with the usual beers. Will definitely come again. The only drawback is all the University of Florida Gators stuff. Kidding. Go Irish!”

2 Ain't Miss Behavin' Sports and Tiki Bar

4.5 Superb 156 Reviews

1550 FL-436, Winter Park

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“Great food, great atmosphere”

3 Spatz

4.4 Superb 191 Reviews

1025 West Fairbanks Avenue, Winter Park

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“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....”

4 Casey's On Central

4.5 Superb 191 Reviews

50 East Central Boulevard Ste East, Orlando · 4.72 miles

“The atmosphere is relaxed, making it a perfect spot to unwind after a long day. The staff is friendly, attentive, and always provides excellent service. The drinks are well-made, the prices are fair, and the overall vibe is fun and enjoyable. Whether you’re stopping by for a quick drink or spending the evening with friends, this place is definitely worth a visit. Highly recommended! 🍻🎶”

5 Will's Pub

4.7 Superb 211 Reviews

1042 North Mills Avenue, Orlando · 3.17 miles

“LiL iNdieS n Will’s ROC ¡”

6 Jerry's Pub

4.7 Superb 84 Reviews

5825 South Orange Avenue, Orlando · 8.93 miles

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

7 Caboose

4.6 Superb 125 Reviews

1827 North Orange Avenue, Orlando · 2.97 miles

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“Walked into the Caboose Bar for a drink and found a great bar to frequent! Our bartender, Alexa, made good drinks and was very entertaining while aesthetically pleasing! The bar has pool tables, darts and good music also has a table or two outside front to sit and watch people go by since it's in a great location ! Recommend going to check it out if looking for a good time, would even feel comfortable going in solo as the people were very nice and inclusive of newbies! They also have some food items but we had already eaten. Love bars like this and bartenders like Alexa so wanted to recommend giving it a visit!”

8 Royal Bar

4.6 Superb 85 Reviews

5500 South Orange Blossom Trail, Orlando · 8.96 miles

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“The Bar Is Vibes All day. It’s just the Dj they have every other Friday He needs a New playlist Lowkey ssa. lol He’s my guy but if I tell him his music playlist sucks and it’s the same list week after weak. Maestro his name. Cool short dude. Always A good time and the Patrons are Amazing Crowd.”

9 Sloppy Taco Palace

4.5 Superb 347 Reviews

4892 South Kirkman Road, Orlando · 10.49 miles

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“Always Great place good food and drinks”

10 Hideaway Bar

4.5 Superb 267 Reviews

523 Virginia Drive, Orlando · 3.16 miles

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“If I could add more stars I would Shannon is the best vibe and I love hanging out during the day to experience it. She was literally there to replace beer before I could ever ask. Great customer service and a great place to be. I will suggest this bar to all my friends.”

11 Burton's Thornton Park

4.5 Superb 185 Reviews

801 East Washington Street, Orlando · 4.24 miles

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

12 George’s Hideaway

4.5 Superb 145 Reviews

5507 Edgewater Drive, Orlando · 4.46 miles

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“George’s Hideaway in Orlando stands out for great food, exceptional service, and a welcoming atmosphere. The staff makes you feel appreciated, and the local billiards players bring some excellent competition. The premium Blanton’s bourbon is another highlight. Whether you’re enjoying a game of pool or relaxing with friends, George’s is a place worth visiting. Thank you to the entire team for your five-star hospitality! #GeorgesHideaway #OrlandoBars #OrlandoBilliards #BlantonsBourbon #SupportLocalOrlando #OrlandoMusicScene #JirehMusicProductions #JMPAC”

13 Uncle Lou's Entertainment Hall

4.5 Superb 74 Reviews

1016 North Mills Avenue, Orlando · 3.21 miles

“Uncle Lou’s Entertainment Hall is exactly the kind of independent venue that gives a local music scene its personality. It has an intimate, DIY feel where original bands, touring artists, and passionate music fans all end up in the same room. Places like this remind you that great live music doesn’t need massive production—it just needs a stage, a welcoming crowd, and people who genuinely care about the experience. Orlando’s music community is stronger because venues like Uncle Lou’s continue to give artists a place to be heard and audiences a place to discover something new. Long live the independent rooms that keep live music authentic. 🍄”

14 Whiskey Lou's Lounge

4.2 Good 70 Reviews

121 North Bumby Avenue, Orlando · 3.87 miles

“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.”

15 Wally's Bar and Liquors

4.2 Good 148 Reviews

1001 North Mills Avenue, Orlando · 3.23 miles

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“Awesome place. Best place in town.”

16 Bullitt Bar

3.7 Good 109 Reviews

33 East Pine Street, Orlando · 4.69 miles

“Stopped by for a few drinks and had a great time. Jeff was our bartender and provided excellent service, friendly, attentive, and made us feel welcome. He even put on music we enjoyed, which made the experience even better. The atmosphere was fun, relaxed, and welcoming. We'll definitely be back! 🍻”