16 Best Dive Bars near Winter Park

Thirsty Gator Sports Bar • $
3040 North Goldenrod Road, Winter Park

Customers` Favorites

Dozen Oysters on the Half Shell
Nachos Chips with Salsa
Wings and Fries
Shrimp Cocktail
Steamed Oysters
Fresh Oysters
Chicken Wings
Boiled Shrimp
Gator Burger
Rock Shitmp

“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!“

4.6 Superb236 Reviews
2

Spatz

Spatz Sports Bar • $$
1025 West Fairbanks Avenue, Winter Park

Customers` Favorites

Sausage Pizza
French Fries
Hamburger
Wings

“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....“

4.3 Superb189 Reviews
Ain't Miss Behavin' Sports and Tiki Bar Bar • $
1550 FL-436, Winter Park

Customers` Favorites

Chicken Tenders and Fries
10 Boneless Wings
Philly Sandwich
Side Fries
Sliders

“Great food, great atmosphere“

4.2 Good155 Reviews
Casey's On Central Bar • $$
50 East Central Boulevard Ste East, Orlando - 4.72 miles

Customers` Favorites

Popcorn
Tito

“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! 🍻🎶“

4.6 Superb95 Reviews
Will's Pub Pubs • $
1042 N Mills Ave, Orlando - 3.17 miles

Customers` Favorites

Terrapin Frenchys Blues Blueberry Berliner Weiss
BBQ Pork Sandwich with Coleslaw
Funky Buddha Pineapple Beaches
Orange Blossom Pilsner
Dogfish Head Seaquench
Cigar City Jai Alai
Sierra Nevada Hazy
Whiskey Soir

“LiL iNdieS n Will’s ROC ¡“

4.7 Superb135 Reviews
Caboose Bar & Grill • $
1827 N Orange Ave, Orlando - 2.97 miles

Customers` Favorites

Mozzarella Sticks with Marinara Sauce
Fully Loaded Tots
Choo-Choo Sampler
Mini Corn Dogs
Chicken Lil's
Cabboose Wings
Meat Lovers
Beef Tacos

“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!“

4.7 Superb51 Reviews
Royal Bar Pubs • $
5500 South Orange Blossom Trail, Orlando - 8.96 miles

Customers` Favorites

Chips

“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.“

4.7 Superb18 Reviews
George’s Hideaway Bar & Grill • $
5507 Edgewater Dr, Orlando - 4.46 miles

Customers` Favorites

Spicy Italian Sausage with Peppers and Onions
Honey Barbecue Wings
Philly Cheesesteaks
Loaded Fries

“I grew up here.. just moved back from Jersey after 27 years.. so, I look like I'm from Jersey.. my bf and I wanted to check this place out. It was super layed back.. cool people and a chill environment. The bartenders were awesome!! I did have a problem with one of their reg“

4.5 Superb70 Reviews
Uncle Lou's Entertainment Hall Bar • $
1016 N Mills Ave, 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. 🍄“

4.5 Superb55 Reviews
Jerry's Pub Bar • $
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“

4.5 Superb31 Reviews
Hideaway Bar Bar & Grill • $
523 Virginia Drive, Orlando - 3.16 miles

Customers` Favorites

Chicken Tenders with Honey Mustard
Chicken Tenders and Chicken Wings
10 Lemon Pepper Chicken Wings
Chicken Quesadillas
Bacon Cheeseburger
Patty Melt Sandwich
Smash Patty Melt
Large Tater Tots
Mozzarella Sticks
Great Burgers

“On vacation at a near air b and b with my wife and 4 kids (9,8,5,4). This place got recommended by a local as a “place with games for the kids”.

Fusball, darts and golden tee kept the kids busy as mom and dad got a drink. Pro tip bring cash for the quarter machine.

Staff was overall friendly and tolerant of the kids. I don’t believe we ate here so not commenting on that.“

4.4 Superb132 Reviews
Sloppy Taco Palace Mexican • $
4892 S Kirkman Rd, Orlando - 10.49 miles

Customers` Favorites

Sloppy Tacos with Black Beans and Rice
Sloppy Tacos with Tots
3 Sloppy Taco Basket
Sloppy Tots Surpreme
Chips \u0026 Salsa
Chili Dog Basket
Sloppy Burrito
Rice and Beans
Chicken Wings
Cheese Bites

“Always Great place good food and drinks“

4.4 Superb190 Reviews
Wally's Bar and Liquors Bar • $$
1001 North Mills Avenue, Orlando - 3.23 miles

Customers` Favorites

Beer and a Shot 7 Tuesdays
Pizza Slut's Pizza
Knot Your Baby
PBR Tall Boy
Yuengling

“Awesome place. Best place in town.“

4.3 Superb76 Reviews
Burton's Thornton Park Bar • $
801 East Washington Street, Orlando - 4.24 miles

Customers` Favorites

Cheeseburger w Sweet Potato Fries
Belle Glos Dairyman Pinot Noir
Chimichanga Nationale
Slow Roasted Pork
Ceviche Del Dia
Avocado Fries
Chicken Wings
Quesadilla

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

4.3 Superb98 Reviews
Whiskey Lou's Lounge Bar • $
121 N Bumby Ave, Orlando - 3.87 miles

Customers` Favorites

Bacardi Shuts
Hero Fries
A Cookie
Wings

“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.“

4.2 Good71 Reviews
Bullitt Bar Bar • $
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! 🍻“

3.9 Good63 Reviews

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