The best bars & nightlife in Winter Park

Bounce House Social Eats is serving refined cocktails and seriously fun comfort food, from Drunken Taters and Larry Curds to jumbo wings in…

12100 Challenger Pkwy (Orlando)

Orlando Comedy Club packs a true comedy room inside Calypso Bar & Grill near I-Drive with stand-up shows, local showcases, weekly open…

6300 Parc Corniche Dr (Orlando)

Festive pub offering myriad beer options, wine & TVs tuned to sports, plus live music.

781 N Alafaya Trail (Orlando)

American grub is served at this lively hangout with nightly live music, open-air seating & TVs.

4120 S Orange Ave (Orlando)

Wine shop offering a curated selection of Italian and American wines plus cheese boards.

4745 S Orange Ave (Orlando)

Cozy lounge serving a wide range of bubblies, along with beer and wine.

480 N Orlando Ave Ste 133

Casual locale with weekly live music offering tapas, charcuterie plates, Italian dishes & wine.

444 W New England Ave #119

Laid-back spot with a wide variety of canned and bottled brews alongside growlers and kegs, plus wine.

531 Virginia Dr (Orlando)

Traditional Puerto Rican specialties offered in an easygoing setting with vibrant decor.

7101 S Orange Ave (Orlando)

Cozy wine bar offers fine varietals by the glass, flight & bottle, plus light fare & patio seating.

430 E Central Blvd (Orlando)

Clubhouselike American haunt serving burgers & drinks in warm digs on the Dubsdread golf course.

549 W Par St (Orlando)

Oysters, grilled, baked and Rockefeller options are served at this seafood joint with a wine list and beer menu.

1957 S Alafaya Trail (Orlando)

Trendy, family-run eatery and wine bar, with self-serve beer and wine taps.

14383 Narcoossee Rd (Orlando)

Upscale chain serving New American fare paired with house-label wines in a contemporary setting.

8005 International Dr (Orlando)

Antique-filled, parlor-style cocktail lounge with boutique spirits & small bites.

3 Phoenix Building, 30 S Magnolia Ave (Orlando)

Relaxed store & wine bar featuring a selection of rare vintages plus indoor & outdoor seating.

1215 Edgewater Dr (Orlando)

Lounge-y cocktail bar for craft brews, cocktails and spirits, plus a refined atmosphere and decor.

37 N Orange Ave (Orlando)

Neighborhood bar housed in a furniture store offers microbrews & boutique wines, plus patio seating.

1800 N Orange Ave (Orlando)

Craft cocktail bar specializing in whiskey and other spirits in a cozy, hip setting.

650 S Capen Ave

Local bar & grill chain offering a classic setting for American pub fare & sports on TV.

547 N Alafaya Trail (Orlando)

Wine bar popular for dates, with craft beer, local art and live tunes.

1110 Virginia Dr (Orlando)

Traditional, dark-wooded Irish tavern featuring hearty pub grub, beers on tap & bands on weekends.

544 W Fairbanks Ave

Comedians from TV and the movies perform at this regular Saturday night show.

4270 Aloma Ave

Improv comedy club inspired by the TV show "Whose Line Is It Anyway?," with uncensored content.

1010 Virginia Dr (Orlando)

Cool speakeasy with a warm, swanky vibe specializing in imaginative craft cocktails.

1288 N Orange Ave

Classic-style pub & eatery with a long menu of sandwiches & pizza, plus a selection of craft beer.

3400 Edgewater Dr (Orlando)

Speakeasy-themed wine bar offering beer, cigars, and live music, plus happy hour drinks.

163 E Morse Blvd

Entertainment spot inside The Corner featuring comedy shows every Friday and Saturday night.

70 N Orange Ave (Orlando)

Casual eatery in the Rosen Centre Hotel featuring tapas-sized Mexican bites & varieties of tequila.

9840 International Dr (Orlando)

Rustic-casual venue with 100+ wines to taste via a machine dispenser, plus artisanal cheese & tapas.

270 S Park Ave

Casual kiosk in an outlet mall for Armenian wines that can be sampled, plus frozen specialties.

8200 Vineland Ave Unit 281 (Orlando)

Local comedians face off in improvised scenes, sometimes based on suggestions from the audience.

55 W Church St #211 (Orlando)

All-you-can-eat restaurant blending Korean BBQ and hot pot dishes with a tablet-ordering system.

5535 S Kirkman Rd (Orlando)

Casual New American kitchen & wine bar offering bites & wines on tap in spacious, modern surrounds.

110 S Orlando Ave #12

Stylish, password-entry speakeasy serving craft cocktails in intimate surrounds with a patio.

27 E Pine St (Orlando)

Cozy, prohibition-themed lounge featuring cocktails, tapas and light jazz, plus a secret speakeasy entrance.

13526 Village Park Dr Unit 208 (Orlando)

Family-friendly American restaurant with a full bar, TVs, a game room & occasional live music.

2631 S Ferncreek Ave (Orlando)