Bar guide · 5 picks · Updated August 2026

Best Bar Happy Hours in Winter Springs, FL

Winter Springs, FL has 5 bar spots with happy hour specials on the Winter Springs happy hours page, part of 14 Winter Springs menus with prices. Our #1 bar pick is Lei Kava, and deals start around $5 at Carrabba's Italian Grill. The 5 below count down from #5 to #1, each with its happy hour window, the deal, and a link to the full menu.

Bar spots

Happy hours

Menus with prices

Food deals

The 5 Best Bar Happy Hours in Winter Springs, counting down to #1

Ranked by a confirmed happy hour window, menu depth, and Google rating. Every pick links to the venue's full menu on DiscoverHappyHours.

Bar

5. Outback Steakhouse

4.3 (1,815)Bar

5891 Red Bug Lake Rd

7 items

See Outback Steakhouse menu →See the menu →

Bar

4. Khaos Sports Bar And Grill

4.5 (150)Bar

178 W State Rd 434

See Khaos Sports Bar And Grill menu →See the menu →

Kava Culture Winter Springs in Winter Springs, FL

3. Kava Culture Winter Springs

4.7 (256)Bar

1174 Tree Swallow Dr

See Kava Culture Winter Springs menu →See the menu →

Carrabba's Italian Grill in Winter Springs, FL

2. Carrabba's Italian Grill

4.5 (2,683)Bar

5820 Red Bug Lake Rd

Drinks

From 4 PM, Starting at $5, Until 6 PM Daily

3 items, 3 with prices

Select Items For Only$5Classic Red Sangria Blood Orange Margarita$5Bonizio Rosso Bonizio Bianco$5

See Carrabba's Italian Grill menu →See the menu →

#1 pick

1. Lei Kava

4.7 (147)Lounge Bar

5285 Red Bug Lake Rd #139

Drinks

25% off house teas & kava Daily · 4 - 7 PM Evening Happy Hour 25% off house teas & kava 12 - 1 PM & 8 - 9 PM Lei-Me Hours BOGO shells & teas · 25% off shots & slushies All Sunday Long Sunday Funday All day happy hour

14 items, 14 with prices

Kava Latte Espresso, milk, foam, kava$10Assorted flavorings$9Cherry Almond$6

See Lei Kava menu →See the menu →

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Happy Hours by Cuisine in Winter Springs

Restaurant(12)Italian(5)Other(4)Mexican(2)European(2)Chinese(2)Asian(1)

Frequently Asked Questions

Where are the best bar happy hours in Winter Springs?

We found 5 bar restaurants with happy hour specials in Winter Springs. Top picks include Kava Culture Winter Springs, Lei Kava, Carrabba's Italian Grill.

What kind of bar food specials are available during happy hour?

Bar restaurants in Winter Springs typically offer discounted appetizers, tacos, small plates, and specialty items during happy hour, often at 30-50% off regular prices.

What time is happy hour at bar restaurants in Winter Springs?

Most bar restaurants in Winter Springs run happy hour between 3 PM and 7 PM on weekdays. Some offer daily or weekend specials too.