Happy Hours in Maitland
Explore 10 happy hours in Maitland, Orlando. Find drink specials, food deals, and the best bar promotions.
Happy Hours
10
Updated
May 2026
Most Common Start
3 PM
Last updated: May 6, 2026
Editor's Picks
Maitland
Lazy Moon Maitland
Mon – Fri
·
2 PM – 8 PM
Beer
Cocktail
Mule
+3
Maitland
Luke’s
Mon – Fri
·
3 PM – 6 PM
$2 Off Draft Beers
Beer
Bubbly
Cocktail
+11
Maitland
Mandola’s Maitland
Mon – Fri
·
3 PM – 6 PM
Beer
Cocktail
Wine
+3
Maitland
Boku Sushi
Mon – Sat
·
4 PM – 5 PM
$3.50 Masago (Smelt Roe)
Beer
Sake
Wine
+2
Maitland
Packwoods
Tue – Fri
·
4 PM – 6 PM
$1 Off All Beers
Beer
Cocktail
Daiquiri
+5
Maitland
Parea Greek Tavern
Mon – Wed
·
4 PM – 6 PM
Beer
Cocktail
Wine
Maitland
Antonio’s Maitland
Mon – Fri
·
4:30 PM – 7 PM
$8 Eggplant Meatballs
Cocktail
"Espresso Martini"
"Old Fashioned"
+5
Maitland
Permanent Vacation
Tue – Thu
·
5 PM – 8 PM
Cocktail
Maitland
Parea Greek Tavern (Weekend)
Thu – Sun
·
3 PM – 6 PM
Beer
Cocktail
Wine
Maitland
Packwoods (Monday)
Mon
·
5 PM – 6 PM
$1 Off All Beers
Beer
Cocktail
Daiquiri
+5
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About Maitland Happy Hours
Maitland is a quiet, tree-lined suburb between Winter Park and Altamonte Springs with a small but quality happy hour scene. The strip along Maitland Boulevard and US 17-92 features a mix of neighborhood restaurants and upscale-casual dining. It is less flashy than Downtown or Winter Park, but the value is often better and the crowds are thinner — a genuine local secret for after-work drinks.
Frequently Asked Questions
How many happy hours are in Maitland?
There are currently 10 happy hours in Maitland, Orlando. This includes a mix of bars, restaurants, and lounges offering everything from discounted craft cocktails to half-price appetizers. We update this list regularly as new specials are added or existing ones change.
What time do happy hours start in Maitland?
Most happy hours in Maitland start between 3 PM and 5 PM on weekdays. The most common start time is 3 PM. Some spots offer earlier lunch-hour deals or later evening specials. Use the time filter above to find deals that match your schedule.
Are there weekend happy hours in Maitland?
Yes, there are currently 2 happy hours available on weekends in Maitland. Saturday and Sunday specials often include brunch deals, all-day specials, and late-afternoon happy hours. Filter by day above to see exactly what's running.