Nightlife in Oldsmar

Standup-Comedy Show for Two with Option for Drinks at Snappers Grill & Comedy Club (50% Off)

Snappers Grill & Comedy Club

Snappers Grill & Comedy Club

Guests enjoy standup comedy from up-and-coming performers while sipping premium drinks

$24 $12

Two or Four Movie Tickets at Sunset Point Cinema Bar & Grille (Up to 38% Off)

Sunset Point Cinema Bar & Grille

Sunset Point Cinema Bar & Grille

Modern cinema with onsite bar and grille invites guests to eat burgers and sip wine before screening a first-run film

$6.50 $4.50

$39 for Date Night with Two Movie Tickets and $100 eGift Card ($124 Value*)

Ultimate Date Night Package

Online Deal

Create your own ultimate date with movie tickets and a $100 eGift Card for dinner

$124 $39

Distillery Packages for Two at The Florida Cane Distillery (Up to 33% Off). Two Options Available.

The Florida Cane Distillery

Historic Ybor

Hand-crafted, micro-distilled vodka made from 100% Floridian ingredients

$26.75 $18

$25for Gambling Cruise for Two with Well Drinks from Tropical Breeze Casino Cruise (Up to $50Value)

Tropical Breeze Casino Cruise

Port Richey

Against the picturesque backdrop of the Gulf of Mexico, passengers set sail along with casino games from slots and craps, to blackjack

$50 $25

Craft Beer Tasting Flights for Two or Four at Local Brewing Company Tap Tavern & Kitchen (Up to 50% Off)

Local Brewing Company Tap Tavern & Kitchen

LBC Palm Harbor

Sample local and international brews from a selection of 99 beers on tap

$36 $18

$20 for One General Admission to Chillounge Night on Saturday, November 19 ($35 Value)

Chillounge Night

Downtown St. Petersburg

Park transforms into an outdoor venue so guests can experience the 80’s and 90’s with fireworks & a 10-foot rotating disco ball with lasers

$35 $20

Beer, Pizza, and Optional Tour for Two or Four at Fat Point Brewing (Up to 49% Off)

Fat Point Brewing

Punta Gorda

Take an optional tour of the brewery and then enjoy pints of craft beer and cheese pizza in a taproom with five 60-inch TVs

$25 $15

Red or White Wine Flights with a Charcuterie Platter for Two or Four People at A Taste for Wine (Up to 40% Off)

A Taste for Wine

Downtown St. Petersburg

Charcuterie board spreads out the palate when paired with a bottle of red or white wine

$45.50 $30

Beer Tasting for Two or Four at Drip Craft Beer & Hard Cider Lounge (Up to 46% Off)

DRIP Beer, Cider & Wine Bar

DRIP Beer, Cider & Wine Bar

Sample four of this brewery’s over 50 craft beers, hard ciders, wines at a tasting, or feast on bar food, and cold-brewed iced coffee

$13.99 $9

Foghat on November 10 at 8 p.m.

Phoenix Productions of Florida Inc

The Cuban Club

70s arena kings treat fans to a fist-pumping set of bluesy, classic-rock staples such as “Slow Ride” and “Fool for the City”

$24.50 $5

Beer Flights and Appetizers for Two or Four at Tapz (Up to 42% Off)


Corey Ave

Friendly bar features one of the largest beer selections in the area: 57 craft brews on tap, 27 of which are by local makers like Motorworks

$20 $12

The Comedy Get Down feat. Cedric "The Entertainer" and George Lopez on Friday, January 20, at 8 p.m.

The Comedy Get Down Tampa

Amalie Arena

All-star comedy lineup includes Cedric ‘The Entertainer’, Eddie Griffin, D.L. Hughley, George Lopez, and Charlie Murphy

$64.40 $49.75

"Magic Men Live!" on November 6 at 8 p.m.

"Magic Men Live!"

Harborside Event Center

A story-driven, high-tech, all-male revue aims to bring the fantasies of contemporary women to life, from firemen to soldiers and warriors

$23.99 $19

Rock Hard Revue on October 14 or 28

Rock Hard Revue

Club Skye

All-male revue choreographed and directed by David Greenhouse of Chippendales in Las Vegas

$26.75 $10

Adult-Themed Halloween Party on Monday, October 31 at 9 p.m.

15th Annual Halloween Erotic Exotic Ball

Club Skye

Celebrate Halloween at this adult-themed party featuring erotic dancers, live DJ music, and a $1,000 costume contest

$15 $9

Magic Mike XXL: A Ladies Night Out Event on Friday, November 25, at 7 p.m.

Magic Mike XXL the Show

The Hall

A male dance revue comprised of musclebound hunks excites ladies with their sensual moves and showmanship

$26.97 $15

Beer Tasting for Two or Four at Big Top Brewing Company (Up to 50% Off)

Big Top Brewing Company


Small-batch craft beers including White Sands Wheat, Sun Coast Pale Ale, Circus City IPA, Intercoastal Amber, and seasonal brews

$28 $14

Beer Flights at St. Pete Brewing Company (Up to 46% Off). Two Options Available.

St. Pete Brewing Company

Downtown St. Petersburg

Small brewery in downtown St. Petersburg offers craft beer such as Grateful stout, Throat Punch IPA, and St. Pete orange wheat

$12 $7

Beer Flights for Two or Four at Surfside Taphouse (50% Off)

Surfside Taphouse


Beachside bar serving beers from Florida breweries such as Cigar City Brewing and JDub’s Brewing Company

$20 $10

Movie Theater Ticket Subscription Plans from MoviePass (Up to 37% Off). Four Options Available.


Online Deal

Smartphone app lets users reserve movie theater tickets at major theaters nationwide, saving them time and money

$17.99 $12.99

Scotch Irish Presents: Cryptic Wisdom and The Palmer Squares on Saturday, October 29, at 8 p.m.

Cryptic Wisdom and The Palmer Squares

Venom Custom Choppers

Tucson rapper that mixes alt-rock and hip-hop shares the stage with a Chicago rap duo known for their YouTube ciphers

$15.21 $8

$18 for $30 Worth of Craft Beer and Food at World of Beer

World of Beer

Downtown Sarasota

This spot pairs its impressive collection of rotating craft beers with an inventive menu that includes German pretzels, sliders, and more

$30 $18

The Big Hair Ball: a Totally Tubular '80s Party! on Saturday, November 5, at 7 p.m.

The Big Hair Ball: a Totally Tubular '80s Party!

The Ritz Ybor

Mighty Mongo plays a sing-along set of ’80s classics while costumed revelers dance, shoot Jell-O shots, and marvel at ’80s videos

$33.64 $19

Hookah with Mediterranean Food and Drinks for Two, Four, or Six at Fig Cafe (Up to 61% Off)


St. Petersburg

Mediterranean menu offers up meaty, vegitarian, and vegan options along with aromatic hookahs and tea amid sports on the TVs and live music

$38 $19

Suncoast Jazz Classic Festival on Sunday, November 20, at 11 a.m.

Suncoast Jazz Classic

Sheraton Sand Key Resort

Dave Bennett, the Ken Peplowski Quartet, Alfonso Ponticelli, Cornet Chop Suey, La Lucha, and Bill Allred headline the 26th annual jazz fest

$40 $19

Go Back to School with Alessia Cara: Know-It-All Tour Part II on October 27 at 7:30 p.m.

Alessia Cara

Ruth Eckerd Hall

Juno Award–winning singer-songwriter weaves powerful vocals into soulful R&B hits including “Here” and “Scars To Your Beautiful”

$56.25 $25

R&B Live Concert on November 26 or December 17 at 9:45 p.m.

R&B Live

Studio Movie Grill

R&B Live Soul Band plays smooth hits during an evening hosted by Shauny Rox and The R&B Live Band

$26.19 $15

CountryFlo Music & Camping Festival on Friday, November 4 and Saturday, November 5

CountryFlo Music & Camping Festival with Chris Stapleton, Thomas Rhett, & Gary Allan

Triple Canopy Ranch

Chris Stapleton, Trace Adkins, Jana Kramer, A Thousand Horses, and more at two-day country and camping festival

$103.17 $69

John Michael Montgomery featuring Ray Scott and Walker McGuire on Friday, November 11, at 6 p.m.

John Michael Montgomery

Coquina Beach

Crooner whose deep pipes and singles such as “I Swear” have reached more than 15 million ears (and hearts) performs a concert on the beach

$24.31 $12

Select Local Merchants

  • Buffalo Wild Wings
    For wings with a ton of zest, Oldsmar's Buffalo Wild Wings has got you covered. Eat healthy and feel better with Buffalo Wild Wings' low-fat and gluten-free plates. Drinks here are readily available, so you can enjoy a glass of red or try something new. This restaurant is great for families with kids. At Buffalo Wild Wings, diners can score happy hour deals. Whether you have a large or small group, Buffalo Wild Wings can accommodate both. Outdoor dining doesn't get much better than the beautiful patio at Buffalo Wild Wings. Bring your laptop here and tap into the complimentary wifi. Volume at this restaurant can reach upper decibels, so come prepared to raise your voice to be heard. Take it nice and easy at Buffalo Wild Wings, where casual dress is the rule of the day. If you're hoping to make a smashing impression at your next soiree, you can also have Buffalo Wild Wings cater for you. You can also grab your food to go. Drivers can park in the neighboring lot. Easily charge your payment using one of many major credit card options. Breakfast, lunch, and dinner are all on Buffalo Wild Wings' menu — you can stop by whenever the moment's right for you. Make your meal more fun with wings at Buffalo Wild Wings.
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    Oldsmar, FL US
  • Hennessy's
    Visit Hennessy's and indulge in some good old-fashioned American cuisine. It's always the right time to eat a delicious, healthy meal. Find one that won't disappoint at Hennessy's. Enjoy a drink with your dinner — this restaurant has a full bar to serve up a glass of wine, beer, or more. Round up your coworkers and head to Hennessy's for happy hour. Put on your dancing shoes! The restaurant provides plenty of space for those who love to boogie. Hennessy's can also cater your next party; call today for details. Drive to Hennessy's and find parking in the area. At Hennessy's, diners can make use of the safe bike rack. Deep pockets not required! Hennessy's takes pride in its over-the-top flavor and just-right prices. You can stop by at almost any time, since Hennessy's offers breakfast, lunch, and dinner. There's a classic American dish waiting to be made for you at Hennessy's.
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    Oldsmar, FL US
  • Rumba Island Bar & Grill
    Grab a bite at Oldsmar's Rumba Island Bar and Grill. Don't go thirsty during dinner! This restaurant also offers a splendid drink list featuring wine, beer, and more. Grab the kids when you head to this restaurant — its family-oriented menu and ambience are perfect for the whole clan. Rumba Island Bar and Grill puts the happy in happy hour. Rumba Island Bar and Grill offers patio seating in the warmer months. Get online gratis thanks to Rumba Island Bar and Grill's complimentary wifi. Weekends are busy at the restaurant, so be prepared for longer wait times. You can call it in, then carry it out. Restaurant customers can take advantage of the nearby parking options. Commute by bike to Rumba Island Bar and Grill and find easy bike parking. Dining at Rumba Island Bar and Grill will set you back about $30 per person on average.
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    Oldsmar, FL US
  • AMC Woodlands Square 20
    Enjoy the popcorn, chairs, and film at AMC Woodlands Square 20's movie theater in Oldsmar. Service and taste make a great restaurant, and that's why you won't be disappointed by this theater. Having trouble finding that family-friendly activity everyone will love? This theater is made for all ages, so little ones are welcome to come along, too. Check out the cinematic offerings from AMC Woodlands Square 20 in their open-air screening space. Parking is plentiful, so patrons can feel free to bring their vehicles.
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    Oldsmar, FL US
  • Rookies All American Sports Bar & Grill
    Ease your appetite with delicious bites from Rookies All Amer Sports Bar in Oldsmar. Take the comfort of your own home and add great grub from Rookies All Amer Sports Bar to create the perfect night. Don't waste time on public transportation! Bring your own wheels to the restaurant and easily park nearby.
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    Oldsmar, FL US
  • Whistle Stop Grill
    A sweet secret, Whistle Stop Grill serves a colorful array of ice cream options. Enjoy a drink with your dinner — this ice cream shop has a full bar to serve up a glass of wine, beer, or more. Little ones are free to make a mess at this ice cream shop, where the whole family is invited to dine. Cheers to the weekend! Whistle Stop Grill is serving up the fun! Whistle Stop Grill is a suitable restaurant for both large and small groups. Be sure to check out Whistle Stop Grill's outdoor seating when the climate is right. Complimentary wifi is available as well. Music lovers can enjoy live performances at Whistle Stop Grill as well. The ice cream shop picks up the most people during the week, so avoid the rush if crowds aren't your thing. Folks tend to dress down at Whistle Stop Grill, so keep comfort in mind when heading to the ice cream shop. Can't stay at this ice cream shop long? Pick up and go home. Free parking is readily available for hungry diners at Whistle Stop Grill. Whistle Stop Grill's diners can store their bikes safely at the rack around the corner. Prices run about average at Whistle Stop Grill. When you need something to cool you off, pay Whistle Stop Grill a visit and treat yourself to some tasty ice cream.
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    Safety Harbor, FL US