Top 9 Places to Watch Live Entertainment in Kissimmee

See top spots for exciting live entertainment, from major bands to local live music to popular stand-up comedians and beyond. It's always showtime in Kissimmee!

People gather for live entertainment in Old Town Kissimmee

Old Town Kissimmee is a great place for live entertainment 

If there’s one thing everybody knows, it’s that there’s no substitute for seeing something live and in living color. Music, dancing, comedy — it’s always a little better when you’re enjoying it along with your friends and family. Here in Kissimmee, there are endless options for live entertainment, and we thought it’d be fun to share a few of our favorites with you. So hit the lights! It’s time for the top 10 places to watch live entertainment in Kissimmee. Ready? Set? Showtime!

Old Town Kissimmee

For the sheer number of options available to you, there’s no place quite like Old Town Kissimmee. This entertainment district is a throwback to the past Florida, complete with historical architecture, nostalgic storefronts, and plenty of fun and outdoor entertainment for the entire family. Of course, Old Town is best known for its exciting car shows and cruises. Three nights a week, this place roars to life and revs up the thrills with some of the coolest cars on the planet!

Friday nights, it’s the Muscle Car Show & Cruise where the horse-power runs hot through Old Town. You’ll see muscle and performance cars produced between 1964 and 1983, showing off their high-performance prowess for captivated motorheads. Then, on Saturday night, it’s time for the Classic Car Show where show-quality street rods, hot rods, and antiques produced before 1983 have their time to shine. This show has been entertaining locals and vacationers for over 30 years, so you know it’s a winner. Finally, Wednesday nights are themed nights with different styles and eras showcased every week. One week, you might be checking out Mustangs and classic Fords, the next week might be Jeep night, or perhaps pickup trucks will be on parade — the variety is half the fun!

But Old Town is more than cars. There’s also Family Movie Night every Sunday, Old Town Karaoke on Thursdays, and nightly live entertainment on Trophy Row Stage. 

Dr. Phillips Center for the Performing Arts

Are you the type who appreciates assigned seating to go along with your entertaining night out? Then you’ll love taking in a show at the Dr. Phillips Center for the Performing Arts. Here, you’ll find a fantastic assortment of performances, ranging from ballet to live theatre and Broadway shows, movie nights to interactive game shows. There’s also music, stand-up, and wonderful outdoor entertainment at the Frontyard Festival. Best of all, since you can purchase tickets well in advance, you never have to worry about finding the perfect seat to take everything in.

Bob Marley – A Tribute to Freedom

Bob Marley lovers unite — A Tribute to Freedom is an absolute must-visit during your vacation in Kissimmee. Located in Universal CityWalk, Bob Marley — A Tribute to Freedom is a venue inspired by the legendary frontman’s love of music. Every night, a live reggae band and DJ perform in the courtyard here, providing laidback tunes that are sure to make you “Get up, stand up” after you eat up your dinner.

CityWalk’s Rising Star

Would you rather be the entertainment than see the entertainment? Then CityWalk’s Rising Star Karaoke is the place for you. Backed by a live band, you can sing to your heart’s content and be the headlining act while friends and family cheer you on. First-timers and karaoke veterans alike are all welcome here. Who knows, maybe this is the place where you’ll catch your big break!

House of Blues

You certainly won’t be feeling blue after an evening out at the House of Blues in Disney Springs! You will, however, be singing some of your favorite rock, pop, and hip-hop hits on any given night — thanks to the amazing lineup of artists that regularly perform at this venue. National and international touring acts are fixtures here, and you can also enjoy free outdoor entertainment and live music in the House of Blues Courtyard nightly. With a diverse schedule of performers and a delicious southern-inspired menu, the House of Blues is sure to satisfy every appetite.

The Edison

Yes, The Edison is set in an abandoned power plant, but there is still plenty of energy and excitement here to charge up your evening of entertainment. There’s live music seven nights a week at The Edison, including sets by the Pearl Street Players — who love playing bluesy renditions of iconic hits. But it’s more than just music. You’ll also find burlesque dancers, amazing aerialists, and vaudevillian entertainment that is sure to leave you with a smile on your face.

Funny Bone Comedy Club

The Funny Bone Comedy Club hosts some of the funniest up-and-coming comedians in the country, as well as established names who are sure to tickle your funny bone. And trust us, the Improv knows talent. In fact, over the years, the Improv has helped launch the careers of everybody from Lily Tomlin to Adam Sandler. You never know who’ll be next to take the stage at the Funny Bone— where the stars of tomorrow shine brightly today!

Promenade at Sunset Walk

Promenade at Sunset Walk offers the perfect mix of dining, attractions, and, most importantly, outdoor entertainment. Sunset Walk hosts rock bands and acoustic sets, car shows, and best-of challenges on any given day. You can even listen in on live radio broadcasts. And if you’re spending your day at nearby Island H20 Live!, be sure to check out the live DJ days every Saturday.

Howl at the Moon

Now, this is a spot that is sure to get you howling! Howl at the Moon is an unforgettable entertainment experience complete with talented musicians performing classics from the 80s and 90s, as well as today’s hits. It’s high energy, and you’ll feel the party starting as soon as you arrive. Best of all, there’s plenty of room to shake your groove thang on the dance floor!

Let Us Entertain You

Your next trip to Kissimmee is sure to be full of toe-tapping, belly-laughing, sing-along fun — all thanks to our excellent entertainment options! We can’t wait to show you a good time while you’re here.

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