Live music in Kissimmee, FL

Jason 'Gote' VanDeMaat brings live music to the Tommy Bahama Marlin Bar in Winter Park, Florida. The performance features laid back tunes with a coastal feel, creating a relaxed, fun filled atmosphere.

C&E Live Music brings a lively dueling pianos show to Rock 'N Rev Ocoee, filled with singalongs, laughs, and interactive fun. Two pianists face off at the keys and take requests from the crowd, covering classic rock, country, pop hits, nostalgic throwbacks, Disney favorites, and big anthems. Expect upbeat performances, quick wit, and plenty of audience participation that keeps the energy high from start to finish. Suitable for friends, families, date nights, and music lovers of all ages. Presented by C&E Live Music.

Puzzles Entertainment hosts a weekly Jukebox Bingo game at The Friar Tuck that mixes music recognition with classic bingo. Players listen to songs, mark their cards, and keep the energy high with singing and dancing. The game features four rounds with four winners, and prizes include free drinks and gift certificates.

Puzzles Entertainment brings a musical twist on bingo to The Friar Tuck, blending a music quiz with classic gameplay. Expect lively music, singing, dancing, and friendly competition. There is no cost to participate. Prizes include complimentary drinks and gift certificates, with four rounds and a winner in each.

Experience a music-fueled spin on bingo at 4Corners Tavern with Puzzles’ Jukebox Bingo, presented by Puzzles Entertainment. The game blends familiar tunes with classic bingo play, featuring four rounds built around four different playlists that lead to four winners and four prizes. Songs cover a wide mix of decades and genres, and players mark titles on a digital bingo card as they listen, competing to be the first to call bingo. Bring a charged phone or tablet to use as your card. Friends can come along, and food and drinks are available to order during the fun.

Readers of The Clermont Sun named Butchie’s Karaoke Night at The Friar Tuck the best in South Lake County. Hosted by Butchie, the singing bartender, this gathering adds a playful twist with the Karaoke Wheel of Terror. Spin the wheel, sing the song it selects, and receive a free drink for taking the challenge. It happens every 5th Wednesday of the month and promises a lively stretch of karaoke fun.

Settle in for live music as Davey Gilmore performs a mix of Britpop and UK classics.

A weekly karaoke experience at Old Town puts the spotlight on anyone who wants to sing, welcoming polished performers and off-key enthusiasts alike. Take the mic, share a favorite song, and enjoy a friendly atmosphere where every voice is celebrated. The event takes place on Old Town’s Main Stage beside Southern Breeze, offering a fun opportunity to step up, perform, and savor a moment in the spotlight.

Wind down after work in Baldwin Park as the village center transforms into a lively open air market experience. Explore a curated mix of local vendors for unique finds, enjoy food and drinks from neighborhood favorites, and take in live entertainment while relaxing with friends and family. Admission is free and everyone is welcome. The event is kid friendly and leashed pets are invited. Whether planning a date night or a casual outing with the whole crew, expect shopping, dining, music, and an easygoing community vibe in a beautiful setting. Vendor applications are available.

Funtastic Depot transforms into a neon themed celebration for families, teens, and friends, featuring live DJs, arcade games, climbing walls, and a grand finale show. Guests can jump, dance, and compete while neon lights set the mood across the park, and unlimited attractions are included. More than a trampoline park, it offers a Friday night tradition in the making.

AEG Presents brings Too Much, Not Enough to The Plaza Live, featuring Daði Freyr with Bríet. This is an all ages event.

Recommended for ages 17 and up, this cult-favorite stage show fuses audacious comedy, horror movie nostalgia, and high-octane rock into a wild night at the theater. Evil Dead The Musical reimagines the beloved franchise with demons, chainsaws, familiar musical moments, and gleefully over-the-top fun, arriving right in time for spooky season. Central Florida Vocal Arts and Opera del Sol work to build a kinder, more connected community by expanding access to the performing arts through quality productions and transformative education, changing lives, one voice at a time.

Start the weekend at Out-n-About Bar and Music Lounge with a rock night that keeps the dance floor moving. Share laughs with friends and grab a bite while the music keeps things going.

Promenade at Sunset Walk teams up with Real Radio 104.1 for the eighth annual Best of Challenge, Signature Edition, hosted by the cast of The Jim Colbert Show with DJ Scotty B. The cast returns as celebrity hosts, including Rauce Padgett. Eleven venues from Promenade at Sunset Walk, Margaritaville Resort and Encore Resort present their standout signature creations. VIP tasting admission is $20 and gives participants the chance to sample dishes from all 11 competitors and vote for their top three, and VIP tasting and judging packages are limited. Central Florida foodie influencers and media will select the Critics Choice, and the Jim Colbert Show cast will lead the Listeners Challenge competition. Spectators are admitted at no charge, and live entertainment and event activities are hosted by The Jim Colbert Show and DJ Scotty B. Luxury talent dressing rooms are provided by Giant Recreation World in Winter Garden. After the challenge, live music by Osaka Fall, the Promenade Artisan Market and Show Car Saturday Nights are featured.

Five-time Grammy winner Lalah Hathaway appears in an intimate lounge setting for four shows over two nights. As the daughter of Donny Hathaway, her musical roots run deep, and her collaborations span Pharrell Williams, Kendrick Lamar, and Dr. Dre. She has also shared stages with Prince, Stevie Wonder, and Herbie Hancock. Hathaway is tied with Beyoncé for the most Grammy wins in Best Traditional R&B Performance, with three each. Expect an evening of rich vocals and timeless songs, with sounds grounded in R&B, jazz, and soulful expression.

An all-80s dance party takes over Blue Bamboo Center For The Arts, led by Ricky Sylvia with The Buzzcatz and featuring guest vocalists Carmen Harrell-Ferreira and Naome Bradshaw. Attendees are encouraged to wear their best 80s MTV inspired outfits.