Osceola Entertainment

Enjoy live music by Dennis Haklar while you dine at The Wharf at Sunset Walk in Kissimmee, Florida.

A professional musician for over 30 years, Angelo Cicco performs a wide variety of musical styles from a repertoire of over 1,000 songs. Along with easily accommodating most requests, his guitar and musicianship skills allow for improvisation of intricate guitar solos and syncopated rhythms into every performance.

The @cityofstcloudfl annual Tree Lighting ceremony is Friday, December 6th 6-9pm. Find music, games, a snow slide for the kids, Santa & more! You wont want to miss this festive family night downtown. Activities & tree lighting will be located in front of City Hall.

The Wharf at Sunset Walk presents Dockside Dueling Pianos, live dueling piano music every Friday night at a NEW TIME: 7 – 10 PM. Request your favorite songs and enjoy nonstop live dueling pianos! Experience The Wharf’s unique atmosphere and terrific food and drink menu, including Oysters on the Half Shell, Shrimp & Grits, Shrimp […]

Mark your calendars— The 61st annual Christmas Parade presented by @st.cloudchamber and @cityofstcloudfl is coming up! Saturday, December 7th at 10am We hope to see everyone out for this festive community event. Stay and enjoy many local businesses before and after the parade.

Rhythm Me Up is a top 40 Orlando-based band of professional and passionate musicians. The band’s setlist is well taken care of by keeping high energy throughout the set, including the most famous songs from the ’70s till today’s hits, running through rock, pop, country, and reggae.

Give Back this Holiday Season! Please Join the Promenade at Sunset Walk in partnership with the Osceola County Sheriff’s Office Toy Drive Campaign. Sponsored by the all new Embassy Suites by Hilton Orlando™ Sunset Walk and Margaritaville Resort Orlando. A 2-toy donation is suggested for all car and truck owners, and spectators for the children […]

Enjoy live music by Sean Manvell while you dine at The Wharf.  

Fleetwood Mac mystically captures the essence of Fleetwood Mac, taking their audience on a nostalgic journey through the Rock & Roll Hall of Fame band’s timeless, multiplatinum hits. Join us at The Wharf at Sunset Walk for an unforgettable night of music and memories. With special guest Kayonne Riley. Experience the intimate atmosphere, state-of-the-art production, […]

Secret is out! We are having a PJ PARTAYYY! Wear your coziest Christmas pjs and join us on Monday December 16th from 5-8pm for, sips, bites, holiday cheer, and of course some amazing shopping! We can’t wait to see you there!

Enjoy the evening in Historic Downtown St Cloud. Find local makers, artisans and food trucks while walking throughout the downtown. Shops open extended hours for the event along with eateries & bars to dine. This event has become a local favorite and truly brings the community together. It’s a great opportunity to get to know […]

Nic Weatherly is an acoustic singer, songwriter, and instrumentalist focusing on funk, jazz, & rock.

The Wharf at Sunset Walk presents Dockside Dueling Pianos, live dueling piano music every Friday night at a NEW TIME: 7 – 10 PM.

Tasting Passports are $30 and include 20 tasting tickets, a specifically designed walking map of participating host businesses, and a keepsake wine tasting glass! During the event, host locations offer both one and multi-ticketed wines to sample. Downtown streets will NOT be closed for this event allowing plenty of parking. The Welcome Passport Check-in will […]

Pacific Rush is comprised of musicians from all over the world, joining their considerable experience and respective careers together to bring a signature West Coast vibe to listeners