Good morning, Kissimmee.

Governor DeSantis announced a new partnership with Florida Prepaid at Toho High School in Kissimmee on April 23, enabling parents to open a 529 college savings account when enrolling their children in the Voluntary Prekindergarten program — a step toward simpler, more affordable college planning.

Live Music with Rafael Rodriguez

1-5 p.m. — Salty Rim Bar & Grill — Free entry — Enjoy live tunes by Rafael Rodriguez while sipping and savoring the ambiance at Margaritaville Resort Orlando.

Freestyle Classics Dance Party

7-11 p.m. — Pargh Event Center — $30 GA, $360 VIP — Dance the night away to the greatest 80’s & 90’s freestyle hits spun live by top DJs.

Orlando City B vs. Crown Legacy FC Parking

7-8 p.m. — Osceola County Stadium — $25 each — Book guaranteed parking for an exciting soccer match in Kissimmee.

Cinco De Mayo Street Party

3-10 p.m. — Promenade at Sunset Walk — Free entry — Celebrate Cinco De Mayo with live music and fun festivities in Kissimmee.

Mother's Day Brunch Cruise

12-2 p.m. — Old Florida Riverboat Company — Cost info not provided — Celebrate Mother’s Day with a brunch cruise featuring scenic views and live music.

Club D3 Charity Golf Tournament

8 AM – 5 PM — Falcon's Fire Golf Course — Participation fee required — Enjoy a fun-filled day of golf, community bonding, and Club D3 spirit.

Memorial Day Weekend Celebration

5-11:30 p.m. — Promenade at Sunset Walk — Free entry — Enjoy live music, artisan markets, and car shows while honoring military heroes over a fun-filled four days.

Kissimmee Collectorfest Spring 2026

9 AM – 12 PM — Osceola Heritage Park — Admission details pending — Explore over 20,000 square feet of collectibles hosted by Florida Toy Shows.

Y2K Prom at Dreamers & Creators Original Market

11 a.m.-4 p.m. — Events Center — VIP tickets required — Relive the magic of DCOM with a prom night full of fun, dance, and exclusive goodies.