Upcoming Events in Osceola

KARAOKE MONDAY - POOLSIDE

12 January 2026

Kissimmee, FL

Secrets Hideaway Resort & Spa / Club Secret, 2145 E Irlo Bronson Memorial Hwy

VIP 90’s Prom Party New Year’s Eve!

31 December 2025

St Cloud, FL

The Black Squirrel Bookstore & Speakeasy, 1118 New York Ave

MINI MONDAY! 11x14 Canvas, Only $30!

29 December 2025

Kissimmee, FL

Painting with a Twist, 3038 Dyer Blvd

The Marketplace of Magic- Magical Miles Market

08 January 2026

Kissimmee, FL

Holiday Inn Resort Kissimmee by the Parks by IHG, 3011 Maingate Ln

Sunday FUNday! Midnight Zen!!

28 December 2025

Kissimmee, FL

Painting with a Twist, 3038 Dyer Blvd

Winter Pickleball Kids Camp | 12/22-1/2 | Orlando, FL

01 January 2026

Kissimmee, FL

Crush Yard - Pickleball Bar & Lounge, 7840 W Irlo Bronson Memorial Hwy

Winter Pickleball Kids Camp | 12/22-1/2 | Orlando, FL

02 January 2026

Kissimmee, FL

Crush Yard - Pickleball Bar & Lounge, 7840 W Irlo Bronson Memorial Hwy

Winter Pickleball Kids Camp | 12/22-1/2 | Orlando, FL

29 December 2025

Kissimmee, FL

Crush Yard - Pickleball Bar & Lounge, 7840 W Irlo Bronson Memorial Hwy

Old Town Exotic Cars & Coffee

22 February 2026

Kissimmee, FL

Old Town, 5770 W Irlo Bronson Memorial Hwy

Stitches of Love

26 December 2025

Davenport, FL

BellaTrae at Championsgate, 8411 Riverdale Ln