🏡💚 Corcoran Connect Realty Presents: May 2026 Events in Kissimmee – Flavors, Family, and Freedom!

May in Kissimmee is a vibrant mix of cultural celebrations, community service, and heartwarming traditions. From the shores of Lake Tohopekaliga to the bustling streets of the Vine Street district, there is always something to explore. At Corcoran Connect Realty, we believe that loving where you live starts with the community. As Your Real Estate Concierge, we’ve put together this guide to the best real-world events happening in Kissimmee this month! 🏡💚

Community Spirit & Service

1. Before the Storm 2026: Hurricane Preparation  

• Date: Saturday, May 2, 2026  

• Time: 10:00 AM – 2:00 PM
• Location: NeoCity OC Building  

• Address: 194 NeoCity Way, Kissimmee, FL 34744  

• Cost: FREEGet the whole family ready for hurricane season! ⛈️ This annual event provides essential knowledge on water management, safe battery disposal, and emergency kits to ensure Osceola County residents stay prepared.  

2. Vine Street CRA Cleanup Event  

• Date: Friday, May 15, 2026  

• Time: 8:30 AM – 10:30 AM
• Location: Vine Street CRA District  

• Address: 2211 W. Vine Street, Kissimmee, FL 34741  

• Cost: FREEHelp keep our city beautiful! 🧹 Join your neighbors for a community cleanup. It’s a great way to make a positive impact, connect with local leaders, and learn about the future redevelopment of the Vine Street area.  

3. Let's Go Senior Expo!

• Date: Tuesday, May 19, 2026  

• Time: 10:00 AM – 12:30 PM  

• Location: The BEV Event Center  

• Address: Kissimmee, FL  

• Cost: FREE (Registration Required)A morning of food, fun, and fellowship! 🩺 Seniors can meet with dozens of local businesses and service providers while enjoying a FREE brunch and live entertainment.  

Food, Festivals & Family Traditions

4. Taste of Kissimmee

• Date: Friday, May 8, 2026  

• Time: 5:00 PM – 9:00 PM
• Location: Kissimmee Lakefront Park (Ruby Plaza)  

• Address: 201 Lakeview Drive, Kissimmee, FL 34741  

• Cost: FREE Admission (Food/Drinks for purchase)Celebrate the diversity of our community through food! 🌮🎶 Enjoy dishes from local restaurants, live music, and cultural performances that highlight the incredible flavors of Kissimmee.  

5. Mother & Son Dance: Sneaker Ball Masquerade  

• Date: Saturday, May 9, 2026
• Time: 5:00 PM – 8:00 PM
• Location: Chamber's Park Community Center
• Address: 2380 Smith Street, Kissimmee, FL 34744  

• Cost: $5 per personMoms and sons, it’s time to party! 👟🎭 Dress in your best kicks and a touch of mystery for this year's "Sneaker Ball Masquerade." It’s an evening designed to create unforgettable memories through music and dancing.  

6. PrideFest Kissimmee

• Date: Saturday, May 30, 2026
• Time: 12:00 PM – 5:00 PM
• Location: Kissimmee Lakefront Park  

• Address: 201 Lakeview Drive, Kissimmee, FL 34741  

• Cost: FREEJoin us in the heart of Kissimmee to celebrate diversity and inclusion! 🌈 This community event features live performances, local vendors, and family activities honoring the contributions of the LGBTQIA+ community.

Honoring Our Heroes: Memorial Day Weekend

7. Orlando VA Memorial Day Ceremony

• Date: Friday, May 22, 2026
• Time: 10:00 AM
• Location: Orlando VA Medical Center (Outdoor Amphitheater)
• Address: 13800 Veterans Way, Orlando, FL 32827 (Lake Nona Area)
• Cost: FREEA solemn tribute to the brave men and women who gave their lives in service. 🎖️ This ceremony features keynote speakers, the Presentation of Colors, and musical performances. Shuttles are available to assist guests.

8. Memorial 4-Day Weekend at Sunset Walk  

• Date: Friday, May 22 – Monday, May 25, 2026  

• Time: Starts 5:00 PM or 6:00 PM daily
• Location: Promenade at Sunset Walk
• Address: 3251 Margaritaville Blvd, Kissimmee, FL 34747
• Cost: FREE Admission & ParkingFour days of nonstop entertainment honoring our military. 🇺🇸 Enjoy live music from bands like The Rundown, DJ sets, street performers, over 30 restaurants, and the "Promenade Racing" Car & Truck Show.

Whether you’re enjoying the sunset at the lakefront or participating in a community cleanup, Kissimmee is a city that thrives on connection. At Corcoran Connect Realty, we are honored to be your local experts in Osceola County. If you are ready to buy or sell your home, let Your Real Estate Concierge handle every detail while you enjoy the incredible lifestyle of Kissimmee! 🔑💚