The best things to do in Osceola County

23 things to do we’ve checked and stand behind — with the story on each one. Not a ranking; a record.

Browse another shelf: all of Osceola County’s best · Restaurants · Beauty · Bakeries & Sweets · Shopping · Nightlife · Home & Garden · Health & Wellness · Cafes · Arts & Culture · Hobbies, Books, & Crafts · Antiques, Thrift, & Vintage · Services · Parks & Outdoors

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Entertainment · 23 places · showing the latest additions first

Skip the endless planning and just drop into Fun Spot America Theme Parks - Kissimmee this week for Mine Blower’s 80-foot plunge into an…

2850 Florida Plaza Blvd (Kissimmee)

“Skip the endless planning and just drop into Fun Spot America Theme Parks - Kissimmee this week for Mine Blower’s 80-foot plunge into an inversion, those towering Skycoasters that feel like a near skydive, multi-level go-karts, kid-size rides, and a classic arcade.”

From the Four Corners newsletter, September 19, 2026

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Old Town

Entertainment

Old Town brings Kissimmee’s retro heartbeat back to life with weekly classic car shows, live entertainment, throwback rides, and an easy…

5770 W Irlo Bronson Memorial Hwy (Kissimmee)

“Old Town brings Kissimmee’s retro heartbeat back to life with weekly classic car shows, live entertainment, throwback rides, and an easy mix of local eats and quirky shops. Skip the mega parks and make a quick St. Cloud night of it this week, especially with Hamburger Mary's now serving up the laughs.”

From the Four Corners newsletter, September 20, 2026

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Amusement park featuring a sea of trampolines for flipping and tricks, plus a ninja course and a zipline.

2703 Osceola Pkwy (Kissimmee)

“Amusement park featuring a sea of trampolines for flipping and tricks, plus a ninja course and a zipline.”

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Historic Downtown Kissimmee is packed with upcoming festivals, the Kissimmee Valley Farmers Market, live entertainment, and a directory of…

421 Broadway (Kissimmee)

“Historic Downtown Kissimmee is packed with upcoming festivals, the Kissimmee Valley Farmers Market, live entertainment, and a directory of indie shops and eats that make wandering feel like treasure hunting, so build a little detour into your week and rediscover why hometown vibes always win.”

From the Celebration newsletter, October 4, 2026

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Whether you’re corralling kids or sneaking in some grown-up float time, Gaylord Palms Waterpark packs speed and drop slides, a multi-level…

6000 Osceola Pkwy (Kissimmee)

“Whether you’re corralling kids or sneaking in some grown-up float time, Gaylord Palms Waterpark packs speed and drop slides, a multi-level playhouse and slides for kids, a zero-entry pool, an action river, and the Wake Zone FlowRider, plus private cabanas and seasonal dive-in movies for easy weekend wins.”

From the Poinciana newsletter, September 8, 2026

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Skip the usual weekend loop and pop into Reptile World Serpentarium to meet a wild lineup of venomous and non-venomous snakes, plus other…

5705 E Irlo Bronson Memorial Hwy (St Cloud)

“Skip the usual weekend loop and pop into Reptile World Serpentarium to meet a wild lineup of venomous and non-venomous snakes, plus other scaly neighbors. The snake-handling presentation and Q&A with owner George Van Horn make it equal parts thrilling and actually educational.”

From the St. Cloud newsletter, September 23, 2026

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Swap your backyard hose for the five-acre splash zone at Reunion Resort Water Park. Drift the lazy river, send the kids down the big slide,…

7661 Tradition Blvd (Kissimmee)

“Swap your backyard hose for the five-acre splash zone at Reunion Resort Water Park. Drift the lazy river, send the kids down the big slide, then refuel with poolside bites and frozen drinks while you dominate giant Connect Four. Low-stress fun, high Florida vibes this week.”

From the Celebration newsletter, October 2, 2026

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Promenade at Sunset Walk is the all-in-one spot for legit local fun... restaurants from casual to splurgey, Studio Movie Grill, live music…

3251 Margaritaville Blvd (Kissimmee)

“Promenade at Sunset Walk is the all-in-one spot for legit local fun... restaurants from casual to splurgey, Studio Movie Grill, live music every night, plus Island H2O Water Park, Escapology and the Slingshot. Swing by this week for dinner, a set or some splashy chaos.”

From the Four Corners newsletter, September 25, 2026

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Designed by Robert Trent Jones Sr and Jr, Celebration Golf Club brings that classic, park-like vibe close to home with rolling fairways…

701 Golfpark Dr (Kissimmee)

“Designed by Robert Trent Jones Sr and Jr, Celebration Golf Club brings that classic, park-like vibe close to home with rolling fairways that keep things interesting without being punishing. Get some swings in on the range, tune up at the Golf Academy, then celebrate at the restaurant.”

From the Kissimmee newsletter, October 5, 2026

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Treat your swing to Falcon's Fire Golf Course, a Rees Jones designed public track with a legit practice facility, lessons when the slice…

3200 Seralago Blvd Suite 1 (Kissimmee)

“Treat your swing to Falcon's Fire Golf Course, a Rees Jones designed public track with a legit practice facility, lessons when the slice shows up, an award-winning golf shop, and the Falcon's Nest Restaurant for the inevitable post-round debrief... this week feels like the perfect tee time.”

From the Poinciana newsletter, September 20, 2026

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Intricate escape rooms themed after the seven deadly sins, pirates and more.

3255 Margaritaville Blvd (Kissimmee)

“Intricate escape rooms themed after the seven deadly sins, pirates and more.”

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Need an easy win this week? Celebration Town Center nails small-town charm with park-side strolls, indie boutiques, sweet-smelling…

610 Sycamore St #310 (Kissimmee)

“Need an easy win this week? Celebration Town Center nails small-town charm with park-side strolls, indie boutiques, sweet-smelling bakeries, and plenty of eats, plus a Sunday farmers market that turns browsing into "I guess we’re cooking tonight" energy.”

From the Four Corners newsletter, September 29, 2026

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Reunion Resort Golf Courses - Palmer & Watson serves two distinct tests of nerve and short-game know-how on rolling, well-bunkered layouts…

7599 Gathering Dr (Kissimmee)

“Reunion Resort Golf Courses - Palmer & Watson serves two distinct tests of nerve and short-game know-how on rolling, well-bunkered layouts designed by Arnold Palmer and Tom Watson.”

From the Celebration newsletter, October 13, 2026

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Historic Downtown St. Cloud brings real small-town charm with independent eats, boutique treasure hunting, and colorful murals you’ll…

903 Pennsylvania Ave (St Cloud)

“Historic Downtown St. Cloud brings real small-town charm with independent eats, boutique treasure hunting, and colorful murals you’ll actually stop for. Keep an eye on the Downtown Monthly Market for fresh finds and community vibes, perfect when you want something easy and close to home.”

From the St. Cloud newsletter, September 29, 2026

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Old Town Slingshot

Entertainment

If this week needs a hard reset, Old Town Slingshot will fling you into the Kissimmee sky at over 100 mph, gift you a split-second of pure…

located at, 5782 W Irlo Bronson Meml Hwy, Old Town Blvd (Kissimmee) · ✓ checked Aug 21

“If this week needs a hard reset, Old Town Slingshot will fling you into the Kissimmee sky at over 100 mph, gift you a split-second of pure silence, then send you back laughing with bragging rights and a new respect for your vocal cords.”

From the Four Corners newsletter, August 25, 2026

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Oaks National Golf Club brings 18 Karl Litten designed holes through century-old oaks, water, and regular cameos from heron and hawks, so…

1500 The Oaks Blvd (Kissimmee)

“Oaks National Golf Club brings 18 Karl Litten designed holes through century-old oaks, water, and regular cameos from heron and hawks, so your swing gets a view upgrade too. Warm up on the range, roll a few putts, then hit The Oaks Café and call it a day well played.”

From the Celebration newsletter, September 26, 2026

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Sneak in a midweek reset at Bonanza Golf & Gifts, with two 18-hole courses to keep the friendly trash talk rolling and a little summit that…

7761 W Irlo Bronson Memorial Hwy (Kissimmee)

“Sneak in a midweek reset at Bonanza Golf & Gifts, with two 18-hole courses to keep the friendly trash talk rolling and a little summit that turns golden hour into a vibe. Easygoing fun for couples, kids, and anyone craving a quick win close to home.”

From the Celebration newsletter, October 11, 2026

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Remington Golf Club

Entertainment

Whether you're learning or chasing pars, Remington Golf Club’s award-winning layout serves up generous landing areas, abundant water…

2995 Remington Blvd (Kissimmee)

“Whether you're learning or chasing pars, Remington Golf Club’s award-winning layout serves up generous landing areas, abundant water features, and scenic landscaping by Clifton, Ezell & Clifton. Grab a tee time, tune up at the practice facilities, then cap it with some on-site dining this week.”

From the Celebration newsletter, October 1, 2026

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A Johnny Miller Signature Design at Harmony Golf Preserve winds across 260 acres of wetlands, meadows, pines and ponds, which means zero…

7252 Five Oaks Dr (St Cloud)

“A Johnny Miller Signature Design at Harmony Golf Preserve winds across 260 acres of wetlands, meadows, pines and ponds, which means zero homes chirping at your slice. Extremely challenging yet scenic, it’s a go-to local track for lessons, clinics, and tournaments.”

From the Kissimmee newsletter, August 31, 2026

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El Yunque Community Splash Pad is the easy, low-stress way to let little ones burn energy and stay cool, with playful water features sized…

100 Astor Ct (Buena Ventura Lakes)

“El Yunque Community Splash Pad is the easy, low-stress way to let little ones burn energy and stay cool, with playful water features sized for younger kids. Pack a towel, let them run wild, and enjoy a breezy breather while they giggle themselves silly.”

From the St. Cloud newsletter, October 6, 2026

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St Cloud Twin

Entertainment

Built in 1917 and still charming, St Cloud Twin serves up first‑run digital films in a cozy, family-friendly theater that basically feels…

1111 10th St (St Cloud)

“Built in 1917 and still charming, St Cloud Twin serves up first‑run digital films in a cozy, family-friendly theater that basically feels like your neighbor's living room. Skip the megaplex crowds and make it your midweek reset, because a low-key night at the local screen beats another scroll marathon.”

From the St. Cloud newsletter, September 20, 2026

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Tree-lined fairways, a classic par-71 layout, and a 100 percent grass range make Kissimmee Bay Country Club an easy local pick when you…

2801 Kissimmee Bay Blvd (Kissimmee)

“Tree-lined fairways, a classic par-71 layout, and a 100 percent grass range make Kissimmee Bay Country Club an easy local pick when you need a quick reset this week. Sneak in practice on the chipping and putting areas, then wander the on-site golf museum for a little inspiration.”

From the St. Cloud newsletter, October 9, 2026

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