Trip Ideas for Your Kissimmee Vacation

Find inspiration for your trip to Central Florida with articles, lists and itineraries featuring things to do and places to explore.

Located minutes from Orlando, Kissimmee is your gateway to Central Florida’s must-do adventures: thrilling airboat rides, vibrant local festivals, family-friendly theme parks, and all the shopping and dining options you could dream of. The hard part is deciding where to start, but that’s where we come in.

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1 - 10 of 43 results

1 - 10 of 43 results

Corporate Meetings and other Special Event Services

Kissimmee's grandest home rentals are event-ready spaces that easily accommodate special occasions and corporate gatherings.

Kyla Kenedy sits to eat a plate of tacos while two cameramen film the shot. — Behind the scenes of the personal chef experience at Kyla's vacation home.

Kyla Kenedy: Top Luxury Experiences Around Kissimmee

Discover some of the most luxurious ways to unwind, indulge, and elevate your getaway in Kissimmee. Episode two of The Kissimmee Experience highlights several standout experiences that showcase the destination’s upscale side.

Two young children sit outside on bright turquoise chairs, enjoying ice cream at a table in front of a shop in Downtown St. Cloud, Florida. One child licks a waffle cone while the other eats with a spoon. — Sweet moments outside Pops Waffle & Ice Cream Shoppe in Downtown St. Cloud, where every cone comes with a smile.

Best Sweet Treats in Downtown St. Cloud

Craving something sweet? Discover the best dessert spots in Downtown St. Cloud, Florida, from colorful snowballs and waffle sundaes to chocolate-covered strawberries and more family-friendly treats.

Two young children sit outside on bright turquoise chairs, enjoying ice cream at a table in front of a shop in Downtown St. Cloud, Florida. One child licks a waffle cone while the other eats with a spoon. — Sweet moments outside Pops Waffle & Ice Cream Shoppe in Downtown St. Cloud, where every cone comes with a smile.

Top Dessert Spots in Downtown St. Cloud

From ice cream to chocolate-covered strawberries, find your next favorite sweet treat at a local bakery or dessert shop.

The Stained Glass Lady St. Cloud

Women-Owned Businesses in Downtown St. Cloud

Discover female-owned businesses in this Central Florida town, including clothing boutiques, trendy shops, and local eateries.

People stroll through a lively nighttime street market in downtown St. Cloud, with vendor tents, warm string lights, and shops glowing along the brick-paved street. — Downtown St. Cloud comes alive during its nighttime market, where visitors can shop, stroll, and enjoy the local vibe under twinkling lights.

Shopping Local at Downtown St. Cloud Monthly Market

The Downtown St. Cloud Monthly Market is a can't-miss event in Central Florida where locals and visitors gather to enjoy live music, browse local vendors, and try delicious eats.

A sunny tree-lined street with colorful homes and businesses in Kissimmee, Florida.

Celebration, Florida: A Town Like No Other

With tree-lined streets, captivating architecture, and a welcoming mix of shops and restaurants, Celebration invites visitors of all ages to explore.

Girl sitting in a rocket ship bed at a Kissimmee vacation home.

Themed Vacation Rentals in Kissimmee: Where Imagination Meets Home Comfort

With game rooms, bedrooms, and in-house theaters, these vacation home rentals make for a magical place to stay.

A modern luxury vacation home at dusk featuring a glowing blue resort-style pool with a waterfall, fire feature, palm trees, lounge chairs, and illuminated outdoor living spaces. — When the sun sets, the pool steals the spotlight. Evening swims glow a little brighter with fire features, flowing water, and room to unwind long after dark.

Top Tier at Reunion: Where the Stay Becomes Part of the Story

In Kissimmee, the Vacation Home Capital of the World®, where space, comfort, and flexibility define the way people travel, Top Tier at Reunion offers a refined way to settle in. These hand-selected luxury homes combine thoughtful design, elevated amenities, and personalized service with the freedom to experience Central Florida on your own terms, from theme park days to nature escapes and unforgettable meals shared around the table.

A man unloads his car in front of a vacation home as his family enters the home. — Plan your next stay in Kissimmee at one of our many vacation homes.

Where to Stay in Kissimmee: Hotels, Resorts, and Vacation Homes for Every Traveler

Kissimmee offers lodging to fit any need, from 4-star resorts to motels to vacation rentals. Learn more about all the ways you can stay in Central Florida!