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 36 results

1 - 10 of 36 results

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.

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.

Two women and a man walk down the streets of Celebration Town Center holding shopping bags. — Enjoy world-class shopping, entertainment, and dining in Celebration.

Unique Shopping in Kissimmee

Kissimmee has countless shops just waiting to be discovered. So if you're looking for high-end, luxury items or specialty souvenirs, you can find them all here.

Entrance to Orlando Vineland Premium Outlets

Complete Guide to Orlando Vineland Premium Outlets

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Two people hold hands outdoors, with a diamond engagement ring visible against a softly blurred green background. — A quiet moment of connection, where love takes center stage before the journey ahead.

Why Kissimmee is the Perfect Pre-Honeymoon Destination

Wedding planning can be stressful, which is why many couples are escaping for a pre-honeymoon getaway. Discover why Kissimmee, Florida, is the perfect destination for romance, relaxation, and adventure before the big day.

A family enjoys an airboat ride through the wetlands at Wild Florida, smiling and pointing at wildlife in the distance. — A family sets out on an exciting airboat adventure at Wild Florida, gliding across the headwaters of the Everglades to spot native wildlife and soak in Kissimmee’s natural beauty.

Unwrap the Joy of Kissimmee This Holiday Season

Discover how to make this holiday season memorable with unique gift ideas and unforgettable experiences in Kissimmee. Celebrate Small Business Saturday, explore charming shops, indulge in local flavors, and create lasting memories with your loved ones!

Playground at Kissimmee Lakefront Park

Day of Wellness and Relaxation Across Downtown Kissimmee & St. Cloud

Discover a day of relaxation in Downtown Kissimmee and St. Cloud, Florida. From lakeside strolls to yoga, tasty bites, and self-care, unwind in style.

Family walking down sidewalk at the Promenade at Sunset Walk — Enjoy shopping, dining, and entertainment at Promenade at Sunset Walk

Kissimmee Shopping Guide

From outlet malls to specialty boutiques to local favorites and national brands, there's a shopping experience for everyone in Kissimmee. Find out everything you need to know in this handy guide.