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 29 results

1 - 10 of 29 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.

Friends and family toast to a meal in Kissimmee

Alternatives to Cooking Thanksgiving Dinner

Thinking of doing something a little different this year? Here are a few ways to make this year's Thanksgiving unforgettable, rather than predictable!

Christmas tree in the Gaylord Palms Resort

Christmas at Gaylord Palms 2025: Rudolph the Red-Nosed Reindeer™ and More Holiday Fun

From Nov. 14, 2025 to Jan. 7, 2026, Christmas at Gaylord Palms transforms the resort into a holiday wonderland featuring Rudolph the Red-Nosed Reindeer™, dazzling lights, and family fun.

Beautifully decorated Christmas tree with red poinsettias, silver and gold ornaments, and twinkling lights inside a festive Kissimmee vacation home dining area. — Celebrate the holidays in style in a Kissimmee vacation home with sparkle, festive décor, and where the warmth of the season fills every room.

Creative Ways to "Wrap" a Vacation for Under the Tree

So you’ve decided to surprise the family with an unforgettable vacation to Kissimmee, Florida. Congratulations on winning the holidays! Your gift is sure to be a hit.

Santa's Little Helper cocktail

Holiday Cocktail Recipes from Kissimmee’s Best Mixologists

Warm up the holidays with festive drink recipes straight from Kissimmee’s top bars and restaurants!

Tinkerbelle arrives in Kissimmee and sits outside the Celebration Hotel

Tinkerbelle's 12 Days of Christmas

Follow Tinkerbelle the Dog on a pet-friendly holiday adventure in Kissimmee. Discover top attractions, restaurants, and places to stay where dogs are welcomed with open arms.

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!