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

Corporate Meetings and other Special Event Services

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

Anisa Benitez joins the cast of The Kissimmee Experience.

Anisa Benitez: Reconnect With Yourself In Kissimmee

Creative wellness advocate and content creator Anisa Benitez, known for her No Starving Artist podcast and mindful storytelling, explores Kissimmee’s relaxing side in The Kissimmee Experience — from goat yoga and spa days to sustainable wine tastings and quiet moments of reflection.

Group of friends celebrating the holidays with sparklers and wine around a festive dinner table decorated with candles and Christmas lights. — Ring in the holidays with good food, bright lights, and even brighter smiles during your stay in Kissimmee.

Host Your Next Meeting in Kissimmee and Experience Holiday Magic

Combine productive meetings with the festive spirit of Central Florida’s top attractions and local holiday events.

Woman relaxing in pool

Relax and Recharge: Your Guide to Wellness in Kissimmee

Unwind and rejuvenate in Kissimmee with top resorts, serene outdoor experiences, and mindful activities. Discover the perfect balance of relaxation and adventure in Central Florida.

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!