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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Corporate Meetings and other Special Event Services

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

Family gathered around a dining table in a decorated Kissimmee vacation home, enjoying a festive holiday meal together by the Christmas tree. — Celebrate the holidays in comfort and style with family and friends in a beautifully decorated Kissimmee vacation home.

Top 5 Ways to Celebrate the Holidays in a Kissimmee Vacation Home

In the Vacation Home Capital of the World®, the holidays can be a little easier for you and much more memorable for the rest of the family.

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 two story Mediterranean style vacation home sits in the back ground, with a pool, chairs and fire pit in the foreground at dusk. — Enjoy the comforts of a Kissimmee Vacation Home Rental

Vacation Homes in Kissimmee for Spring Break

It won’t be long before spring has sprung, and that can only mean one thing: spring break! You can have everything you’ve ever dreamed of in a vacation, right here in Kissimmee.

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.

Wooden boardwalk winding through a peaceful cypress swamp surrounded by tall trees at Gatorland near Kissimmee, Florida. — Explore the natural side of Gatorland along its scenic boardwalk, where towering cypress trees and still waters showcase the beauty of Florida’s wetlands.

Influencer Itinerary: 4 Days of Outdoor Adventure & Indoor Leisure

Discover how Florida Instagrammer Angela Jones and her husband, Matthew Lewis, embraced the best of Kissimmee—from serene vacation-home downtime to standout moments in nature, dining, and after-dark fun. Their trip showcases just how effortlessly a Kissimmee getaway can balance relaxation with adventure.

Woman relaxing on a massage table wrapped in a white towel, surrounded by soft lighting, flowers, and candles in a tranquil spa setting. — Unwind and recharge with a soothing spa experience in Kissimmee.

Bump Up the Fun with a Blissful Three-Day Babymoon in Kissimmee

Calling all moms-to-be! Plan the ultimate babymoon in Kissimmee with this three-day itinerary filled with relaxation, pampering, and gentle adventures. From spa treatments to scenic nature spots, discover why Kissimmee is the perfect destination for a blissful pre-baby escape.

Modern two-story vacation home in Kissimmee at sunset, with warm exterior lighting, a spacious driveway, and an upper-level balcony. — A golden-hour welcome. This is what arriving in the Vacation Home Capital of the World feels like.

Top 5 Most Unique Amenities at The Bear’s Den Resort Orlando

Whether you’re visiting Central Florida to escape the cold weather or planning your next vacation with the whole family, The Bear’s Den Resort Orlando is the ideal spot for luxury accommodations.

Family eating a meal together next to a pool at their vacation home in Kissimmee, Florida. — Find the perfect home-away-from-home with Jeeves Florida Vacation Rentals.

Kissimmee’s Most Fun-Yet-Affordable Vacation Homes

Planning an affordable Central Florida vacation? No problem! Vacation homes don’t have to break the bank and can often offer more value than a hotel.

A family enjoys a sunny afternoon at a Kissimmee vacation home pool, with a father and son jumping in while two women relax on inflatable floats. — Making a splash! Enjoy poolside fun and relaxation at a spacious Kissimmee vacation home.

Kissimmee’s Most Enticing Vacation Home Pools

Here in Kissimmee, your dream vacation home comes with its very own splash zone! Forget cramped hotel pools and crowded water parks, these seven spectacular homes offer private pools that turn any day into a tropical getaway.