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Three Generations, One Unforgettable Trip: Our Kissimmee Getaway
Article and photography by Judi Cohen (TravelingJudi)
When I was asked what I wanted for my 70th birthday, I wasn’t thinking diamonds or luxury cars. Without hesitation, I said the greatest gift would be to plan our family’s first multi-generational holiday. We all cleared our schedules for a week in March 2025 and made it happen together.
A successful multi-generational family holiday required careful planning and discussions. My daughter lives in Toronto and my son in New York City, both juggling careers and babies (all under 3 years of age). Given the ages of the grandchildren, their parents wanted to stay in North America within a 3 to 4-hour flight from their homes. They also wanted to be able to prepare meals and go to restaurants, have activities close by for the children including playgrounds and swimming pools, and have a common area for all nine of us to be together during meals and relaxation hours.
Finding the Right Destination
With young children, staying within a 3-to 4-hour flight from home was a priority. Considering flight time and family needs, Florida stood out, and Kissimmee, the “Vacation Home Capital of the World”, became the clear choice. Located twenty miles south of Orlando, Kissimmee has vacation homes from two to 20 bedrooms that include themed bedrooms for toddlers, playrooms, private pools, home theatres and more.
The Perfect Home Away from Home
Our family of nine found the perfect six-bedroom vacation rental in Reunion Resort and Golf Club. More than just a place to sleep, it was an experience. It had a private pool and spa, a home theater, themed kids’ bedrooms, and dedicated play and lounge areas. Having space to spread out made all the difference, allowing everyone to recharge between outings while still enjoying shared moments together. We cooked meals in the well-equipped kitchen or on the outdoor BBQ, gathering around a spacious dining table where highchairs, provided by the resort, kept the little ones comfortable. Every day started with a breakfast with healthy choices to meet everyone’s taste including eggs, yogurt, coffee, toast, French toast, and lots of fresh fruit.
Several grocery stores were located less than five minutes from the resort. You can even pay to have the resort provision your house with food and drinks before and during your stay, arrange for a cook, and have cleaning services during your stay.
One of the important conveniences was having a washer and dryer, complete with detergent, iron and ironing board in the house. Ample clean bathroom and pool towels, and sheets were provided and could be washed as necessary.
Staying in a house for the week meant no packing or unpacking. It also allowed the toddlers to somewhat stay on their schedules.
On-Site Activities suitable for Toddlers
With toddlers, the waterpark provided hours of family fun from the morning to the late afternoon. The kids most enjoyed the pool that had a sloped shallow area where they could splash around in warm water. The sandy area next to the pool was also a favorite for little ones with games and toys. A lazy river flowed throughout the waterpark with inflatable donuts available.
To move around in the resort, there is a golf cart service operated like uber using an app. We preferred to drive our cars with baby seats to get around. It was safer and more convenient.
On-Site Activities for Adults
Reunion Resort offered a range of amenities including three championship golf courses and a top tier golf academy for private and group lessons, mini-golf, tennis, and pickle ball. I found time to brush up on my golf skills during a private lesson at the Golfzon Leadbetter Academy, while the children were napping.
On our last night, some of the adults went to the resort’s Chophouse restaurant. It had a traditional steak house menu including French onion soup, steak, and wedge salad with blue cheese dressing. When we left, the bar was hopping!
Exploring Kissimmee and Beyond
One of the best things about staying in Kissimmee is its proximity to theme parks, outdoor activities and a friendly downtown area.
Peppa Pig Theme Park & Legoland, were just a 20-minute drive from our resort and were perfect for toddlers, with attractions designed just for them. There were rides, Peppa shows, splash pads and a restaurant with a kid-friendly menu. Legoland includes a spectacular botanical garden, that was the former Cypress Gardens Park with a huge banyan tree planted in the 1930’s.
My son was keen to visit Sea World with his family. They purchased tickets ahead of time and were able to simply enter the gate. Within minutes, their children were smitten by the penguins and other cute sea animals.
We spent a full day in Downtown Kissimmee starting our day with coffee and a trio of breakfast tacos at Susana’s Cafe, a cozy welcoming restaurant with tables inside and out. The children loved playing on the swings and slides at Lakefront Park, on Lake Tohopekaliga. Lunch on the patio at Big John’s Rockin’ BBQ By the Lake ticked all the boxes with its delicious brisket and great sides of Mac n Cheese, sweet potato fries, and hot cornbread.
On our last day we slowed down, put on our hiking shoes and headed to the Tibet-Butler Nature Preserve, a 25-minute drive from Reunion Resort. It was a hidden gem, ideal for toddlers, and it was free! We did a comfortable 2-mile hike to Osprey Overlook.
While there were signs warning of the presence of snakes and alligators, thankfully, the only alligators we saw were baby ones in the education center.
Our multigenerational trip to Kissimmee was more than just a vacation. It was a time to reconnect, unwind, and create unforgettable memories together. Whether we were swimming in our private pool or at the water park, exploring nearby theme parks, or simply enjoying the comforts of our spacious vacation home, every moment felt special. With endless adventures just a short drive away and all the on-property amenities, relaxation was effortless. Kissimmee was the perfect place for our family getaway. We are already planning our next family adventure.
