Orange Lake Resort (Kissimmee, FL – October 2025): Part 1

Hubs’ family has owned a timeshare in Kissimmee, Florida for over 40 years. I’ve been visiting the resort nearly every summer (and occasionally other times of the year) for the last 22 years. We have so many memories with family and friends, and with our own little family, at this spot. When the opportunity to own a couple deeded weeks arose, free of charge, we jumped on it. 

image credit: traveling with my bwuhs

I think I’ll do a separate post on timeshares as a whole so as to not clog up this post.

This particular trip was a near miss! Our pup had a soft tissue injury and we spent some time at the emergency vet the week before we left. He was on medicine for pain management (still is), and we were really worried about him. He stays with my parents when we go out of town, so I knew he would be in good hands, but he’s our baby. He rested a lot and improved every day, so ultimately we decided it was safe to leave him. 

Our travel day was soaked. There was traffic. The only fun part of the drive was playing Pokemon Go at rest areas and the obligatory trip to Buc-ees. We ended up at the gigantic gas station just after lunchtime so we grabbed some chopped brisket, sliced brisket, and pulled pork sandwiches. We also grabbed some snacks, candy, Icees, and Buc-ees Halloween t-shirts. 

image credit: traveling with my bwuhs

My favorite buy from Buc-ees was lap trays! These were an amazing addition to our road trip. Whether the boys are eating while we’re driving or parked in the parking lot, it gets messy. These lap trays were such a great solution. They were each able to fit their drink, grapes, and sandwich on the tray, and the high sides help keep it all contained. Worth every penny. 

image credit: traveling with my bwuhs

We finally arrived at the resort around 5pm, and there was about a 15 minute wait to check in. They have a trick where they check you in and then send you over to another desk to get your key cards activated. This is when they tell you you’re due for your Owner Update and try to get you to attend the sales presentation. From there you have your parking pass and key cards and are ready to go!

Our first night there, we went to our favorite Tex-Mex chain, Chuy’s (https://m.chuys.com/home), for dinner. The food is always delicious. This year, instead of the standard queso or guacamole app, we opted for the Appetizer Plate. The Bean and Cheese Panchos were amazing and I’m glad we stepped out of the box for that dish. Another fun feature of Chuy’s is their balloon animal artist! He was fantastic. We each got something special: a red Baymax, Chicken Jockey, Figment, and the rose from Beauty and the Beast. We always love the novelty of balloon art, but this time we were truly so impressed with his skills. 

image credit: traveling with my bwuhs

To top off our night, we had a view of the evening fireworks at Disney from the porch of our condo (albeit obstructed). It was a magical ending to our long travel day. 

image credit: traveling with my bwuhs

❤ Jen

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