For our stay in Florida, we based ourselves in Davenport, on the Highland Resort, in a four-bedroom villa complete with a games room and private swimming pool. It was perfectly located — outside of Orlando but only around 20 minutes from the theme parks, Kissimmee, and all the places we needed to be.
After picking up our hire car, a big Ford Expedition, and I mean huge, we made our way over to the villa. You practically needed a ladder to climb into the thing, and it was probably bigger than my Mercedes V-Class MPV that I drive day-to-day as a chauffeur at A52 Executive Cars.
The upside? Space. Loads of it. Three rows of seats, acres of luggage room, and total comfort for getting around Central Florida.
First Impressions of the Villa
First impressions were simple — wow.
The villa was incredibly spacious, with large en-suite bedrooms, a big open living area where we weren’t constantly bumping into each other, and a brilliant games room complete with a pool table, arcade machines and a dartboard.
Outside was the real highlight: a fantastic private swimming pool, a large deck area and a BBQ — perfect for lazy afternoons and evenings. The villa also backed directly onto a golf course, which would have suited golf-mad Dad and Oscar perfectly… had they actually found the time to squeeze a round or two in.
Local Life and First-Day Essentials
Local facilities were decent enough. There was a petrol station just outside the gated community, and while maps suggested the nearest supermarket was only a 15-minute walk away, typical American infrastructure meant walking simply wasn’t an option.
So instead, we jumped back into the Expedition and headed to Walmart, stocked up on essentials, and spent the rest of our first day doing exactly what you should do on day one of a Florida holiday — chilling in the pool.
Old Town Kissimmee
Throughout the two-week holiday, we spent a few afternoons and evenings in Old Town Kissimmee. This themed “old town” area has a surprisingly lively atmosphere, especially in the evenings, with shops, bars, restaurants and live entertainment.
One of the highlights was the regular classic car cruise nights, where American muscle cars and beautifully restored classics line the streets. It’s a brilliant place to wander around, grab food, and soak up a very particular slice of Americana — something I’ll cover properly in a separate post.
Old Town is also home to Florida’s longest, tallest and fastest wooden roller coaster. That fact alone meant it was a must-do for Oz, who happily ticked it off his ever-growing roller coaster “cred” list — something to do with an online roller coaster community that I’ll never fully understand.
Celebration: Quiet, Pretty and Very American
We also made a trip to Celebration, Disney’s carefully planned town just outside Orlando. It’s the polar opposite of the theme parks — quiet, laid back, and intentionally understated.
There’s not a huge amount going on, but the architecture is lovely, the streets are immaculate, and there are a handful of nice cafés, craft shops and independent stores. It was particularly popular with Mum, who enjoyed browsing the shops while the rest of us took in the slower pace of life.
Food, Fun and Florida Staples
The photos on this page are from various days across the holiday — playing crazy golf, eating far too much food, and fully embracing classic American dining.
We ate at all the usual suspects: Olive Garden, House of Blues, Applebee’s, IHOP and The Cheesecake Factory. One particular highlight was the look on Dad’s face when he ordered a Root Beer, fully expecting something closer to a pint of Bass back home in Derby… and instead discovering that classic American “beer” really isn’t beer at all.
Looking Back
In reflection, while Davenport and Kissimmee aren’t usually the kind of places we’d choose to stay, they offered plenty to do when we weren’t out exploring and turned out to be the perfect central base for everything we wanted to see and do.
Would we visit again? Probably not — but that says far more about us and our travel preferences than it does about the area itself.
It’s clearly hugely popular, judging by the number of people we drive to the airport through A52 Executive Cars, jetting off for their own Disney and Florida villa holidays.
Orlando Theme Parks & Beyond: A Florida Holiday for the Memory Bank
Magic Kingdom Orlando: One Day, Big Crowds and Questionable T-Shirts
