Five in Florida (Travelling with a toddler) Part 2 – How to book

How to book

So you may have already seen my post on pre-planning a trip to Orlando. I also wanted to write about how we tackled the booking stage. First though, my advice would be to bookmark everything. If you find an interesting article or a blog post that applies to you (like this one perhaps) bookmark it. I made a specific ‘Florida’ folder and saved everything. Trust me, after the 15th perfect looking villa you won’t remember which one is which! I also added notes on the bookmark title, such as ‘cheaper but check location’ or ‘more photos of above villa here’. This really helped when my bookmark list became longer than my laptop screen. Even if you think ‘oh I’ll remember where I found that helpful page’, bookmark it anyway. After a good nights sleep you’ll be cursing yourself if you can’t find the site again.

Now, taking a trip to Orlando with a toddler is a big deal whichever way you look at it. Kids just take SO much thought, because lets face it – they pretty much can’t do anything for themselves. Luckily, thinking and planning are my middle names, and I love stuff like this!


Naturally the first thing we considered about this trip was when to go. For us, queue times were a big deal. We were extremely flexible on the time of year, but we all agreed that we just wouldn’t want to go if the majority of our holiday was spent waiting in lines. Believe it or not, we’re pretty antisocial people and don’t like big crowds. Yup, I can hear you thinking ‘WHAT THE?’ from here! Orlando seems like a crazy choice, right?! Well.. yes and no. With the right planning and research, I was pretty sure we’d make it work – and we did 😉

I won’t go into every detail of all the things I researched because this would end up being a book, but my first tip on planning this kind of trip would be to look at some Disney/Universal crowd calendars, such as this one from Undercover Tourist. I checked at least two different sources and cross referenced them with actual crowd numbers from the year before to work out which months would be quietest (relatively speaking of course!)

_1060344Once we decided on November, I then did a search for ALL events happening in that month in Florida – public holiday’s, closures, Disney specific events (such as the Food and Wine Festival in our case), events at Universal. Anything and everything that could have an impact on our trip. I also looked at average weather reports for the month, as well as historical weather details from previous years. We didn’t want it to be so hot that we’d spend our holiday dashing Willow from shade to shade, but equally we didn’t want to spend it under an umbrella either. All of this helped us choose our exact days to book, and gave us some indication of the sort of weather we should expect and how to prepare for that.

As our intended dates were over a year away we couldn’t check flights, so instead I checked the prices for the same month of the year before just to be sure they weren’t out of budget. Everything looked good so we then started talking about where to stay.

Now as much as it’s quite nice to be in a hotel where someone comes in and tidies the bed for you every morning, it just wasn’t practical with a toddler. When Willow goes to bed absolutely exhausted from her days at Disney, in a hotel we’d all have to go to bed too. Plus I didn’t like the thought of my mum having to go off to her own hotel room, and Scott go off to his at the end of each day. This holiday was about us all spending time together. A rental villa just ticked all the boxes for us – a space where Willow could have her own room and not be disturbed by us adults having a chat about the days events while scoffing ice cream! A private pool where we didn’t have to lay out towels to mark our space, plus a washing machine so we could continue using cloth nappies – yes, this was important too!

I lost count of the number of villas I looked at, but my tip would be to think carefully about what you want.

  • Location – No-one wants to drive an hour to and from the parks with a toddler who might be having a bad day. Also consider the route to and from Disney. Is there a good alternative route if the I-4 is solid? Look on Google maps – Is there anything in walking distance? How far is the nearest supermarket? (You already know how long it takes to make a ‘quick trip in the car’ with a child!)
  • Facilities – Will you have time to use a private pool? – and does it have a child safety fence? Do you need a washing machine and/or microwave? Does it come with stair gates/cot/high chair? Do they provide a buggy, umbrellas, cookware, towels? Is there an internet connection and/or kids TV channels so you can pacify your little one with a familiar programme while you dash around in the morning?
  • Layout – Will you need to bring/buy a baby monitor? Are there childproof alarms/locks on all external doors? (especially out to the pool) Are there an hazards for an over-tired, over-exited child who might be swinging a Woody doll around?


There is certainly a lot more to think about when you add a small child into the equation, but we found that most villa owners have already thought of everything and are more than happy to answer questions. We eventually chose this place, and it was absolutely perfect.

Although the obvious part of the holiday to book first may seem like the flights, I’d spent so much time finding us the perfect location that we didn’t want to lose it. We actually put our deposit down on the villa first, then the flights, car hire and airport parking, and theme park tickets last. It was a bit of a risk, but the villa owner was flexible in terms of us not knowing the exact arrival/departure day and was happy to shift us back or forward if the flights turned out different to what we expected. I had done as much research as possible and was fairly sure our dates would be the cheapest, so the risk was minimal for us. We chose to book flight and accommodation separately because although the all-in packages seemed appealing at first, we didn’t like not knowing exactly which villa we’d get until arrival, and I’d also read that private owners do tend to take much better care of their property than big companies do – this seems pretty obvious really! Cost-wise our option also worked out substantially cheaper, and I’m sure we got a lot more bang for our buck. 😉


Take a look at my next post in this series – You can’t do everything

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