You're going to love it here! Compared to CA, you will notice the humidity level in May and there may be a few afternoon showers or thunderstorms. May is kind of transitional and we start to plan more outdoor activity in the mornings, but you could just as easily hit a stretch of wonderful weather.
You will have no trouble getting to pickle ball courts by golf cart - they are at all the neighborhood rec centers. Tee times are plentiful. But check the location of the courses in relation to where you are staying - some can end up being quite a drive.
Travel to the squares and/or shopping also depend on where you are staying. In all probability, you will be within a 15 minute golf cart ride from one of the three squares. And exploring in the golf cart is half the fun. Keep in mind that most golf carts travel between 16-20 miles per hour - they are not the weaklings that you are used to renting on your local golf courses.
If your rental comes with a cart, find out whether there are side curtains to protect you from any unforeseen rain storms. However, golf carts offer absolutely no protection from lightening, and most of us have a car for back up.
As far as the rental car goes, I would keep an eye on Accuweather.com or something similar. If the weather forecast includes the possibility of afternoon thunderstorms, it might be prudent to rent a car at the airport and drive up instead of taking the shuttle. Exploring The Villages by golf cart is really a lot of fun, but that way you'll have a car for back up if you need it.
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