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We always have our pool heated whenever we go to our villa. Can't stand all that dabbling your toes in business, as, like Steve, I want to get straight in and not spend hours acclimatising myself to the temperature, but then I am a wimp![msnwink]
We, like Steve, heat our pool to 88 degrees and we have good feedback from our guests about this. We don't include pool heat, guests choose whether or not to have it, but as you can see, each villa owner is different. Of course, if guests found this too warm we would turn it down.
I would suggest that when you have chosen your villa you ask the owner what temperature the pool is set to. We find 84 too cool for us, but you may find it ok. For comparison, our local swimming pool here in the UK is set to about 85 degrees and that takes me a bit of time to get into, so you could compare the temperature of your local pool and see if it is warm enough for you - if its too cold then you need a pool which is heated to a higher temperature, if it is ok then that is your baseline. But remember that the hotter the outside temperature the cooler the pool will feel in comparison, and it does get hot in Florida - hotter than at your local swimming pool.
What I can tell you is that everyone has their own idea about what constitutes a 'warm' pool! Only you know what your family like. There are wimps like me and there are hardy mortals who would swim in the pool in December without any heat, and everything in between!
However, I would definitely recommend pool heat for October. By having the pool heated and using the pool cover provided (again, check with your villa owner to make sure that they DO have a pool cover as this really does help to keep the pool warm, especially at night) you will be sure of a lovely warm pool when you return from the parks, and want a relaxing swim or just somewhere to ease those tired feet.
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Most of our guests like pool heat in the summer - its their choice, and whatever makes them happy is ok by us. As you say, we are all different, and thankfully we can all be catered for.[msnwink]