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Family holiday with two toddlers in October

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My son and daughter-in-law (self employed) unexpectedly find themselves with two weeks holiday, starting October 17. They have two young (3 and 18 months) old boys which makes selecting a place to stay a bit more of a 'challenge'.

They would like to stay in or very near a small town in a child friendly accommodation. Easy airport connections and a beach, if possible a swimming pool are on their wish list.

In my experience it can already be pretty rainy in Southern Spain around that time of year but I'm not sure about e.g. Sicily, Italy. I also have the experience that often many restaurants in sea-side towns are closed for the season.

Any advice or suggestions about Southern European destinations that fall into this category are most welcome.

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