Re Portugal... I found myself in Albufiera for a week last autumn, slightly later than you are looking. Undoubtedly is is full of rental properties and I'm not sure which bit of town we went to a couple of times, but it was full of restaurants and bars, some of which had fairly lairy Brits (and others) in as the evening wore on. But it really wasn't so bad, if you like to see a bit of life on your holiday rather than hiding away from it all. I like both, so some some nights we went there and others we went elsewhere, or nowhere...
Better would be somewhere further along the coast - the place I know quite well is Armacao da Pera. Again, full of rental properties but quite a pleasant "prom" and some nice and reasonable eateries. Other places I looked at were Quarteria & Vilamoura (pricey) and Portamiao, and the Alporchinhos area was recommenced to us. All are by the sea.
I think the first two weeks of Sept are still within their high season so car hire etc is not so cheap, but last year the weather was glorious right through till October.
I think that Portugal would be vastly cheaper (if that's important to you) than Italy but I may be wrong.
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