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Algarve is a great choice for winter. I’ve spent some time in Portimão and really enjoyed it, planning to head back this October. It’s close to beautiful cities, has nice beaches, affordable rent prices, and nice surfing spots around. It can be a touristy place, but it's pretty quiet during the off-season in late autumn and winter.

Lagos is also a very nice place, and Sagres area is great if you’re into surfing

Thank you @augis for the tip! I finally booked an Airbnb, eventually settled on Portimao to. Will be there for Jan-Feb.

That's nice, glad I could help. You'll love this place!
Now I'm in Portimao until winter, it's nice to be back here

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