Dear all,
You are going to need an inside swimming pool, which is not common in Greece. I would doubt that you would find that on Santorini.
Go somewhere like Tenerife and you can swim in the sea then.
To be honest, you are not very realistic. Only a few very up-class pricey hotels offer heated inside pools , let alone with sea view and let alone on the even more pricey Cyclades.
The few heated pool are on hotels on locations with longer season aka expensive Mykonos and Santorini. On other locations hotels might be closed by then anyway.
Some smaller, more reasonably priced hotels, might advertise one, but in reality will be no more than a small tube on room temperature,not a proper swimming pool. In deed even luxury hotels on Cyclades tend to be small-ish boutique-ish and might not have swimming pools big enough to swim proper runs...
AFRODITI VENUS on Kamari might be a compromise for your budget, singles ~ 75 euro on end October, small inside pool no sea views though and Kamari dead quite by then.
An easy filtered search on booking.com will prove what I'm saying.
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