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If you prefer mild spring weather (and it doesn't need to be HOT):
Not sure from Canada but from Europe it would be any of the Canary Islands, i.e. Gran Canaria or Tenerife. 4-5 50x50 mile islands close to Africa
Belongs to Spain, very clean, very safe, it's like being in central Europe but with better weather. Telefonica offers <50 Euro DSL there and as last resort dial-up is possible from everywhere at ~1 cent/minute, there should be also a couple WLAN hotspots
In January its 21° air 19° water, Feb should be the same or better, certainly not as warm as Cuba or Jamaica
Renting a house or big apartment right at the beach is 1500-$3000 per month
The touristic hotspots are "Playa del Ingles" in south Gran Canaria and "Las Americas" in south Tenerife
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