Ever dreamed of spending the winter abroad? It may take some planning, but it can be a wonderful experience.  The easiest sun destinations to relocate to are the southern U.S., Mexico and the Caribbean. The number of services available and options for rental properties are plentiful. That being said some less developed countries in South East Asia like Thailand and Vietnam are great places for a long cheap holiday. I have cousins who relocate to South Africa every winter. With the exception of transport, South Africa can be quite affordable. One needs a car to get around in a place like Cape Town or stamina for still developing public transit but you can eat and drink incredibly well there at very affordable prices. Plus, outdoor activities like hiking are free and there are plenty of places to do them.

The longer you go the cheaper it tends to be for both a hotel and a rental, whether a condo, apartment or house. A long stay in a hotel is technically possible but often not practical. Many hotels have spikes in their business which makes it hard to confirm one rate over a long duration. As well, not having a kitchen or laundry facilities for a long stay makes it inconvenient. The services at a hotel all cost extra and can add up

A long term rental where you really start to get aggressive discounts is typically 6 months. A short term rental of a month or two is a more common request. With a short term rental, you can usually expect multiple bedrooms and bathrooms, a full kitchen, a patio and backyard, and hopefully some extras like a private swimming pool or even golf club membership at the local club. Prices vary widely. Make sure to ask what's included; internet, a cable package for the TV, is there a limit on air conditioning or heat, access to the local community centre, etc.  Florida and Arizona are probably the two most popular places for Canadians in the U.S. I found a two-bedroom house outside of Tucson for $750 a week in the high season. Discounts kick in for monthly rentals.

Check out www.homeaway.ca or www.vrbo.com.  They are well reputed vacation rental sites, which offer basic security features. They'll conduct background and address checks, certify hosts with a proven track record, host community discussions, and post uncensored reviews. Many also have internal security systems that flag suspect activity, which will remove shady postings and bar questionable parties from the site. As an added measure to deter cons, the peer-to-peer rental site www.roomorama.com has set up its own payment system that won't release funds to property owners until after guests successfully check in.

Before you put down a deposit, or fork over any other type of payment, make sure to get a contract that spells out the mutually agreed upon terms of service: the dates of arrival and departure, the method and timing of payments, the cancellation policy, and any additional forthcoming charges: pet, pool-heating, or cleaning fees, and hotel occupancy taxes, to name a few.

Once the practicalities are out of the way, enjoy the experience; volunteer, join clubs or take a language or cooking class and meet the locals.