Make my trip cheaper!!

Your budget is great for a family of five coming in from Canada. I don't see how you could do much better.
If it really is a hardship, you should really put off the trip until you can save more. It makes no sense to be stressed about costs when we are trying to de-stress about life back home. I totally get the pull of going sooner, but I'm thinking in your case it may not be worth it.
 
I think the condo rental for Windsor Hills is high. The price you quoted you could probably get a 3 bedroom townhouse at Windsor Hills. Also make sure you request an Orlando Magic card, there are some great deals in the brochure for Canadians. If you are looking for an interesting side trip for a morning or afternoon the Orlando Science Center is cool for children under 10. They even have an indoor aquatic area where you can get up close to stingrays and alligators. They have excellent interactive exhibits and a planetarium. When we went Canadians got 50 off we the magic card. It was well worth the time. Also we stop in Georgia to buy our groceries which I find much cheaper than Florida. Meat is half the cost as florida. We have a electric cooler in our car.
 
You could stay at Fort Wilderness for $50 - $60 a night and be on Disney property eliminating the parking fee.

We camp at Disney. See my trip report on how we lived in tents for 3 weeks.

Best time ever!
 
My tip is to decide on your condo meals ahead of time, or at least have a rough idea of what you'll be making. Bring little baggies/packets with all the spices or spice mixes you'll need. All those little bits don't take up much room in the car, but they save you a lot on buying a whole jar of oregano, chile powder, etc when you get there.

Good call on all fronts and i'll be sure to include ketchup and all other assorted condiments.

It makes no sense to be stressed about costs when we are trying to de-stress about life back home.

Agreed.

The price you quoted you could probably get a 3 bedroom townhouse at Windsor Hills.

Any chance you could hook me up with a link in the right direction for said townhouse?

We camp at Disney. See my trip report on how we lived in tents for 3 weeks.

First off I can never turn down a trip report :). Secondly i'm intrigued. My family loves camping but i'm not so sure about camping in Florida Heat. That being said May is actually the equivalent of the kind of temperatures we get in Ottawa during summer so while September is certainly out we could definitively consider it for May... this will require more looking into. thanks.
 

Any chance you could hook me up with a link in the right direction for said townhouse?
You can google "windsor hills rentals" and that should bring up a website where owners put their condos and townhouses up for rent. You can enter a request for your dates and the owners will get back to you with their rates.

I booked at Windsor Hills through http://www.vacationcentralflorida.com/ but they only book Sat-Sat so even if that works for you, you may have to book a single night somewhere else for your 8th night.
 












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