I bought a $20 umbrella stroller for DDs first trip to disney when she was 18 months old. SHe is now five and we will be bringing it with us on our trip this August (mostly for late nights). It has been a great investment for us!
We're going with my whole family in October which includes my 2 year old DD and my 1 year old neice. We finally decided to buy a double umbrella stroller. I can't remember how much a double stroller cost to rent at Disney per day but I think we're actually saving money. Plus, we'll be off site one day so we'll have the stroller for that and for DTD where I don't think they rent strollers . Of course, my sister might be giving me another neice or nephew in the not so distant future so she can use the stroller then.
Our DDIL purchased one of those three wheeled strollers, used it for a weekend, and realized that if she took that stroller, she would have to lug it on and off the buses all day long and it wasn't light. She took it back for a sturdy but easy to manage umbrella stroller.
We would take an umbrella stroller that was lightweight and easy to carry. I think even the expensive ones at Disney would be cheaper than renting one for 8 days there.
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