Hi Todd! Walt Disney World Resort offers stroller rentals for single day and multi-day usage at several locations throughout the Theme Parks, the Water Parks and Downtown Disney Area.
The stroller rental fee is $15.00 USD per day for a single-passenger stroller and $31.00 USD per day for a double-passenger stroller. A $100 USD credit card deposit is required per strollers rented at the Downtown Disney Area. The rented stroller must be returned to the original rental location to receive a credit card deposit refund.
For Guests who require a stroller rental for multiple days, a length of stay rental ticket where you make a one-time payment transaction for as many days of rental as you will need is offered. Upon visiting a Disney Theme Park, a Water Park or Downtown Disney Area, show your receipt at the stroller rental location and you will be expedited through the queue with a reduced wait time. The multiple day rental fee is $13.00 USD per day for a single-passenger stroller and $27.00 USD per day for a double-passenger stroller.
Todd, I could not find any information on multiple stroller rental discounts. I would recommend that you plan for the cost of the stroller rental as listed above, but ask the Cast Member upon your arrival to Walt Disney World Resort about a discount. It never hurts to ask. Hope this helps!