City Mini GT2 Single Stroller
All-terrain tires and a hand brake — the upgrade pick for long park days.
from $70 / 3 days
See details and datesVacation home delivery
Stroller rental at Windsor Hills Resort
Best Stroller Rental delivers strollers and car seats to Windsor Hills villas and townhouses from $60 for three days. It is about two miles from the Western Way entrance to Walt Disney World, and almost every family drives. Give us the house number and gate instructions at booking, and a City Mini fits a rental SUV boot.
Part of our Kissimmee stroller rental coverage.
How does delivery work at Windsor Hills?
Windsor Hills is the closest large vacation-home community to Walt Disney World — about two miles from the Western Way entrance — and almost every family here drives. That combination means two things: you need a car seat, and you need a stroller that fits in a rental SUV boot alongside the luggage.
We deliver to the door of your villa or townhouse. Give us the house number and gate instructions at booking; if you are arriving late we can leave gear with the management office or in a garage if you arrange access.
Because the community is gated, we ask for the gate code or your rental company's name so the driver is not stuck at the barrier with your stroller.
What should you know about Windsor Hills?
- Windsor Hills is roughly a 10-minute drive to the Disney gates and 20 to Universal.
- Most homes here sleep 8 to 12, so double strollers and second car seats are common bookings.
- The community's internal paths and clubhouse area are flat and pushable for evening walks.
How long do families rent a stroller for Windsor Hills?
Seven to fourteen days. Vacation-home stays are the longest rentals we do, and ten days or more triggers our lowest daily rate and free delivery.
Every rate is priced by trip length — see the full stroller rental pricing table.
Which stroller or car seat should you rent for Windsor Hills?
OneFit ClearTex All-in-One Car Seat
Rear-facing, forward-facing and booster in one seat — 5 lb to 120 lb.
from $50 / 7 days flat
+ $5 per extra day
See details and dates
City Mini GT2 Double Stroller
The double that pushes like a single. Our most-requested gear in peak season.
from $90 / 1–3 days
+ $5 per extra day
See details and datesSee every option on our Orlando stroller rental and Orlando car seat rental pages.
Windsor Hills stroller rental questions
Do you deliver inside the Windsor Hills gate?
Yes, to the villa door. Give us the gate code or the management company name when you book.
Can you deliver before we arrive?
Yes, if the property manager gives access. Otherwise we schedule around your arrival time.
Do we need a car seat at Windsor Hills?
Almost certainly. There is no resort transport, so families drive, and Florida law requires a restraint for children under six.
How much does stroller delivery to Windsor Hills cost?
Delivery is $10 each way in Kissimmee, waived on rentals of ten days or longer.
Related pages
Gear waiting when you land
Pick your gear, pick your dates, tell us where you are staying. We deliver clean, inspected equipment and collect it when you leave.