WWYD - offsite or a value

I'd stay offsite. It fits your budget the best. If you have to check out by 11am and your room at SSR isn't ready early, throw everything into the car and have a leisurely lunch at Disney Springs or one of the resort hotels. Eat, roam, shop... and your room will be ready for you to check in!

That’s exactly what I was thinking, except we will not have a car!

My plan, head to SSR right after checkout at hotel #1, drop our bags off with luggage services, and enjoy the pool and grab something to eat. Sounds perfect to me! Oh as an aside, we’ll each purchase a refillable mug since we plan on spending a fair amount of time at the resort.
 
That’s exactly what I was thinking, except we will not have a car!

My plan, head to SSR right after checkout at hotel #1, drop our bags off with luggage services, and enjoy the pool and grab something to eat. Sounds perfect to me! Oh as an aside, we’ll each purchase a refillable mug since we plan on spending a fair amount of time at the resort.
So I'm not sure which hotel you have booked that first night, be aware that it's a nice walk over to SSR, but it's pretty far. Esp. over to the checkin lobby.... I was gonna say it depends on if you have a rental car or not. Since you don't, You have to calculate the distance in heat etc,(I think it's at least a mile or so by the time you get all the way to checkin from even the closest hotel on that road) So if cost is equal, I'd vote for a cheap all star hotel first night. That way it's easier to get your ride there, then let Disney transfer luggage to SSR the next day. (I'm a fan of the hotels along that road btw, but in this case I vote value)
 
There's uber and such too to get between whatever hotel is selected. I'm not sure if the price that would be charged would differ between being completely on Disney's property but the off site hotel was closer in proximity to SSR theoretically it would cost less (outside of surge pricing).
 
I kind of did the opposite of this transfer earlier in the year. Stayed at the Wyndham right near Disney Springs, but used a bus to Sarasota + a walk to get back to my hotel at night. It was the first time I've ever actually enjoyed being in Disney Springs. You could walk to DS from your first hotel and then ride a boat to SS to fill time and save some walking.
 

@hsmamato2 and @Mackenzie Click-Mickelson we plan on taking an Uber or Lyft from our offsite hotel to SSR. Right now, I have the Holiday Inn booked. With resort fee and taxes, it’ll be approximately $200 USD (with resort fee and taxes) for the night, which meets my budget.
it's a nice hotel you'll like it fine- free coffee in the lobby every morning (and tea) and free afternoon cookies and lemonade
 
Airport Hyatt. Getting in that late, you can settle right in and get an early start next morning. You can also arrange your ground transportation right there. Mears or Uber the next morning, or you would save a days cost of a rental car. Also allows for a minimum luggage movement.
 





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