Hotel Conundrum....WWYD?

If I were you, I would just stay near WDW during the entire trip. If you are a preferred member at a rental car company, you typically by-pass the counter and go straight to car, so you are not really wasting any extra time. Staying near MCO seems like you would be spending extra time going back and forth from hotel picking up and dropping off rental car then driving to/from WDW.
 
And if you are there for that short a period of time anyway, then it makes little sense to have an expensive hotel as the lodging would only be used for sleep.
 
Drive shouldn't be bad so late at night and so early in the morning. We have often gotten a driver at the airport to take us to WDW. If you go straight to a park they have lockers for backpack storage.
 

IMHO, to maximize your sleep time and park time:

1) Arrive MCO, pick up rental car. Be sure to be in rental car company program so car pick-up is quick. Pay for them to refill tank instead of you buying gas. If you are pre-registered in their program, this should be NO time at all - just the time to walk to the rental car area, pick a car from your assigned area, and a stop at the gate to check out with agent.
2) Drive to a WDW property hotel, check-in, sleep. Ideally, if you have done online check-in and given them a correct arrival time, you should be able to go directly to your room and not even have to go to the main building to "check-in" - use your MB or phone to unlock resort room door.
3) Use car to drive back and forth to all parks and your resort.
4) Drive back to airport earlier enough to catch your flight.

For a quick weekend like this, I would prioritize sleep and park time, not money.
 
Option #1 - Hotel by WDW, if not inside the WDW bubble. One that gives you Magical Express (you already have to lug your luggage to the bus). Just make sure when you do online check in, note on the reservation late arrival.

Once you deplane, collect your luggage, get to ME, get to the resort, it will likely be after midnight. You can wash up, fall into bed, and sleep. Set the alarm if you want to rope drop.

Time and convenience is also something to be valued. Look for deals at hotels at WDW (there is a Disney Visa deal going on now, as well as some early deals for stays up to March-ish).
 
I don't think a rental car is worth it for such a short trip. I would book the cheapest WDW hotel, Lyft or Uber to/from airport if you don't want to use ME.
 
IMHO, to maximize your sleep time and park time:

1) Arrive MCO, pick up rental car. Be sure to be in rental car company program so car pick-up is quick. Pay for them to refill tank instead of you buying gas. If you are pre-registered in their program, this should be NO time at all - just the time to walk to the rental car area, pick a car from your assigned area, and a stop at the gate to check out with agent.
2) Drive to a WDW property hotel, check-in, sleep. Ideally, if you have done online check-in and given them a correct arrival time, you should be able to go directly to your room and not even have to go to the main building to "check-in" - use your MB or phone to unlock resort room door.
3) Use car to drive back and forth to all parks and your resort.
4) Drive back to airport earlier enough to catch your flight.

For a quick weekend like this, I would prioritize sleep and park time, not money.
if you are staying WDW property why rent a car and not use Magical Express?
 
Time and convenience is also something to be valued. Look for deals at hotels at WDW (there is a Disney Visa deal going on now, as well as some early deals for stays up to March-ish).

Do you get Magical Express if you book a discounted rate for WDW resort through Priceline, Hotwire or Hotels Tonight?
 
Here is my advice:

(1) Stay at a WDW area hotel for, at the very least, Thursday and Friday nights. You'll be glad for the shorter commute on your park days.
(2) If you can't get the MCO Hyatt (in the airport) for a reasonable price for Saturday night, I would stay at the WDW area hotel for 3 nights. The early Sunday morning commute to MCO is quick and painless. It's less than 30 minutes from the WDW area to MCO. You really won't be saving any time by staying near the airport and the cost for renting a car for 3 nights with a Saturday night keep is the same for renting a car for 2 days with a Saturday return.
(3) DON'T use your Hilton points unless you are totally flush with them They are better used another time when prices are not so cheap. Personally, I would use Priceline to get super cheap hotels. Here is a link to one of the DIS Priceline threads: https://www.disboards.com/threads/priceline-express-deals.3598657/page-331#post-62524886 . You can also look at the Orlando board for offsite recommendations. People really like the Rosen Inn (formerly the Clarion Inn LBV) and the Red Lion.
 
Here's my two-cents worth:
Since it's such a short trip, I would stay at a WDW hotel the entire trip. Since HS is in your plans, I would recommend staying at one of the the Disney Boardwalk area resorts. This will allow you to walk to HS. This actually gives you more control over your timing to get to HS than driving. And then you can either walk or boat back to the resort if you need a break mid-day. The disney bus trip to AK is a pretty quick ride too. Then you can take DME back to the airport in the morning before your flight. This way, you won't have to worry about checking out of the Disney hotel on Saturday and having to figure out what to do with your backpacks that day.

Taking this approach will cost more in hotel expenses, but you won't have the car rental expense or the park parking expenses. You will also have the use of your room for your entire trip. No waiting for the 4pm check-in on Friday or checking out by 11am on Saturday.

This will most likely be the more expensive option, but it also maximizes your park time.

This sounds like a great trip!!!! Have a great time!!!
 
I agree about the Boardwalk area. The Swan and Dolphin are also solid choices, and cost less than the BC, YC, and Boardwalk Inn and villas. You could just Uber or Lyft to and from the airport. It is such a short trip, I’d not want to waste time moving hotels.
 
I agree about the Boardwalk area. The Swan and Dolphin are also solid choices, and cost less than the BC, YC, and Boardwalk Inn and villas. You could just Uber or Lyft to and from the airport. It is such a short trip, I’d not want to waste time moving hotels.
Problem with Swolphin is no free Magical Express
 
My suggestion is try to get a Disney Resort through Priceline, Hotels Tonight, Hotwire. Then you pay alot less and get the free Magical Express. And you can save your Hilton points for a 5 star $400 a night hotel in Europe or Asia.
 
Problem with Swolphin is no free Magical Express

It’s about a $40 Uber, so not a huge deal to me. Plus, waiting for ME sometimes is a pain. On the return flight, they allow so much time, once we did it on return, and it was an hour until we were on our way to the airport after stopping at another resort. Uber is quicker, and you can minimize your time that way.
 
In my experience, rental car is faster to and from airport than MDE. And with a 7 am flight and no luggage, I think they get more sleep time on departure day.
This person seems inexperienced and with a low budget.
I think in these cases rental cars is more costly (on top of making a mistake such as taking the toll road and racking up $$$ on the rental bill) than the free Magical Express and the stress of filling the rental car to full and making it back on time (and not getting overcharged $$$). Or getting overcharged because you are using Sixt or some no name brand.

The cost of sleep is basically free on a low budget and can be transferred to sleeping on the plane or in the airport or at home.
 












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