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You need at least platinum elite to get 4pm checkout, and even then, it's still subject to availability.
Chief
It’s actually a guarantee except at resorts, convention centers, and design hotels so not subject to availability.
You can see if your hotel is a resort in the directory by filtering on hotel type - https://www.marriott.com/hotel-search.mi
4pm not 5
Are there any restrictions on which specific properties allow it?
I’ve been denied 4 PM when I requested it at check in at the Courtyard in Omaha - was told 2 PM was the latest they could do
Chief
If your platinum or higher it’s guaranteed and you should point them to the T&Cs. If your Gold or lower, it’s based on avalobiltiy.
I have never gotten a 4 pm checkout requesr declined FWIW
You always have the privilege - be polite and friendly, ask at the right time (ie not when the lobby is packed etc), and if you’re charming enough I’ve never had them say no
Haha no