Is it possible to have late check-out?
'late' is pronounced approximately as in English — IT-alians borrow the word.
Ask the evening before departure or at least the morning before. Availability depends on that day's arrivals.
'È possibile' (is it possible) + infinitive is the Italian equivalent of 'can I' in polite requests. It is slightly more formal than 'posso'. The anglicism 'late check-out' is universally understood in Italian hotels. Grammatically it is treated as a masculine noun.
Posso restare in camera fino alle quattordici?
Can I stay in the room until two?
Specify the exact time you need rather than just asking vaguely
Il late check-out ha un costo?
Does late check-out have a cost?
Ask before assuming it is free — policies vary
C'è disponibilità per un late check-out domani?
Is there availability for late check-out tomorrow?
Asking the night before gives the hotel time to check
Late check-out availability in Italian hotels depends entirely on the day's incoming bookings. In low season, it may be free. In peak summer, even paying will not guarantee it. Ask the evening before and be flexible — the hotel cannot hold a room indefinitely.