For purposes of filling out the charitable donations section of TurboTax, no, you do not need to list multiple donations to the same charity separately. It is good enough to add them all together and make a single data entry. It all flows onto Form 1040 Schedule A (charitable donations and other itemized deductions) the same.
As long as you have all of your receipts (or some other verifiable records), and can prove the donations to a hypothetical auditor, then it will not matter at all. If the program asks you for a donation date (of the multiple items), it is often a convention in tax accounting to pick the mid-year date for something like this. So, for example, you could say that you gave X number of toys to charity Z on 07-01-20YY, valued at $$$.
Thank you for asking this question.