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First timer

I am hoping to stay 2 weeks at a hotel in Aruba. If the hotel I choose only has 7 day stays, has anyone ever rented 2 different timeshares back to back at the same location? Did it go smoothly? I pretty much go with the flow but I will have my elderly mother and aunt with me and I'd like things to seem very easy for them. How do the hotels usually accomodate these requests? Thank you for any advice you have!