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How to Split Rome/Tuscany with Eight Month Old

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Hi Everyone-
We are planning to do Rome and Tuscany in late September/early October with our then eight month old. I am looking for advice on how to structure our trip as I have read all the boards and the various insights on heading straight to Tuscany upon arrival or staying in Rome and then going to Tuscany and I just wanted to get input with our specific situation.
1) We have two weeks to work with including travel days.
2) Fly roundtrip Detroit-Rome nonstop, would rather not do FLR on one end due to nonstop from FCO to DTW. Have decided to omit Florence as we just want to take it slow and enjoy.
3) Do we scoop up rental car from FCO after arriving at 9:30am and head straight to Tuscany, looking at staying outside Siena OR do we do Rome and then head to Tuscany but then that would require overnighting in Rome again or at airport hotel before return flight not ideal but doable. I have read about taking train to Orievto and then picking up rental car from there, thoughts on that?
4) Any good AirBNB or apartment rentals in Rome/Tuscany? Budget would be around $300-400 per night. We have SPG and Marriott points to burn before merger ruins them but I know staying in a hotel room w/ baby is not ideal.
I appreciate your input everyone!!!

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