At the top of a ridge, a sea of hills awaited, their green waves rippling towards the horizon. I had arrived at Ghizzano, a town in central Tuscany with just 350 residents. My home town.

Said to have been designed by Michelangelo himself, above, Villa Machiavelli is a piece of history nestled among Tuscany’s rolling hills—and now it can be rented. Getty Images Home to the ...