Toasted Oak

You might think it doesn't get much better than a swimming pool, a garden in bloom and panoramic views of the Italian countryside, but this home's heritage is what caught our eye. The villa has stood within the Montagnola nature reserve for over a thousand years, and though it has been modernised since, it has kept hold of a lot of the original charm. Surrounding apartments means it isn't always private, especially around the shared pool, but the home is a retreat for big groups and a good base when you're exploring Siena, San Gimignano, or beyond. Having breakfast included is a nice touch, especially when it's alfresco.

Home truths:
*We suggest hiring a car for ease – there's free parking here.
*You'll have access to the swimming pool and garden here. They're shared with the building's other residents.
*At full occupancy, two guests will be sleeping on the sofa bed in the living area.
*Breakfast is included here, but you'll also find restaurants and cafes 1.5km away.
*With a few other apartments around there's a chance you might see a neighbour or two, so it doesn't feel completely private.
*Events may be allowed – speak to your host.