Province of Siena ski-in/ski-out rentals

We found 3 ski-in/ski-out rentals — enter your dates for availability

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October 2025

November 2025

Find the best place to stay - Province of Siena

Premier Host

Ciliano 16

Sleeps 4 · 2 bedrooms · 2 bathrooms

Private and cozy retreat in Montalcino with private pool surrounded by vineyards

Sleeps 6 · 2 bedrooms · 2 bathrooms

Premier Host

Tuscan villa pool spa Siena Montepulciano Perugia Pienza Florence 2 hours from Rome

Sleeps 12 · 4 bedrooms · 2+ bathrooms

Top rated rentals - Province of Siena

Premier Host

Secret Val D’Orcia

We have stayed in the Val D’Orcia before - it’s an area we love, but this was really next level.Privacy, huge beautiful grounds and amazing views from every window!Wonderful hosts who went out of their way to make this the most special stay - thank you, it was amazing!

Vernon H.

Stayed May 2025

Premier Host

Fabulous Experience

This is a modern apartment in a peaceful authentic walled city in the heart of Tuscany- Monticchiello! It has great restaurants- Daria and La Porta to name just two. It is located close to Pienza, Montipulicano, Montalcino and the Brunello wine country. Francesco is the host and owner. He provides a wonderful breakfast and free laundry service. He is very responsive and takes great care of his guests. The four of us had a wonderful time there and highly recommend this town and property. You will not be disappointed.

John M.

Stayed Sept 2022