Siena Winter Rentals & Holiday Homes

There are a lot of options in Siena. If you plan on staying in the Siena area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Siena:

• Typical Tuscan house.Great view on Lucca.Private parking/garden.WIFI
• Single-level Villa, panoramic position, AC, 6x16m private Pool, Whirlpool & Spa
• Antica fattoria 25 km a Siena di fronte a Montalcino con piscina/lezione di cucina
• Agriturismo Humile
• Panoramic and Charming Villa with Private Garden in Tuscany
• Casa Fantone. Villa with private pool and large fenced park for absolute privacy
• ALL PROPERTY 7BR- Charming Tuscan Villa with pool, hot tub, A/C,Siena 15 km
• VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN-SUITE BEDROOMS, SWIMMING POOL, SPA, SAUNA.
• Tuscan villa pool spa Siena Montepulciano Perugia Pienza Florence 2 hours from Rome
• Gorgeous view on vineyards, Stone Tuscan private Villa

The average cost for winter rentals in Siena is $574 per night. Byownertravel has a wide list of great winter places to stay near Siena that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.

Yes, here are the top cottage/chalet rentals in Siena that allow you to bring your pet or dog:

• House with swimming pool. Medieval village in the heart of Chianti Classico
• Villa Chiara
• Relais Val d'Orcia
• San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view

See all pet-friendly vacation rentals in Siena on Byownertravel

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Siena to find what works for you.

As of 2026, the data from Byownertravel shows that there are over 6857 private swimming pools or indoor pools accommodations near Siena along with other great amenities.