Pienza Winter Rentals & Holiday Homes
Discover winter rentals Pienza - We found 65 exact matches
When do you want to travel?
- Air Conditioner
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- Pet Friendly
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- TV
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- Pool
- Private Pool
- Air Conditioner
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- Private Pool
- Air Conditioner
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- Air Conditioner
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- Pet Friendly
- Air Conditioner
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- Pet Friendly
- Air Conditioner
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- Pool
- Air Conditioner
- Pool
- TV
- Air Conditioner
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- Pet Friendly
- Air Conditioner
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- Pool
- Air Conditioner
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- Pet Friendly
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
- Pet Friendly
- Pool
- TV
- Air Conditioner
- Parking
- Pool
- Parking
- Pet Friendly
- Pool
- Air Conditioner
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- Pet Friendly
Frequently Asked Questions About Pienza Winter Rental
What are the top rated Winter Rentals in Pienza?
There are a lot of options in Pienza. If you plan on staying in the Pienza area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Pienza:
- Villa Fontana
- Pienza villa rental with pool
- Villa Le Fontanelle by Fantasia Villas
- Large Tuscany Villa rental near Pienza - southern Tuscany
- Villa Irmina: A characteristic and welcoming two-story ancient tuscan country house surrounded by meadows and by green hills, with Free WI-FI.
- FONTE ALL'OPPIO - FONTE ALL OPPIO
- Villa delle Fontane Amazing place for your holiday
- Affittacamere Maria Gabriella, B&B and Holiday Home in Val d'Orcia
- PODERE ISABELLA - podere isabella
- Villa Suriana: A charming two-story age-old farm house surrounded by meadows and by green hills, with Free WI-FI.
How much does it cost to rent a place to stay near Pienza in the wintertime?
The average cost for winter rentals in Pienza is $1,142 per night. Cottageromance has a wide list of great winter places to stay near Pienza that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Pienza that allow pets?
Yes, here are the top cottage/chalet rentals in Pienza that allow you to bring your pet or dog:
- Villa I Cipressini piscina riscaldata spa Toscana
- Villa Arpicella Pienza Siena Italy Tuscany, a stunning, green, peacefull corner
- La CoCCa Luxury Villa in Monticchiello, your heaven in Tuscany
- Wonderful villa for 8 people with private pool, WIFI, TV and panoramic view, close to Montepulc.
See all pet-friendly vacation rentals in Pienza on Cottageromance
Do you have any winter rentals in Pienza that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Pienza to find what works for you.
Are there winter accommodations in Pienza that have indoor swimming pools?
As of 2026, the data from Cottageromance shows that there are over 65 private swimming pools or indoor pools accommodations near Pienza along with other great amenities.