Cortona Winter Rentals & Holiday Homes

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

• Tuscan Villa private infinity pool, exclusive location, AC, extra services
• Luxury Cortona view hilltop Villa
• Beautiful villa for 6 people with pool, WIFI, A/C, TV and panoramic view
• Villa Mulinoavento with magnificent view 5 minutes walking downtown
• Casa Ivan - Apartment with swimming pool
• Villa Ai Cedri Cortona
• Beautiful private villa with WIFI, private pool, A/C, TV, patio, pets allowed and panoramic view
• Villa in Il Castagno with 3 bedrooms sleeps 8
• Historic 14th Century Church Villa with Private Pool in vineyard near Cortona
• Elegant & Comfortable Tuscany Farmhouse Villa in Cortona Italy

The average cost for winter rentals in Cortona is $704 per night. Cottageromance has a wide list of great winter places to stay near Cortona 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 Cortona that allow you to bring your pet or dog:

• "Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
• Villa at 300 m altitude with private swimming pool and views of Cortona
• Pierle Cuiano Villa: Mountain Views, Private Pool & Wi-Fi in Agriturismo
• Stunning Private House: fantastic pool, beautiful views, A/C, Wi-Fi, and privacy

See all pet-friendly vacation rentals in Cortona on Cottageromance

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

As of 2026, the data from Cottageromance shows that there are over 410 private swimming pools or indoor pools accommodations near Cortona along with other great amenities.