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North Siena Villas and Vacation Rentals

North of Siena lies the Chianti, Italy's definitive wine-growing region. This area boasts hills covered in vineyards, winding roads (favored by sporty drivers and daredevil cyclists), and breathtaking vistas.   Continue >

Displaying 61 to 90 of 65 villas
Save $670 Photo of Farmhouse Rental in Chianti Area of Tuscany
  • min $2,914/wk
  • max $6,698/wk
  • min $2,623/wk
  • max $6,028/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $670 when you book by Oct-20-2018**
" We were two couples and two adult singles. We booked this villa because our group was originally ten, but ended up as only six. As a result, the house was much lar..." - Mary
Save $2,002 Photo of Villa Rental in Tuscany, Castellina in Chianti (Chianti Area)
  • $20,020/wk
  • $18,018/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $2,002 when you book by Oct-20-2018**
Save $123 Photo of Farmhouse Accommodation in Tuscany
  • min $961/wk
  • max $1,230/wk
  • min $865/wk
  • max $1,107/wk
  • Min Stay: 4 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $123 when you book by Oct-20-2018**
" Beautiful stay...." - Joan
Save $160 Photo of Historic Apartment for a Couple in the Center of Siena
  • min $1,277/wk
  • max $1,596/wk
  • min $1,149/wk
  • max $1,436/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $160 when you book by Oct-20-2018**
Save $205 Photo of Farmhouse Rental in Tuscany, San Giovanni
  • min $971/wk
  • max $2,049/wk
  • min $874/wk
  • max $1,844/wk
  • Min Stay: 7 days
Sleeps 2 to 6 people
  • 1 double bedrooms
  • 1 bathrooms
  • Independent House
  • Washing Machine
  • Air Conditioning
** Save up to $205 when you book by Oct-20-2018**
 
Displaying 61 to 90 of 65 villas

Show all 108 Villas and Houses for Rent in Siena

Following the old Chiantigiana road from your Chianti vacation rental you see the heart of this region, including the Chianti Classico, the Sienese Chianti, and southeast of Siena, the border of Valdarno. To the north lies San Casciano, and further north still, Florence. What to do while staying in one of our villas in Chianti? Eat, drink, and be merry. Towns like Panzano, Greve-in-Chianti, and Radda-in-Chianti---and all the wineries in between---are filled with gastronomic delights and a dizzying selection of wine shops. View our Rental Villas in North Siena..