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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 31 to 60 of 65 villas
Save $256 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,513/wk
  • max $2,561/wk
  • min $1,362/wk
  • max $2,305/wk
  • Min Stay: 5 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $256 when you book by Oct-20-2018**
" This property is excellent. The owners are the most wonderful people. They were always gracious, helpful and friendly. We had a two bedroom apartment with a rea..." - Julie
Save $367 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $2,057/wk
  • max $3,665/wk
  • min $1,851/wk
  • max $3,299/wk
  • Min Stay: 5 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $367 when you book by Oct-20-2018**
" Our overall experience was fantastic. We were a group of 6 adults, retirement-aged, and were overwhelmed by the property. It fitted our needs beautifully. It wa..." - Nanci
Save $318 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,784/wk
  • max $3,184/wk
  • min $1,606/wk
  • max $2,866/wk
  • Min Stay: 5 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $318 when you book by Oct-20-2018**
" We four girls absolutely LOVED it! It was what I imagined. The owners are VERY dedicated!..." - Lynn
Save $938 Photo of Beautiful Farmhouse in the Chianti Near Town
  • min $5,528/wk
  • max $9,380/wk
  • min $4,975/wk
  • max $8,442/wk
  • Min Stay: 7 days
Sleeps 9 people
  • 1 single bedrooms
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $938 when you book by Oct-20-2018**
" We had a wonderful, peaceful time...." - Davis
Save $335 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,945/wk
  • max $3,346/wk
  • min $1,751/wk
  • max $3,011/wk
  • Min Stay: 5 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $335 when you book by Oct-20-2018**
" Enjoyed my stay at the villa. Management ia very friendly and helpful...." - Sharon
Save $925 Photo of Farmhouse Rental in Tuscany, Gaiole in Chianti (Chianti Area)
  • min $8,111/wk
  • max $9,245/wk
  • min $7,300/wk
  • max $8,321/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $925 when you book by Oct-20-2018**
" We took this trip to celebrate our 40th anniversary. We were joined by our three adult children and their significant others and our grandson. We had a wonderful..." - Mark
Save $268 Photo of Hilltop House in Tuscany
  • min $1,786/wk
  • max $2,679/wk
  • min $1,607/wk
  • max $2,411/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $268 when you book by Oct-20-2018**
Save $613 Photo of Elegant San Gimignano Villa with Pool near historical sites, art museums.
  • min $3,890/wk
  • max $6,125/wk
  • min $3,501/wk
  • max $5,513/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $613 when you book by Oct-20-2018**
Save $252 Photo of Restored Farmhouse Surrounded by Vineyards and Olive Groves, Centrally Located in Tuscany
  • min $1,762/wk
  • max $2,521/wk
  • min $1,586/wk
  • max $2,269/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $252 when you book by Oct-20-2018**
" Great. Claudia and Rudi terrific ..." - Frank
Save $181 Photo of Vacation Rental Agritourism in Tuscany
  • min $1,520/wk
  • max $1,814/wk
  • min $1,368/wk
  • max $1,633/wk
  • Min Stay: 4 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $181 when you book by Oct-20-2018**
" Beautiful property, apartment well-appointed. Claudia and Rudi very friendly and helpful finding local eateries, grocery stores. Very quiet and although we were ..." - Susan
  • min $2,352/wk
  • max $4,587/wk
  • Min Stay: 3 days
Sleeps 5 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Very good to excellent. The manager was very good... location was amazing, apartment was very comfortable. ..." - Mar
Save $1,260 Photo of Beautiful Chianti Villa with Guest Cottage and Private Infinity Pool
  • min $9,522/wk
  • max $12,602/wk
  • min $8,570/wk
  • max $11,342/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,260 when you book by Oct-20-2018**
" It was fantastic. ..." - Jessica
Save $118 Photo of Tuscany Holiday Apartment
  • min $932/wk
  • max $1,177/wk
  • min $839/wk
  • max $1,059/wk
  • Min Stay: 4 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $118 when you book by Oct-20-2018**
" Absolutely wonderful. Experience enhanced by the warm hospitality of Claudia and Rudy - we left feeling like family friends not hospitality guests...." - Kay
Save $370 Photo of Villa Rental in Tuscany, Castellina in Chianti (Chianti Area)
  • min $938/wk
  • max $3,697/wk
  • min $844/wk
  • max $3,327/wk
  • Min Stay: 7 days
Sleeps 8 to 10 people
  • 4 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $370 when you book by Oct-20-2018**
Save $1,285 Photo of Large Chianti Classico Villa with Swimming Pool and Spa near Siena
  • min $11,611/wk
  • max $12,850/wk
  • min $10,450/wk
  • max $11,565/wk
  • Min Stay: 3 days
Sleeps 18 people
  • 9 double bedrooms
  • 10 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,285 when you book by Oct-20-2018**
Save $967 Photo of Large Farmhouse on a Wine Estate near Siena Fit for Families
  • min $5,511/wk
  • max $9,665/wk
  • min $4,960/wk
  • max $8,699/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $967 when you book by Oct-20-2018**
" Villa Castellina is unbelievably wonderful. It went beyond my wildest imagination. The views were spectacular, modern, comfortable. All of us were so pleased, e..." - Pamela T
Save $829 Photo of Farmhouse in the Chianti Region for Friends or a Large Family
  • min $4,138/wk
  • max $8,292/wk
  • min $3,724/wk
  • max $7,463/wk
  • Min Stay: 7 days
Sleeps 11 people
  • 1 single bedrooms
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $829 when you book by Oct-20-2018**
" Terrific! Everything worked, the villa was comfortable and very clean, and it was wonderful to be out in the countryside and simultaneously next to a substantiall..." - Alexander
Save $309 Photo of Family-Friendly Apartment Close to Siena
  • min $1,539/wk
  • max $3,088/wk
  • min $1,385/wk
  • max $2,779/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $309 when you book by Oct-20-2018**
" The size of the bedrooms, bathrooms and the outside patio area...." - Monica
Save $265 Photo of Family-Friendly Apartment Close to Siena
  • min $1,382/wk
  • max $2,645/wk
  • min $1,244/wk
  • max $2,381/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $265 when you book by Oct-20-2018**
" Very good. We were upgraded us to a larger unit...." - Donna
  • $915/wk
  • $824/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Washing Machine
** Save up to $92 when you book by Oct-20-2018**
" The location was perfect, both in relation to the town, and to the parking...." - Christine
Save $210 Photo of Apartment for a Family in the Center of Siena
  • min $1,680/wk
  • max $2,100/wk
  • min $1,512/wk
  • max $1,890/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $210 when you book by Oct-20-2018**
Save $719 Photo of Tuscany Holiday Villa
  • min $5,951/wk
  • max $7,186/wk
  • min $5,356/wk
  • max $6,467/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $719 when you book by Oct-20-2018**
" We had a wonderful experience at this property. It was a perfect location close to Siena. ..." - Pennie
Save $216 Photo of Family-Friendly Apartment Close to Siena
  • min $1,079/wk
  • max $2,162/wk
  • min $971/wk
  • max $1,946/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $216 when you book by Oct-20-2018**
" Overall the property and atmosphere were great. The location was convenient to Siena and we found this to be very enjoyable, much more so than Florence...." - Peter
Save $1,365 Photo of Villa Rental in Tuscany, Gaiole in Chianti (Chianti Area)
  • min $7,525/wk
  • max $13,650/wk
  • min $6,773/wk
  • max $12,285/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,365 when you book by Oct-20-2018**
Save $123 Photo of Tuscany Vacation Rental Agritourism
  • 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**
" This was my second visit in five months! I love it!..." - Barbara
Save $137 Photo of Holiday Apartment in the Center of San Gimignano
  • $1,371/wk
  • $1,234/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Washing Machine
** Save up to $137 when you book by Oct-20-2018**
" This property is well situated and is quite comfortable for 2 couples...." - Sonia
  • $915/wk
  • $824/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Washing Machine
** Save up to $92 when you book by Oct-20-2018**
" the apartment was as advertised and quite comfortable for our needs. It is well situated on the edge of the wall to make parking more convenient and only a couple..." - Linda
Save $137 Photo of Holiday Apartment in the Center of San Gimignano
  • $1,371/wk
  • $1,234/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Washing Machine
** Save up to $137 when you book by Oct-20-2018**
Save $1,094 Photo of Beautiful Historic Villa Near Monteriggioni in Tuscany
  • min $8,629/wk
  • max $10,935/wk
  • min $7,766/wk
  • max $9,842/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,094 when you book by Oct-20-2018**
" I would and already have recommended the villa to anyone. My experience with your firm was excellent. When I return to Tuscany I intend to stay at the same locatio..." - Hal
Save $521 Photo of Apartment Rental in Tuscany, Monteriggioni
  • min $3,720/wk
  • max $5,208/wk
  • min $3,348/wk
  • max $4,687/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Washing Machine
  • Maid Service
** Save up to $521 when you book by Oct-20-2018**
" It was great..." - Barbara
 
Displaying 31 to 60 of 65 villas

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..