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Chianti Villa Rentals Tuscany, Italy

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 1 to 30 of 64 villas
Save $930 Photo of Villa on Large Estate Near San Gimignano
  • min $5,300/wk
  • max $9,300/wk
  • min $4,770/wk
  • max $8,370/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $930 when you book by Sep-30-2018**
" Amazing. Pool was great for hot days and the view was priceless. Beautiful garden and very well kept. Loved coming back to the villa after a long day. ..." - Artur
Save $560 Photo of Apartment Farmhouse in Tuscany
  • 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 $560 when you book by Sep-30-2018**
" Fantastic!!! This was our 4th time to return! Loved it and love Claudia, Rudi and Simone!..." - Dana
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 Sep-30-2018**
" Great. Claudia and Rudi terrific ..." - Frank
Save $188 Photo of Country Villa in heart of Chianti centrally located close to regions’ history, art, restaurants.
  • min $840/wk
  • max $1,881/wk
  • min $756/wk
  • max $1,693/wk
  • Min Stay: 7 days
Sleeps 3 to 5 people
  • 1 single bedrooms
  • 1 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $188 when you book by Sep-30-2018**
" The property manager was a gem. The garden was so wonderful. Very inviting place and it was so convenient to go to Siena and so many wineries. One of the best v..." - Harold
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 10 people
  • 5 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $670 when you book by Sep-30-2018**
" We had a wonderful time at Villa Adelina. The rooms were large and we thought it was great that everyone had their own bathroom. I don't know how it compares..." - Patricia
Save $340 Photo of Apartment in Siena Overlooking the Famous Piazza del Campo
  • min $2,087/wk
  • max $3,399/wk
  • min $1,878/wk
  • max $3,059/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
** Save up to $340 when you book by Sep-30-2018**
" Very good...." - Kenneth
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 Sep-30-2018**
" Absolutely wonderful. Experience enhanced by the warm hospitality of Claudia and Rudy - we left feeling like family friends not hospitality guests...." - Kay
Save $560 Photo of Charming Villa with Pool in Tuscany
  • min $3,641/wk
  • max $5,601/wk
  • min $3,277/wk
  • max $5,041/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $560 when you book by Sep-30-2018**
" Very Good. A little too far from grocery store and Florence...." - Mary
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 Sep-30-2018**
" It was fantastic. ..." - Jessica
Save $406 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $1,871/wk
  • max $4,061/wk
  • min $1,684/wk
  • max $3,655/wk
  • Min Stay: 7 days
Sleeps 9 people
  • 1 single bedrooms
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $406 when you book by Sep-30-2018**
" Very nice and restful. S..." - Olenka
Save $459 Photo of Apartment Rental in the Center of Siena
  • min $2,352/wk
  • max $4,587/wk
  • min $2,117/wk
  • max $4,128/wk
  • Min Stay: 3 days
Sleeps 5 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $459 when you book by Sep-30-2018**
" Very good to excellent. The manager was very good... location was amazing, apartment was very comfortable. ..." - Mar
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 Sep-30-2018**
Save $490 Photo of Chianti Tuscany Villa Rental, Near Siena
  • min $3,186/wk
  • max $4,901/wk
  • min $2,867/wk
  • max $4,411/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $490 when you book by Sep-30-2018**
" We had a wonderful time at the property..." - Leo
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 Sep-30-2018**
" 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 $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 Sep-30-2018**
Save $299 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $1,374/wk
  • max $2,987/wk
  • min $1,237/wk
  • max $2,688/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $299 when you book by Sep-30-2018**
" Rosalia 3 is an excellent property if you are looking to spend an authentic week in the Tuscan countryside. Located in a very private setting on a wine estate, th..." - Lisa
  • $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 Sep-30-2018**
" The location was perfect, both in relation to the town, and to the parking...." - Christine
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 Sep-30-2018**
" 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 $1,094 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 Sep-30-2018**
" 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 $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 Sep-30-2018**
" Beautiful stay...." - Joan
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 Sep-30-2018**
" This was my second visit in five months! I love it!..." - Barbara
Save $260 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $1,200/wk
  • max $2,602/wk
  • min $1,080/wk
  • max $2,342/wk
  • Min Stay: 7 days
Sleeps 7 people
  • 1 single bedrooms
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $260 when you book by Sep-30-2018**
" Overall, we absolutely loved our stay at this property. It was beautiful, quiet, close to many things that we wanted to see, and a perfect mix of relaxation and b..." - Lisa
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 Sep-30-2018**
" 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 $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 Sep-30-2018**
" Very nice place well worth the money...." - Brad
Save $157 Photo of Family-Friendly Apartment Close to Siena
  • min $981/wk
  • max $1,565/wk
  • min $883/wk
  • max $1,409/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $157 when you book by Sep-30-2018**
" The time spent at Terra di Siena was wonderful and I would go back in a heartbeat...." - Vallerie
Save $1,563 Photo of Large Villa with Pool and Guest House in Chianti
  • min $9,012/wk
  • max $15,628/wk
  • min $8,111/wk
  • max $14,065/wk
  • Min Stay: 7 days
Sleeps 14 to 18 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,563 when you book by Sep-30-2018**
Save $124 Photo of House Rental in Tuscany, Siena
  • min $1,050/wk
  • max $1,239/wk
  • min $945/wk
  • max $1,115/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 bathrooms
  • Independent House
  • Maid Service
  • Air Conditioning
** Save up to $124 when you book by Sep-30-2018**
Save $291 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,689/wk
  • max $2,913/wk
  • min $1,520/wk
  • max $2,622/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 $291 when you book by Sep-30-2018**
" Amazing! We felt like we were part of a family on the property - Sandra, Nicolo, and all the staff were so friendly and helpful. The whole experience made us fee..." - Rayna
Save $257 Photo of Family-Friendly Farmhouse Close to Siena
  • min $1,275/wk
  • max $2,573/wk
  • min $1,148/wk
  • max $2,316/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $257 when you book by Sep-30-2018**
" The view of the hills, grape orchard, and olive trees...." - Ann
Save $956 Photo of Chianti Villa near a Charming Village
  • min $5,146/wk
  • max $9,557/wk
  • min $4,631/wk
  • max $8,601/wk
  • Min Stay: 3 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $956 when you book by Sep-30-2018**
" Everything was fine...." - William
 
Displaying 1 to 30 of 64 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..