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Italy Accommodations Chianti Tuscany Villa Rentals

Nestled amidst the hills and valleys of the Sienese Chianti-a territory dominated by medieval hill towns---Siena offers a wonderfully preserved example of the Tuscan Middle Ages. The city is home to many Gothic palaces, churches, and museums filled with Gothic art.   Continue >

Displaying 1 to 30 of 88 villas
Save $1,008 Photo of Cozy Tuscan Villa near Montepulciano
  • min $5,461/wk
  • max $10,082/wk
  • min $4,915/wk
  • max $9,074/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,008 when you book by Jan-31-2021**
" There were 13 of us, 8 adults and 5 children ages 6 to 10. All had a great time and there was plenty of room for all. The adults particularly enjoyed sitting on th..." - Michael
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 Jan-31-2021**
" When we arrived Maria had wine, fruit, bread, apricot jam (my favourite) and goodies for us (what a lovely touch)! A charcoal BBQ on the patio as you went into th..." - Judy
Save $713 Photo of Farmhouse Rental in Chianti Area of Tuscany
  • min $3,277/wk
  • max $7,127/wk
  • min $2,949/wk
  • max $6,414/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 $713 when you book by Jan-31-2021**
" We were three couples staying at Villa Adelina, and all of us loved our stay. The villa was clean, a bit rustic but very comfortable for our home away from home f..." - Janet
Save $296 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $2,157/wk
  • max $2,955/wk
  • min $1,941/wk
  • max $2,660/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $296 when you book by Jan-31-2021**
" It's an amazing property. We had space galore and help when we needed it. The location is very central in Tuscany, so it makes a great home base for daily excu..." - Steven
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 Jan-31-2021**
" Great experience in a spectacular villa...." - Viviane
Save $532 Photo of Chianti Tuscany Villa Rental, Near Siena
  • min $3,221/wk
  • max $5,321/wk
  • min $2,899/wk
  • max $4,789/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 $532 when you book by Jan-31-2021**
" Absolutely excellent. ..." - Kerby
Save $237 Photo of Farmhouse Rental in Tuscany, San Giovanni
  • min $1,118/wk
  • max $2,372/wk
  • min $1,006/wk
  • max $2,135/wk
  • Min Stay: 7 days
Sleeps 2 to 6 people
  • 1 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $237 when you book by Jan-31-2021**
Save $896 Photo of Stunning  Montepulciano  villa    close  to  city  center,  with  views,  pool,  within  walking  distance  to  restaurants,  wine-tasting  and  shops!
  • min $5,515/wk
  • max $8,959/wk
  • min $4,964/wk
  • max $8,063/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $896 when you book by Jan-31-2021**
" We loved this experience! We were there for 2 weeks in August and had different groups of people coming to stay with us. The property is part of a working farm (..." - Marty
Save $2,450 Photo of Luxury Villa Rental Near Siena
  • min $21,703/wk
  • max $24,503/wk
  • min $19,533/wk
  • max $22,053/wk
  • Min Stay: 7 days
Sleeps 25 people
  • 3 single bedrooms
  • 11 double bedrooms
  • 14 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $2,450 when you book by Jan-31-2021**
" The villa was lovely...." - Phyllis
Save $124 Photo of House Rental in Tuscany, Siena
  • min $1,155/wk
  • max $1,239/wk
  • min $1,040/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 Jan-31-2021**
Save $990 Photo of Villa on Large Estate Near San Gimignano
  • min $5,300/wk
  • max $9,900/wk
  • min $4,770/wk
  • max $8,910/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $990 when you book by Jan-31-2021**
" Villa Dora exceeded our expectations in every way! We were a family of 6 adults and every one of us fell in love with the villa!..." - Lynn
Save $340 Photo of Apartment in Siena Overlooking the Famous Piazza del Campo
  • min $2,615/wk
  • max $3,399/wk
  • min $2,354/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 Jan-31-2021**
" Very good...." - Kenneth
Save $734 Photo of Villa Rental in Tuscany, Montalcino
  • min $6,674/wk
  • max $7,341/wk
  • min $6,007/wk
  • max $6,607/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $734 when you book by Jan-31-2021**
Save $1,582 Photo of Villa Rental in Tuscany, Castelnuova Berardenga
  • min $11,599/wk
  • max $15,820/wk
  • min $10,439/wk
  • max $14,238/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
** Save up to $1,582 when you book by Jan-31-2021**
Save $931 Photo of Rustic Countryside Villa with Pool near San Casciano dei Bagni
  • min $5,881/wk
  • max $9,312/wk
  • min $5,293/wk
  • max $8,381/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $931 when you book by Jan-31-2021**
" Wonderful - We stayed at Villa Orcia with 10 adults and there was plenty of room for everyone. Patrizia is extremely helpful...." - Renee
Save $490 Photo of Farmhouse in Southern Tuscany with Pool
  • min $2,801/wk
  • max $4,901/wk
  • min $2,521/wk
  • max $4,411/wk
  • Min Stay: 7 days
Sleeps 8 to 9 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $490 when you book by Jan-31-2021**
" The view was great. ..." - Charlotte
Save $1,633 Photo of Large Villa with Pool and Guest House in Chianti
  • min $9,415/wk
  • max $16,328/wk
  • min $8,474/wk
  • max $14,695/wk
  • Min Stay: 7 days
Sleeps 14 to 16 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,633 when you book by Jan-31-2021**
Save $401 Photo of House Rental in Tuscany, Buonconvento
  • min $1,881/wk
  • max $4,013/wk
  • min $1,693/wk
  • max $3,612/wk
  • Min Stay: 7 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $401 when you book by Jan-31-2021**
Save $1,765 Photo of Villa Rental in Tuscany, Buonconvento
  • min $10,086/wk
  • max $17,651/wk
  • min $9,077/wk
  • max $15,886/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,765 when you book by Jan-31-2021**
Save $581 Photo of Charming Villa with Pool in Tuscany
  • min $3,676/wk
  • max $5,811/wk
  • min $3,308/wk
  • max $5,230/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 $581 when you book by Jan-31-2021**
" Very Good. A little too far from grocery store and Florence...." - Mary
Save $404 Photo of Farmhouse Rental in Tuscany, Montalcino
  • min $2,399/wk
  • max $4,039/wk
  • min $2,159/wk
  • max $3,635/wk
  • Min Stay: 7 days
Sleeps 7 people
  • 1 single bedrooms
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $404 when you book by Jan-31-2021**
" Very cozy property, although a tiny kitchen for a property of that size...." - Anne
Save $324 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $2,353/wk
  • max $3,235/wk
  • min $2,118/wk
  • max $2,912/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $324 when you book by Jan-31-2021**
" Except for a cooking class at the estate, we spent our time traveling to Siena, Florence, Cinque Terre, and the Chianti region during our 5 night stay. I'd ra..." - Bob
Save $273 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $1,261/wk
  • max $2,734/wk
  • min $1,135/wk
  • max $2,461/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 $273 when you book by Jan-31-2021**
" 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 $427 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $1,966/wk
  • max $4,267/wk
  • min $1,769/wk
  • max $3,840/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 $427 when you book by Jan-31-2021**
" Very nice and restful. S..." - Olenka
Save $1,151 Photo of Tuscan farmhouse with pool a rural retreat in the Crete Senesi near Siena
  • min $5,228/wk
  • max $11,506/wk
  • min $4,705/wk
  • max $10,355/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,151 when you book by Jan-31-2021**
Save $3,632 Photo of Large Estate with Historic Villa and Two Farmhouses for a Large Group
  • min $36,322/wk
  • max $36,323/wk
  • min $32,690/wk
  • max $32,691/wk
  • Min Stay: 3 days
Sleeps 38 people
  • 19 double bedrooms
  • 15 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $3,632 when you book by Jan-31-2021**
" The historical impact of the villa made it magical. ..." - Mike
Save $1,405 Photo of Villa Rental in Tuscany, Lucignano d'Asso
  • min $12,433/wk
  • max $14,053/wk
  • min $11,190/wk
  • max $12,648/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,405 when you book by Jan-31-2021**
Save $314 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $1,443/wk
  • max $3,137/wk
  • min $1,299/wk
  • max $2,823/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $314 when you book by Jan-31-2021**
" 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
Save $210 Photo of Tuscany Villa Rental
  • min $1,470/wk
  • max $2,100/wk
  • min $1,323/wk
  • max $1,890/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $210 when you book by Jan-31-2021**
" Enjoyed location due to plenty of hiking opportunities with our dog. The property is fine for two people or perhaps a small family. Wouldn't recommend it for t..." - Peter
Save $809 Photo of Farmhouse Rental in Tuscany, Gaiole in Chianti (Chianti Area)
  • min $7,088/wk
  • max $8,089/wk
  • min $6,379/wk
  • max $7,280/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $809 when you book by Jan-31-2021**
" 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
 
Displaying 1 to 30 of 88 villas

Dating back to 1310, the Palio delle Contrade is an annual bareback horse race in which 10 of the city's 17 contrade (neighborhoods) compete. The culminating event of Italy's most spectacular festival, the biggest race is held on August 16; a smaller race is held on July 2nd. In the environs of Radda in Chianti, wine estates such as Castello di Volpaia and Badia a Coltibuono are satisfying side trips for wine and olive oil lovers. Heading northwest of Siena towards San Gimignano, Monteriggioni, one of Italy's most perfectly preserved fortified villages, dominates the vista..