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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 106 villas
Save $924 Photo of Cozy Tuscan Villa near Montepulciano
  • min $4,761/wk
  • max $9,242/wk
  • min $4,285/wk
  • max $8,318/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 $924 when you book by Dec-20-2018**
" Fantastic experience with a beautiful area and facility...." - Kennth
Save $930 Photo of Villa on Large Estate Near San Gimignano
  • min $4,500/wk
  • max $9,300/wk
  • min $4,050/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 Dec-20-2018**
" Wonderful stay at the property. ..." - Robin
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 Dec-20-2018**
" Very good. The property was well located. ..." - Rick
Save $578 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 $578 when you book by Dec-20-2018**
" Beautiful property. We enjoyed being on such a lovely property. The apartment was quite comfortable, nothing fancy...." - Kaireen
Save $340 Photo of Apartment in Siena Overlooking the Famous Piazza del Campo
  • min $2,416/wk
  • max $3,399/wk
  • min $2,174/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 Dec-20-2018**
" Very good...." - Kenneth
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 Dec-20-2018**
" The villa is perched on a hillside with wonderful views and that set the stage for my wife's wish to have friends and family enjoy the Tuscan countryside with ..." - Chris
Save $1,828 Photo of Large Chic Tuscany Villa with Private Guest House and Al Fresco Dining
  • min $11,642/wk
  • max $18,275/wk
  • min $10,478/wk
  • max $16,448/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,828 when you book by Dec-20-2018**
" Our 4 weeks at Villa Brunello were everything we could have dreamed and more! The PERFECT Tuscan experience in every way!..." - Matt
  • $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 Dec-20-2018**
" The location was perfect, both in relation to the town, and to the parking...." - Christine
Save $1,372 Photo of Rustic Countryside Villa with Pool near San Casciano dei Bagni
  • min $6,861/wk
  • max $13,722/wk
  • min $6,175/wk
  • max $12,350/wk
  • Min Stay: 3 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,372 when you book by Dec-20-2018**
" Wonderful - We stayed at Villa Orcia with 10 adults and there was plenty of room for everyone. Patrizia is extremely helpful...." - Renee
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 16 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,563 when you book by Dec-20-2018**
Save $420 Photo of Farmhouse Rental in Tuscany, Montalcino
  • min $2,501/wk
  • max $4,203/wk
  • min $2,251/wk
  • max $3,783/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 $420 when you book by Dec-20-2018**
" Very cozy property, although a tiny kitchen for a property of that size...." - Anne
Save $1,050 Photo of Villa in Southern Tuscany with Privacy and Views
  • min $8,400/wk
  • max $10,500/wk
  • min $7,560/wk
  • max $9,450/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 $1,050 when you book by Dec-20-2018**
" Very good...." - Bill
  • $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 Dec-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 $202 Photo of Charming Tuscany Apartment Walking Distance to town
  • min $1,618/wk
  • max $2,022/wk
  • min $1,456/wk
  • max $1,820/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
  • Air Conditioning
** Save up to $202 when you book by Dec-20-2018**
" Excellent overall experience. Property managers are the owners and are very nice and hospitable. ..." - Ralph
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 Dec-20-2018**
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 Dec-20-2018**
" This property is well situated and is quite comfortable for 2 couples...." - Sonia
Save $2,743 Photo of Historic Tuscan Villa with Cottage with Private Pool and Tennis Court
  • min $18,357/wk
  • max $27,430/wk
  • min $16,521/wk
  • max $24,687/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $2,743 when you book by Dec-20-2018**
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 Dec-20-2018**
Save $1,330 Photo of Spacious and Beautiful Tuscany Villa Near Montalcino
  • min $8,074/wk
  • max $13,300/wk
  • min $7,267/wk
  • max $11,970/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,330 when you book by Dec-20-2018**
" Relaxing We loved it. The stunning views really made us know we were in Tuscany...probably the most beautiful part of Tuscany. Although narrow winding dirt roads ..." - Val
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 Dec-20-2018**
" Great. Claudia and Rudi terrific ..." - Frank
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 Dec-20-2018**
Save $967 Photo of Beautiful Farmhouse in the Chianti Near Town
  • min $5,528/wk
  • max $9,665/wk
  • min $4,975/wk
  • max $8,699/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 $967 when you book by Dec-20-2018**
" We had a wonderful, peaceful time...." - Davis
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 Dec-20-2018**
" Wonderful...." - Fred
Save $2,240 Photo of Luxury Villa Rental Near Siena
  • min $19,603/wk
  • max $22,403/wk
  • min $17,643/wk
  • max $20,163/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 $2,240 when you book by Dec-20-2018**
" The villa was lovely...." - Phyllis
Save $243 Photo of Charming Tuscany Apartment Walking Distance to town
  • min $1,887/wk
  • max $2,426/wk
  • min $1,698/wk
  • max $2,183/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $243 when you book by Dec-20-2018**
" We had a grand time. The staff were kind and exceedingly helpful. The town was a bit quiet, but we were close to some beautiful towns. ..." - Jamie
Save $485 Photo of Villa Rental in Tuscany, Castlenuovo dell'Abate
  • min $4,667/wk
  • max $4,853/wk
  • min $4,200/wk
  • max $4,368/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $485 when you book by Dec-20-2018**
Save $147 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $976/wk
  • max $1,472/wk
  • min $878/wk
  • max $1,325/wk
  • Min Stay: 5 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $147 when you book by Dec-20-2018**
" It was amazing. Everything was very well done...." - Simin
Save $150 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,000/wk
  • max $1,504/wk
  • min $900/wk
  • max $1,354/wk
  • Min Stay: 5 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $150 when you book by Dec-20-2018**
" Overall, the experience was positive. The apartment and grounds were spotless, exactly the way I like my home in the U.S. The family is very nice, attentive and he..." - Michelle
Save $200 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,248/wk
  • max $2,001/wk
  • min $1,123/wk
  • max $1,801/wk
  • Min Stay: 5 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $200 when you book by Dec-20-2018**
" Wonderful!..." - Peter
Save $812 Photo of Farmhouse on Historic Estate in the Chianti
  • min $4,464/wk
  • max $8,123/wk
  • min $4,018/wk
  • max $7,311/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 $812 when you book by Dec-20-2018**
" Our group of ten had a very enjoyable experience at the property...." - Marv
 
Displaying 1 to 30 of 106 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. If you are looking for a villa or rental apartment for your romantic honeymoon, or a house with swimming pool for your family vacation, view our Siena Rental Accommodations..