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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 Oct-31-2018**
" 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 Oct-31-2018**
" It was a wonderful stay. The scenery was stunning, and the owners were very thoughtful and accommodating. We loved all the space, which made it easy for our group ..." - Nicole
Save $1,232 Photo of Apartment Farmhouse in Tuscany
  • min $1,025/wk
  • max $1,295/wk
  • min $820/wk
  • max $1,036/wk
  • Min Stay: 4 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,232 when you book by Oct-31-2018**
" It was a very nice time. Claudia and Rudi were great and wonderful hosts. Pizza parties were really special times...." - Allen
Save $925 Photo of Farmhouse Rental in Tuscany, Montalcino
  • min $2,751/wk
  • max $4,623/wk
  • min $2,201/wk
  • max $3,699/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 $925 when you book by Oct-31-2018**
" Very cozy property, although a tiny kitchen for a property of that size...." - Anne
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 Oct-31-2018**
" 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 $748 Photo of Apartment in Siena Overlooking the Famous Piazza del Campo
  • min $2,296/wk
  • max $3,739/wk
  • min $1,837/wk
  • max $2,991/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
** Save up to $748 when you book by Oct-31-2018**
" Very good...." - Kenneth
Save $1,474 Photo of Farmhouse Rental in Chianti Area of Tuscany
  • min $3,205/wk
  • max $7,368/wk
  • min $2,564/wk
  • max $5,894/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 $1,474 when you book by Oct-31-2018**
" 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 $1,604 Photo of Tuscany Villa near Siena with Private Pool
  • min $2,055/wk
  • max $8,022/wk
  • min $1,644/wk
  • max $6,418/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 2 single bedrooms
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,604 when you book by Oct-31-2018**
" Very good. The property management had lots of cheeses, meats, bread and wine for us upon arrival. Both kitchens were well stocked with glassware, dishes, pots an..." - Johnnie Lynn
Save $4,021 Photo of Large Chic Tuscany Villa with Private Guest House and Al Fresco Dining
  • min $12,806/wk
  • max $20,103/wk
  • min $10,245/wk
  • max $16,082/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $4,021 when you book by Oct-31-2018**
" Our 4 weeks at Villa Brunello were everything we could have dreamed and more! The PERFECT Tuscan experience in every way!..." - Matt
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 Oct-31-2018**
" Very Good. A little too far from grocery store and Florence...." - Mary
Save $312 Photo of Charming Apartment on a Large Estate in Monticchiello
  • min $2,353/wk
  • max $3,117/wk
  • min $2,118/wk
  • max $2,805/wk
  • Min Stay: 5 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $312 when you book by Oct-31-2018**
" We had a fabulous time and would do it again in a heartbeat. ..." - Susan
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 Oct-31-2018**
" The villa was lovely...." - Phyllis
Save $1,078 Photo of Chianti Tuscany Villa Rental, Near Siena
  • min $3,505/wk
  • max $5,391/wk
  • min $2,804/wk
  • max $4,313/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 $1,078 when you book by Oct-31-2018**
" We had a wonderful time at the property..." - Leo
Save $657 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $1,511/wk
  • max $3,286/wk
  • min $1,209/wk
  • max $2,629/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $657 when you book by Oct-31-2018**
" 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
Save $893 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $2,058/wk
  • max $4,467/wk
  • min $1,646/wk
  • max $3,574/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 $893 when you book by Oct-31-2018**
" Very nice and restful. S..." - Olenka
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 Oct-31-2018**
" Our group of ten had a very enjoyable experience at the property...." - Marv
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 Oct-31-2018**
" The time spent at Terra di Siena was wonderful and I would go back in a heartbeat...." - Vallerie
Save $3,438 Photo of Large Villa with Pool and Guest House in Chianti
  • min $9,913/wk
  • max $17,191/wk
  • min $7,931/wk
  • max $13,753/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 $3,438 when you book by Oct-31-2018**
Save $6,035 Photo of Historic Tuscan Villa with Cottage with Private Pool and Tennis Court
  • min $20,193/wk
  • max $30,173/wk
  • min $16,154/wk
  • max $24,138/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 $6,035 when you book by Oct-31-2018**
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 Oct-31-2018**
Save $2,909 Photo of Villa in Southern Tuscany with Privacy and Views
  • min $9,240/wk
  • max $14,543/wk
  • min $7,392/wk
  • max $11,634/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 $2,909 when you book by Oct-31-2018**
" Very good...." - Bill
Save $445 Photo of Charming Tuscany Apartment Walking Distance to town
  • min $1,780/wk
  • max $2,224/wk
  • min $1,424/wk
  • max $1,779/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
  • Air Conditioning
** Save up to $445 when you book by Oct-31-2018**
" Excellent overall experience. Property managers are the owners and are very nice and hospitable. ..." - Ralph
Save $794 Photo of Farmhouse in Southern Tuscany with Pool
  • min $2,151/wk
  • max $3,970/wk
  • min $1,720/wk
  • max $3,176/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 $794 when you book by Oct-31-2018**
" The view was great. ..." - Charlotte
Save $534 Photo of Charming Tuscany Apartment Walking Distance to town
  • min $2,076/wk
  • max $2,669/wk
  • min $1,661/wk
  • max $2,135/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 $534 when you book by Oct-31-2018**
" 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 $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
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $202 when you book by Oct-31-2018**
" Nice small property with charming hosts in a pretty area...." - Sara
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 Oct-31-2018**
" Excellent. In this unit were my wife's mom and our 11 year old twins. They spent more time in the facility while we went out sightseeing more. They loved the a..." - Curtis
Save $300 Photo of Charming Tuscany Apartment Walking Distance to town
  • min $2,157/wk
  • max $3,002/wk
  • min $1,941/wk
  • max $2,702/wk
  • Min Stay: 3 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
  • Air Conditioning
** Save up to $300 when you book by Oct-31-2018**
" We had a very relaxing and enjoyable time at Casa dei Venti - La Tempesta. Our host, Filippo, was very kind and generous and helped us with several outings in the ..." - Jim
Save $1,488 Photo of Villa Rental in Tuscany, Montalcino
  • min $6,360/wk
  • max $7,438/wk
  • min $5,088/wk
  • max $5,951/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 $1,488 when you book by Oct-31-2018**
Save $589 Photo of Tuscany Villa with Private Pool
  • min $3,199/wk
  • max $5,887/wk
  • min $2,879/wk
  • max $5,298/wk
  • Min Stay: 7 days
Sleeps 16 to 17 people
  • 8 double bedrooms
  • 7 bathrooms
  • Independent House
  • Washing Machine
  • Maid Service
** Save up to $589 when you book by Oct-31-2018**
" We had a great experience. The owner, Antonella, was exceptionally helpful in so many ways. The property is lovely, and a great deal of thought has been given to..." - Felice
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 Oct-31-2018**
" 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
 
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..