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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 >

Showing 1 to 30 of 97 properties
  • min $1,200/wk
  • max $8,100/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" The caretaker was fantastic upon our arrival! He provided an excellent tour and answered all of our questions. The villa exceeded my expectations and I have alre..." - Brandi
  • min $4,481/wk
  • max $9,032/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" This was an excellent choice. The villa itself was beautiful both inside and out. We were four couples with diverse interests and this was a great starting point e..." - Robert
  • min $8,074/wk
  • max $13,300/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" 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
  • min $12,328/wk
  • max $19,966/wk
  • Min Stay: 7 days
Sleeps 10 to 12 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" Great place...." - Kathy
  • min $1,762/wk
  • max $2,521/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" It was everything I had hoped for. We enjoyed the other guests and our privacy on the spacious grounds...." - Robert
  • min $932/wk
  • max $1,177/wk
  • Min Stay: 4 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Fantastic!!! This was our 4th time to return! Loved it and love Claudia, Rudi and Simone!..." - Dana
  • min $9,522/wk
  • max $12,602/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" Good...." - Jim
  • min $1,520/wk
  • max $1,814/wk
  • Min Stay: 4 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Wonderful...awesome!! It was so peaceful and relaxing, just what we needed! The hosts were very welcoming, friendly and helpful they gave us additional information..." - Anita
  • min $840/wk
  • max $1,881/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
  • min $3,186/wk
  • max $4,901/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" We had a wonderful time at the property..." - Leo
  • min $2,941/wk
  • max $5,321/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" There were three couples/friends sharing the villa. The three bedrooms downstairs were quite nice and all had their space. The owner was lovely. Accommodations for..." - Lee
  • min $2,280/wk
  • max $4,100/wk
  • Min Stay: 7 days
Sleeps 7 people
  • 1 single bedrooms
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" A beautiful place, close to town. Very pleasant gardens...." - Cherise
Save $1,179 Photo of Farmhouse Rental in Chianti Area of Tuscany
  • min $2,914/wk
  • max $6,698/wk
  • min $2,352/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,179 when you book by Nov-30-2017**
" Casa Luciana was perfect for the four couple who stayed there. It was a gorgeous place and actually had 6 bedrooms and 7 bathrooms. Loved it!! ..." - Nancy
  • min $2,039/wk
  • max $2,823/wk
  • Min Stay: 3 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
  • Air Conditioning
" We had an fantastic stay at Casa de Venti - La Tempesta. The facilities were excellent and the owners of the property were exceptionally kind and generous with the..." - Sally
  • min $1,335/wk
  • max $2,987/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
" We had a wonderful time. Yolanda is a sweetheart. Very accommodating and whatever issues we had, she handled them immediately and in a courteous manner. She ma..." - Jan
Save $1,179 Photo of Farmhouse Rental in Chianti Area of Tuscany
  • min $2,914/wk
  • max $6,698/wk
  • min $2,752/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 $1,179 when you book by Nov-30-2017**
" This was our second time at the property...." - Michael
  • min $2,087/wk
  • max $2,416/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
" Very good...." - Kenneth
  • min $3,641/wk
  • max $5,601/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Our group of six people - three couples - were delighted with the experience of sharing this beautiful villa for a week. ..." - Joan
  • min $7,616/wk
  • max $11,375/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $1,871/wk
  • max $4,061/wk
  • Min Stay: 7 days
Sleeps 9 people
  • 1 single bedrooms
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
" Extremely relaxing and enjoyable stay...." - Everett
  • min $3,500/wk
  • max $7,000/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" It was everything we hoped for and more. Everything was top notch, from the location to the amenities. Since we rented both apartments, it was very private...." - Norma
  • min $11,611/wk
  • max $12,850/wk
  • Min Stay: 3 days
Sleeps 18 people
  • 9 double bedrooms
  • 10 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
  • min $3,890/wk
  • max $6,125/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
  • min $2,352/wk
  • max $3,528/wk
  • Min Stay: 3 days
Sleeps 5 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Washing Machine
  • Maid Service
  • Air Conditioning
  • $7,980/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
" It was very pleasant. Getting there late at night and having a bottle of wine and homemade lasagna, olive oil and bread, was a very welcomed surprise...." - Janice
  • min $5,334/wk
  • max $9,665/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" 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
  • min $1,300/wk
  • max $1,950/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Owners were great. Nice people. Very informative. Property was very nice in good locations to go leave from for day trips...." - William
  • min $3,360/wk
  • max $4,667/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
" My visit to Italy was spectacular in part due to Villa Seggiano. The location and view were beautiful and the villa impeccably decorated. We had everything we ne..." - Susan
  • min $11,642/wk
  • max $18,275/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" All of us are seasoned travelers, some having traveled to Europe over 25 times. We agree that this was as close to perfect as any accommodation any of us have ever..." - Robert
  • min $5,881/wk
  • max $12,000/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
 
Showing 1 to 30 of 97 properties

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..