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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 101 villas
  • min $4,500/wk
  • max $9,300/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 $4,761/wk
  • max $9,242/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 $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 $2,353/wk
  • max $3,117/wk
  • Min Stay: 5 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" We had a fabulous time and would do it again in a heartbeat. ..." - Susan
  • min $1,245/wk
  • max $2,307/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" 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
  • min $2,087/wk
  • max $2,416/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
" Very good...." - Kenneth
  • min $5,951/wk
  • max $7,186/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" We had a wonderful experience at this property. It was a perfect location close to Siena. ..." - Pennie
  • min $4,464/wk
  • max $8,123/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Our group of ten had a very enjoyable experience at the property...." - Marv
  • min $5,822/wk
  • max $7,822/wk
  • Min Stay: 5 days
Sleeps 14 people
  • 7 double bedrooms
  • 5 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
  • min $8,629/wk
  • max $10,935/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" 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
  • 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 $1,868/wk
  • max $7,293/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
" 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
  • min $8,544/wk
  • max $12,538/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 7 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • 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
  • 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
" Our 4 weeks at Villa Brunello were everything we could have dreamed and more! The PERFECT Tuscan experience in every way!..." - Matt
  • min $6,550/wk
  • max $10,905/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
  • Air Conditioning
  • 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 $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
" Absolutely wonderful. Experience enhanced by the warm hospitality of Claudia and Rudy - we left feeling like family friends not hospitality guests...." - Kay
  • 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 $19,603/wk
  • max $22,403/wk
  • Min Stay: 7 days
Sleeps 25 people
  • 3 single bedrooms
  • 11 double bedrooms
  • 14 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" The villa was lovely...." - Phyllis
  • min $961/wk
  • max $1,230/wk
  • Min Stay: 4 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Beautiful stay...." - Joan
  • $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 $14,553/wk
  • max $18,333/wk
  • Min Stay: 7 days
Sleeps 11 to 13 people
  • 1 single bedrooms
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
  • min $2,914/wk
  • max $6,698/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" 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 $961/wk
  • max $1,230/wk
  • Min Stay: 4 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" This was my second visit in five months! I love it!..." - Barbara
  • 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 $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 $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 $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 $8,111/wk
  • max $9,245/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
 
Displaying 1 to 30 of 101 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..