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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 83 villas
Save $1,068 Photo of Cozy Tuscan Villa near Montepulciano
  • min $5,881/wk
  • max $10,677/wk
  • min $5,293/wk
  • max $9,609/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 $1,068 when you book by Dec-10-2022**
" This was our second visit to this beautiful property. This time we stayed 2 weeks. The villa is beautiful and our family of twelve would definitely stay there ga..." - Stephen
Save $990 Photo of Villa on Large Estate Near San Gimignano
  • min $5,625/wk
  • max $9,900/wk
  • min $5,063/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 Dec-10-2022**
" Fantastic - Sandro and Nelson were excellent hosts...." - Peggy
Save $262 Photo of Apartment in Siena Overlooking the Famous Piazza del Campo
  • $2,615/wk
  • $2,354/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
** Save up to $262 when you book by Dec-10-2022**
" We loved this apt. It is located in the heart of Siena right on Il Campo, the main square and one of the great public spaces of any city in the world. The apt is v..." - Gregory
Save $3,632 Photo of Large Estate with Historic Villa and Two Farmhouses for a Large Group
  • $36,322/wk
  • $32,690/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 Dec-10-2022**
" The historical impact of the villa made it magical. ..." - Mike
Save $3,501 Photo of Estate Rental in Tuscany, Gaiole in Chianti (Chianti Area)
  • min $21,528/wk
  • max $35,005/wk
  • min $19,375/wk
  • max $31,505/wk
  • Min Stay: 7 days
Sleeps 28 people
  • 14 double bedrooms
  • 10 bathrooms
  • Independent House
  • Swimming Pool
** Save up to $3,501 when you book by Dec-10-2022**
Save $1,009 Photo of Beautiful Farmhouse in the Chianti Near Town
  • min $5,775/wk
  • max $10,092/wk
  • min $5,198/wk
  • max $9,083/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 $1,009 when you book by Dec-10-2022**
" The property itself was very pretty with amazing views. It was centrally located and fairly easy to access. ..." - Jacqueline
Save $245 Photo of Tuscany Villa Rental
  • min $1,559/wk
  • max $2,449/wk
  • min $1,403/wk
  • max $2,204/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $245 when you book by Dec-10-2022**
" 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
  • Enquire for Rates
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" It was an awesome experience. This property has it all. A couple of nights they provide a restaurant dining experience with great ambience. The owners are gracious..." - Charles
Save $2,053 Photo of Villa Rental in Tuscany, Buonconvento
  • min $14,374/wk
  • max $20,526/wk
  • min $12,937/wk
  • max $18,473/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $2,053 when you book by Dec-10-2022**
Save $1,165 Photo of Tuscan farmhouse with pool a rural retreat in the Crete Senesi near Siena
  • min $6,230/wk
  • max $11,648/wk
  • min $5,607/wk
  • max $10,483/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,165 when you book by Dec-10-2022**
Save $1,008 Photo of Villa Rental in Tuscany, Monticchiello
  • min $4,061/wk
  • max $10,082/wk
  • min $3,655/wk
  • max $9,074/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,008 when you book by Dec-10-2022**
  • Enquire for Rates
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
  • Enquire for Rates
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
  • Enquire for Rates
Sleeps 8 people
  • 4 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
  • Enquire for Rates
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" 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
Save $123 Photo of Vacation Rental Agritourism in Tuscany
  • $1,233/wk
  • $1,110/wk
  • Min Stay: 4 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $123 when you book by Dec-10-2022**
" Our stay greatly facilitated the overall enjoyment of our experience in Tuscany. It is centrally located, and provided easy access to all of the places we wanted ..." - William
Save $1,010 Photo of Large Farmhouse on a Wine Estate near Siena Fit for Families
  • min $5,758/wk
  • max $10,098/wk
  • min $5,182/wk
  • max $9,088/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,010 when you book by Dec-10-2022**
" A wonderful experience at the villa...." - John
  • Enquire for Rates
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" We loved the location the restored mill was beautiful, the home decor (mostly antiques were interesting), the internet was highly variable and could have lived for..." - Thomas
Save $572 Photo of Stunning  Montepulciano  villa    close  to  city  center,  with  views,  pool,  within  walking  distance  to  restaurants,  wine-tasting  and  shops!
  • $5,717/wk
  • $5,145/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $572 when you book by Dec-10-2022**
" It was a dream vacation. It was one of the few times in my life that the reality exceeded my expectations. ..." - Marjorie
  • Enquire for Rates
Sleeps 25 people
  • 3 single bedrooms
  • 11 double bedrooms
  • 14 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" The villa was lovely...." - Phyllis
Save $1,295 Photo of Large Villa with Pool and Guest House in Chianti
  • min $9,415/wk
  • max $12,950/wk
  • min $8,474/wk
  • max $11,655/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 $1,295 when you book by Dec-10-2022**
Save $1,260 Photo of Beautiful Chianti Villa with Guest Cottage and Private Infinity Pool
  • min $11,342/wk
  • max $12,602/wk
  • min $10,208/wk
  • max $11,342/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,260 when you book by Dec-10-2022**
" It was fantastic. ..." - Jessica
  • Enquire for Rates
Sleeps 18 people
  • 9 double bedrooms
  • 10 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" The property is beautiful. It seems to have been a hotel at some point so each room has a well appointed bathroom. The kitchen is a commercial kitchen which is v..." - Julia
  • $925/wk
  • $833/wk
  • Min Stay: 4 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $93 when you book by Dec-10-2022**
" it exceeded our expectation. Claudia and Rudy were the perfect host, made use feel like family right from the start. invited us to partake in making and cooking re..." - Katheryn
  • Enquire for Rates
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
" We had a wonderful time at Rosalia and in Lilliano. The house was huge and had everything we needed, including a high chair and washing machine, extra blankets. ..." - Holly
Save $474 Photo of Farmhouse Rental in Chianti Area of Tuscany
  • min $3,441/wk
  • max $4,744/wk
  • min $3,097/wk
  • max $4,270/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 $474 when you book by Dec-10-2022**
" 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 $2,380 Photo of Villa Rental in Tuscany, Casole d'Elsa
  • min $12,613/wk
  • max $23,800/wk
  • min $11,352/wk
  • max $21,420/wk
  • Min Stay: 4 days
Sleeps 30 people
  • 8 single bedrooms
  • 11 double bedrooms
  • 16 bathrooms
  • Independent House
  • Swimming Pool
** Save up to $2,380 when you book by Dec-10-2022**
Save $1,298 Photo of Villa Rental in Tuscany, Montalcino
  • min $6,844/wk
  • max $12,980/wk
  • min $6,160/wk
  • max $11,682/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Swimming Pool
  • Air Conditioning
** Save up to $1,298 when you book by Dec-10-2022**
Save $1,520 Photo of Villa Rental in Tuscany, San Casciano dei Bagni
  • min $14,000/wk
  • max $15,197/wk
  • min $12,600/wk
  • max $13,677/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $1,520 when you book by Dec-10-2022**
Save $1,654 Photo of Villa Rental in Tuscany, Radicofani
  • $16,538/wk
  • $14,884/wk
  • Min Stay: 7 days
Sleeps 17 people
  • 1 single bedrooms
  • 8 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,654 when you book by Dec-10-2022**
 
Displaying 1 to 30 of 83 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..