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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 Aug-20-2022**
" 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 Aug-20-2022**
" Fantastic - Sandro and Nelson were excellent hosts...." - Peggy
Save $929 Photo of Stunning  Montepulciano  villa    close  to  city  center,  with  views,  pool,  within  walking  distance  to  restaurants,  wine-tasting  and  shops!
  • min $5,717/wk
  • max $9,287/wk
  • min $5,145/wk
  • max $8,358/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $929 when you book by Aug-20-2022**
" It was a dream vacation. It was one of the few times in my life that the reality exceeded my expectations. ..." - Marjorie
Save $560 Photo of Chianti Tuscany Villa Rental, Near Siena
  • min $3,600/wk
  • max $5,601/wk
  • min $3,240/wk
  • max $5,041/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 $560 when you book by Aug-20-2022**
" 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 $108 Photo of Apartment Farmhouse in Tuscany
  • min $925/wk
  • max $1,079/wk
  • min $833/wk
  • max $971/wk
  • Min Stay: 4 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $108 when you book by Aug-20-2022**
" 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
Save $1,278 Photo of Large Chianti Classico Villa with Swimming Pool and Spa near Siena
  • min $11,622/wk
  • max $12,784/wk
  • min $10,460/wk
  • max $11,506/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 10 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,278 when you book by Aug-20-2022**
" 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
Save $748 Photo of Farmhouse Rental in Chianti Area of Tuscany
  • min $3,441/wk
  • max $7,484/wk
  • min $3,097/wk
  • max $6,736/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 $748 when you book by Aug-20-2022**
" 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 $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 Aug-20-2022**
" 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 $1,009 Photo of Villa Rental in Tuscany, Montalcino
  • min $5,761/wk
  • max $10,092/wk
  • min $5,185/wk
  • max $9,083/wk
  • Min Stay: 7 days
Sleeps 11 to 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
** Save up to $1,009 when you book by Aug-20-2022**
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 Aug-20-2022**
" A wonderful experience at the villa...." - John
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 Aug-20-2022**
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 Aug-20-2022**
" It was fantastic. ..." - Jessica
Save $1,760 Photo of Villa Rental in Tuscany, Castelnuova Berardenga
  • min $11,220/wk
  • max $17,601/wk
  • min $10,098/wk
  • max $15,841/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
** Save up to $1,760 when you book by Aug-20-2022**
Save $3,198 Photo of Converted farmhouse and cottages with pool in the heart of Tuscany wine country.
  • min $25,288/wk
  • max $31,982/wk
  • min $22,759/wk
  • max $28,784/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
** Save up to $3,198 when you book by Aug-20-2022**
Save $1,437 Photo of Villa Rental in Tuscany, Monteroni D'Arbia
  • min $8,900/wk
  • max $14,374/wk
  • min $8,010/wk
  • max $12,937/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 7 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,437 when you book by Aug-20-2022**
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 Aug-20-2022**
" 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
Save $1,909 Photo of Large Chic Tuscany Villa with Private Guest House and Al Fresco Dining
  • min $12,163/wk
  • max $19,093/wk
  • min $10,947/wk
  • max $17,184/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,909 when you book by Aug-20-2022**
" Our 4 weeks at Villa Brunello were everything we could have dreamed and more! The PERFECT Tuscan experience in every way!..." - Matt
Save $130 Photo of House Rental in Tuscany, Siena
  • min $1,207/wk
  • max $1,295/wk
  • min $1,086/wk
  • max $1,166/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 bathrooms
  • Independent House
  • Maid Service
  • Air Conditioning
** Save up to $130 when you book by Aug-20-2022**
Save $1,555 Photo of Villa Rental in Tuscany, Lucignano d'Asso
  • min $13,653/wk
  • max $15,550/wk
  • min $12,288/wk
  • max $13,995/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,555 when you book by Aug-20-2022**
Save $287 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $1,324/wk
  • max $2,869/wk
  • min $1,192/wk
  • max $2,582/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 $287 when you book by Aug-20-2022**
" 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
Save $864 Photo of Villa Rental in Tuscany, Montalcino
  • min $7,390/wk
  • max $8,636/wk
  • min $6,651/wk
  • max $7,772/wk
  • Min Stay: 3 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $864 when you book by Aug-20-2022**
Save $3,150 Photo of Luxury Villa Rental Near Siena
  • min $28,004/wk
  • max $31,504/wk
  • min $25,204/wk
  • max $28,354/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 $3,150 when you book by Aug-20-2022**
" The villa was lovely...." - Phyllis
Save $219 Photo of Country Villa in heart of Chianti centrally located close to regions’ history, art, restaurants.
  • min $878/wk
  • max $2,193/wk
  • min $790/wk
  • max $1,974/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 $219 when you book by Aug-20-2022**
" When we arrived Maria had wine, fruit, bread, apricot jam (my favourite) and goodies for us (what a lovely touch)! A charcoal BBQ on the patio as you went into th..." - Judy
Save $412 Photo of House Rental in Tuscany, Buonconvento
  • min $1,925/wk
  • max $4,117/wk
  • min $1,733/wk
  • max $3,705/wk
  • Min Stay: 7 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $412 when you book by Aug-20-2022**
Save $616 Photo of Charming Villa with Pool in Tuscany
  • min $3,921/wk
  • max $6,161/wk
  • min $3,529/wk
  • max $5,545/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 $616 when you book by Aug-20-2022**
" Very Good. A little too far from grocery store and Florence...." - Mary
Save $448 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $2,064/wk
  • max $4,480/wk
  • min $1,858/wk
  • max $4,032/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 $448 when you book by Aug-20-2022**
" Very nice and restful. S..." - Olenka
Save $866 Photo of Farmhouse in the Chianti Region for Friends or a Large Family
  • min $4,324/wk
  • max $8,664/wk
  • min $3,892/wk
  • max $7,798/wk
  • Min Stay: 7 days
Sleeps 11 people
  • 1 single bedrooms
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $866 when you book by Aug-20-2022**
" Terrific! Everything worked, the villa was comfortable and very clean, and it was wonderful to be out in the countryside and simultaneously next to a substantiall..." - Alexander
Save $248 Photo of Farmhouse Rental in Tuscany, San Giovanni
  • min $1,167/wk
  • max $2,480/wk
  • min $1,050/wk
  • max $2,232/wk
  • Min Stay: 3 days
Sleeps 2 to 6 people
  • 1 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $248 when you book by Aug-20-2022**
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 Aug-20-2022**
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 Aug-20-2022**
 
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..