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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 99 villas
Save $1,925 Photo of Cozy Tuscan Villa near Montepulciano
  • min $5,041/wk
  • max $9,242/wk
  • min $4,537/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 $1,925 when you book by Sep-20-2019**
" Awesome ..." - Trent
Save $930 Photo of Villa on Large Estate Near San Gimignano
  • min $5,300/wk
  • max $9,300/wk
  • min $4,770/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 Sep-20-2019**
" Villa Dora is an extraordinary villa. Our experience was fantastic in every way...." - Rick
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 Sep-20-2019**
" The property was absolutely beautiful! Maria, the property manager, was wonderful and very accomodating. When we arrived, Maria had a vast arrangement of fruit and..." - Connie
Save $118 Photo of Apartment Farmhouse in Tuscany
  • min $932/wk
  • max $1,177/wk
  • min $839/wk
  • max $1,059/wk
  • Min Stay: 4 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $118 when you book by Sep-20-2019**
" Beautiful property. We enjoyed being on such a lovely property. The apartment was quite comfortable, nothing fancy...." - Kaireen
Save $1,389 Photo of Spacious and Beautiful Tuscany Villa Near Montalcino
  • min $8,432/wk
  • max $13,889/wk
  • min $7,589/wk
  • max $12,500/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,389 when you book by Sep-20-2019**
" 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
Save $252 Photo of Restored Farmhouse Surrounded by Vineyards and Olive Groves, Centrally Located in Tuscany
  • min $1,762/wk
  • max $2,521/wk
  • min $1,586/wk
  • max $2,269/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $252 when you book by Sep-20-2019**
" Great. Claudia and Rudi terrific ..." - Frank
Save $420 Photo of Farmhouse Rental in Tuscany, Montalcino
  • min $2,399/wk
  • max $4,203/wk
  • min $2,159/wk
  • max $3,783/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 $420 when you book by Sep-20-2019**
" Very cozy property, although a tiny kitchen for a property of that size...." - Anne
Save $1,294 Photo of Rustic Countryside Villa with Pool near San Casciano dei Bagni
  • min $6,077/wk
  • max $12,938/wk
  • min $5,469/wk
  • max $11,644/wk
  • Min Stay: 3 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,294 when you book by Sep-20-2019**
" Wonderful - We stayed at Villa Orcia with 10 adults and there was plenty of room for everyone. Patrizia is extremely helpful...." - Renee
Save $1,909 Photo of Large Chic Tuscany Villa with Private Guest House and Al Fresco Dining
  • min $12,157/wk
  • max $19,094/wk
  • min $10,941/wk
  • max $17,185/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 Sep-20-2019**
" Our 4 weeks at Villa Brunello were everything we could have dreamed and more! The PERFECT Tuscan experience in every way!..." - Matt
Save $340 Photo of Apartment in Siena Overlooking the Famous Piazza del Campo
  • min $2,615/wk
  • max $3,399/wk
  • min $2,354/wk
  • max $3,059/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
** Save up to $340 when you book by Sep-20-2019**
" Very good...." - Kenneth
Save $713 Photo of Farmhouse Rental in Chianti Area of Tuscany
  • min $3,277/wk
  • max $7,127/wk
  • min $2,949/wk
  • max $6,414/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 $713 when you book by Sep-20-2019**
" The villa is perched on a hillside with wonderful views and that set the stage for my wife's wish to have friends and family enjoy the Tuscan countryside with ..." - Chris
Save $518 Photo of Chianti Tuscany Villa Rental, Near Siena
  • min $2,451/wk
  • max $5,181/wk
  • min $2,206/wk
  • max $4,663/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 $518 when you book by Sep-20-2019**
" Absolutely excellent. ..." - Kerby
Save $902 Photo of Tuscan Farmhouse with Private Pool and Beautiful Views
  • min $5,880/wk
  • max $9,016/wk
  • min $5,292/wk
  • max $8,114/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $902 when you book by Sep-20-2019**
Save $896 Photo of Stunning  Montepulciano  villa    close  to  city  center,  with  views,  pool,  within  walking  distance  to  restaurants,  wine-tasting  and  shops!
  • min $5,515/wk
  • max $8,959/wk
  • min $4,964/wk
  • max $8,063/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $896 when you book by Sep-20-2019**
Save $210 Photo of Tuscany Villa Rental
  • min $1,470/wk
  • max $2,100/wk
  • min $1,323/wk
  • max $1,890/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $210 when you book by Sep-20-2019**
" 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 $123 Photo of Tuscany Vacation Rental Agritourism
  • min $961/wk
  • max $1,230/wk
  • min $865/wk
  • max $1,107/wk
  • Min Stay: 4 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $123 when you book by Sep-20-2019**
" Wonderful...." - Fred
Save $401 Photo of House Rental in Tuscany, Buonconvento
  • min $1,882/wk
  • max $4,013/wk
  • min $1,694/wk
  • max $3,612/wk
  • Min Stay: 7 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $401 when you book by Sep-20-2019**
Save $221 Photo of Apartment within a Villa in Southern Tuscany
  • min $2,059/wk
  • max $2,206/wk
  • min $1,853/wk
  • max $1,985/wk
  • Min Stay: 7 days
Sleeps 3 to 5 people
  • 1 single bedrooms
  • 1 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $221 when you book by Sep-20-2019**
" Amazing! Staying here was like being in paradise. ..." - Cassandra
Save $759 Photo of Tuscany Villa near Siena with Private Pool
  • min $3,338/wk
  • max $7,587/wk
  • min $3,004/wk
  • max $6,828/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 $759 when you book by Sep-20-2019**
" 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 $706 Photo of Villa Rental in Tuscany, Montalcino
  • min $6,174/wk
  • max $7,056/wk
  • min $5,557/wk
  • max $6,350/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 $706 when you book by Sep-20-2019**
Save $670 Photo of Sophisticated Villa in a Village in Southern Tuscany
  • min $4,000/wk
  • max $6,700/wk
  • min $3,600/wk
  • max $6,030/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 2 single bedrooms
  • 3 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $670 when you book by Sep-20-2019**
Save $205 Photo of Farmhouse Rental in Tuscany, San Giovanni
  • min $1,067/wk
  • max $2,049/wk
  • min $960/wk
  • max $1,844/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 $205 when you book by Sep-20-2019**
Save $411 Photo of Farmhouse in Southern Tuscany with Pool
  • min $2,276/wk
  • max $4,114/wk
  • min $2,048/wk
  • max $3,703/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 $411 when you book by Sep-20-2019**
" The view was great. ..." - Charlotte
Save $588 Photo of Charming Villa with Pool in Tuscany
  • min $2,801/wk
  • max $5,881/wk
  • min $2,521/wk
  • max $5,293/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 $588 when you book by Sep-20-2019**
" Very Good. A little too far from grocery store and Florence...." - Mary
Save $305 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $1,401/wk
  • max $3,046/wk
  • min $1,261/wk
  • max $2,741/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $305 when you book by Sep-20-2019**
" 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 $181 Photo of Vacation Rental Agritourism in Tuscany
  • min $1,520/wk
  • max $1,814/wk
  • min $1,368/wk
  • max $1,633/wk
  • Min Stay: 4 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $181 when you book by Sep-20-2019**
" A wonderful place to relax...." - Ruth
Save $124 Photo of House Rental in Tuscany, Siena
  • min $1,155/wk
  • max $1,239/wk
  • min $1,040/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 Sep-20-2019**
Save $3,851 Photo of Large Estate with Historic Villa and Two Farmhouses for a Large Group
  • min $31,242/wk
  • max $38,505/wk
  • min $28,118/wk
  • max $34,655/wk
  • Min Stay: 3 days
Sleeps 38 people
  • 19 double bedrooms
  • 15 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $3,851 when you book by Sep-20-2019**
" The historical impact of the villa made it magical. ..." - Mike
Save $257 Photo of Family-Friendly Farmhouse Close to Siena
  • min $1,338/wk
  • max $2,573/wk
  • min $1,204/wk
  • max $2,316/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $257 when you book by Sep-20-2019**
" The view of the hills, grape orchard, and olive trees...." - Ann
Save $414 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $1,909/wk
  • max $4,142/wk
  • min $1,718/wk
  • max $3,728/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 $414 when you book by Sep-20-2019**
" Very nice and restful. S..." - Olenka
 
Displaying 1 to 30 of 99 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..