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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 92 villas
Save $2,580 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 $2,580 when you book by Sep-30-2020**
" Villa Dora exceeded our expectations in every way! We were a family of 6 adults and every one of us fell in love with the villa!..." - Lynn
Save $1,058 Photo of Cozy Tuscan Villa near Montepulciano
  • min $5,041/wk
  • max $10,580/wk
  • min $4,537/wk
  • max $9,522/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 $1,058 when you book by Sep-30-2020**
" There were 13 of us, 8 adults and 5 children ages 6 to 10. All had a great time and there was plenty of room for all. The adults particularly enjoyed sitting on th..." - Michael
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-30-2020**
" 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 $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-30-2020**
" 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 $532 Photo of Chianti Tuscany Villa Rental, Near Siena
  • min $2,451/wk
  • max $5,321/wk
  • min $2,206/wk
  • max $4,789/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 $532 when you book by Sep-30-2020**
" Absolutely excellent. ..." - Kerby
Save $265 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $1,224/wk
  • max $2,654/wk
  • min $1,102/wk
  • max $2,389/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 $265 when you book by Sep-30-2020**
" 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 $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 Sep-30-2020**
" 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 $404 Photo of Farmhouse Rental in Tuscany, Montalcino
  • min $2,399/wk
  • max $4,039/wk
  • min $2,159/wk
  • max $3,635/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 $404 when you book by Sep-30-2020**
" Very cozy property, although a tiny kitchen for a property of that size...." - Anne
Save $581 Photo of Charming Villa with Pool in Tuscany
  • min $2,801/wk
  • max $5,811/wk
  • min $2,521/wk
  • max $5,230/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 $581 when you book by Sep-30-2020**
" Very Good. A little too far from grocery store and Florence...." - Mary
Save $866 Photo of Farmhouse in the Chianti Region for Friends or a Large Family
  • min $4,323/wk
  • max $8,663/wk
  • min $3,891/wk
  • max $7,797/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 Sep-30-2020**
" 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 $108 Photo of Tuscany Holiday Apartment
  • 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 Sep-30-2020**
" Absolutely wonderful. Experience enhanced by the warm hospitality of Claudia and Rudy - we left feeling like family friends not hospitality guests...." - Kay
Save $1,582 Photo of Villa Rental in Tuscany, Castelnuova Berardenga
  • min $11,599/wk
  • max $15,820/wk
  • min $10,439/wk
  • max $14,238/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
** Save up to $1,582 when you book by Sep-30-2020**
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-30-2020**
" 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 $3,466 Photo of Large Estate with Historic Villa and Two Farmhouses for a Large Group
  • $34,655/wk
  • $31,190/wk
  • Min Stay: 3 days
Sleeps 38 people
  • 19 double bedrooms
  • 15 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $3,466 when you book by Sep-30-2020**
" The historical impact of the villa made it magical. ..." - Mike
Save $237 Photo of Farmhouse Rental in Tuscany, San Giovanni
  • min $1,067/wk
  • max $2,372/wk
  • min $960/wk
  • max $2,135/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 $237 when you book by Sep-30-2020**
Save $734 Photo of Villa Rental in Tuscany, Montalcino
  • min $6,419/wk
  • max $7,341/wk
  • min $5,777/wk
  • max $6,607/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 $734 when you book by Sep-30-2020**
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-30-2020**
" 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 $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-30-2020**
" Very nice and restful. S..." - Olenka
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-30-2020**
" The view was great. ..." - Charlotte
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-30-2020**
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 Sep-30-2020**
" Our 4 weeks at Villa Brunello were everything we could have dreamed and more! The PERFECT Tuscan experience in every way!..." - Matt
Save $4,852 Photo of Villa Rental in Tuscany, Montepulciano
  • min $30,874/wk
  • max $48,516/wk
  • min $27,787/wk
  • max $43,664/wk
  • Min Stay: 4 days
Sleeps 24 people
  • 12 double bedrooms
  • 12 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
** Save up to $4,852 when you book by Sep-30-2020**
Save $401 Photo of House Rental in Tuscany, Buonconvento
  • min $1,881/wk
  • max $4,013/wk
  • min $1,693/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-30-2020**
Save $956 Photo of Chianti Villa near a Charming Village
  • min $1,129/wk
  • max $9,557/wk
  • min $1,016/wk
  • max $8,601/wk
  • Min Stay: 3 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $956 when you book by Sep-30-2020**
" Great experience in a spectacular villa...." - Viviane
Save $1,765 Photo of Villa Rental in Tuscany, Buonconvento
  • min $10,086/wk
  • max $17,651/wk
  • min $9,077/wk
  • max $15,886/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,765 when you book by Sep-30-2020**
Save $1,151 Photo of Tuscan farmhouse with pool a rural retreat in the Crete Senesi near Siena
  • min $5,228/wk
  • max $11,506/wk
  • min $4,705/wk
  • max $10,355/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,151 when you book by Sep-30-2020**
Save $235 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,672/wk
  • max $2,353/wk
  • min $1,505/wk
  • max $2,118/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $235 when you book by Sep-30-2020**
" Tuscany at its best, staff treated us like family and the villa was outstanding...." - Buster
Save $137 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $976/wk
  • max $1,373/wk
  • min $878/wk
  • max $1,236/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $137 when you book by Sep-30-2020**
" It was amazing. Everything was very well done...." - Simin
Save $167 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,168/wk
  • max $1,667/wk
  • min $1,051/wk
  • max $1,500/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $167 when you book by Sep-30-2020**
" A wonderful experience. We'd definitely go again but would probably choose an apartment at the villa with more windows. ..." - Margaret
Save $177 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,248/wk
  • max $1,765/wk
  • min $1,123/wk
  • max $1,589/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $177 when you book by Sep-30-2020**
" Wonderful!..." - Peter
 
Displaying 1 to 30 of 92 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..