Suitcase

Your Suitcase contains your favorite villas and details of your upcoming trip. Sign up to use this feature.
Rated Excellent By Trip Advisor

Quick Filter

Travelers
Arrival Date
Departure Date
Max Price per Week

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 91 villas
Save $2,580 Photo of Villa on Large Estate Near San Gimignano
  • min $5,653/wk
  • max $9,300/wk
  • min $5,088/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 Feb-20-2020**
" 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 $1,225 Photo of Cozy Tuscan Villa near Montepulciano
  • min $5,041/wk
  • max $12,252/wk
  • min $4,537/wk
  • max $11,027/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 $1,225 when you book by Feb-20-2020**
" 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 $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 Feb-20-2020**
" Very good...." - Kenneth
Save $1,390 Photo of Spacious and Beautiful Tuscany Villa Near Montalcino
  • min $8,435/wk
  • max $13,895/wk
  • min $7,592/wk
  • max $12,506/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,390 when you book by Feb-20-2020**
" 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 $196 Photo of Restored Farmhouse Surrounded by Vineyards and Olive Groves, Centrally Located in Tuscany
  • min $1,513/wk
  • max $1,961/wk
  • min $1,362/wk
  • max $1,765/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $196 when you book by Feb-20-2020**
" Great. Claudia and Rudi terrific ..." - Frank
Save $198 Photo of Country Villa in heart of Chianti centrally located close to regions’ history, art, restaurants.
  • min $840/wk
  • max $1,980/wk
  • min $756/wk
  • max $1,782/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 $198 when you book by Feb-20-2020**
" 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 $380 Photo of Apartment Rental in the Center of Siena
  • min $2,450/wk
  • max $3,799/wk
  • min $2,205/wk
  • max $3,419/wk
  • Min Stay: 3 days
Sleeps 5 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $380 when you book by Feb-20-2020**
" Very good. The property was well located. ..." - Rick
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 Feb-20-2020**
" 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 $1,260 Photo of Beautiful Chianti Villa with Guest Cottage and Private Infinity Pool
  • min $9,522/wk
  • max $12,602/wk
  • min $8,570/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 Feb-20-2020**
" It was fantastic. ..." - Jessica
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 Feb-20-2020**
" Absolutely excellent. ..." - Kerby
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 Feb-20-2020**
" Wonderful...." - Fred
Save $157 Photo of Family-Friendly Apartment Close to Siena
  • min $1,030/wk
  • max $1,565/wk
  • min $927/wk
  • max $1,409/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $157 when you book by Feb-20-2020**
" The time spent at Terra di Siena was wonderful and I would go back in a heartbeat...." - Vallerie
Save $962 Photo of Rustic Tuscan Villa Surrounded by Olive Groves and Vineyards
  • $9,615/wk
  • $8,654/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $962 when you book by Feb-20-2020**
" 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
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 Feb-20-2020**
" 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 $118 Photo of Tuscany Holiday Apartment
  • 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 Feb-20-2020**
" Absolutely wonderful. Experience enhanced by the warm hospitality of Claudia and Rudy - we left feeling like family friends not hospitality guests...." - Kay
Save $706 Photo of Villa Rental in Tuscany, Montalcino
  • min $6,419/wk
  • max $7,056/wk
  • min $5,777/wk
  • max $6,350/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 $706 when you book by Feb-20-2020**
Save $1,033 Photo of Tuscan Farmhouse with Private Pool and Beautiful Views
  • min $7,350/wk
  • max $10,325/wk
  • min $6,615/wk
  • max $9,293/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,033 when you book by Feb-20-2020**
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 Feb-20-2020**
" The view of the hills, grape orchard, and olive trees...." - Ann
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 Feb-20-2020**
" Wonderful - We stayed at Villa Orcia with 10 adults and there was plenty of room for everyone. Patrizia is extremely helpful...." - Renee
Save $151 Photo of Vacation Rental Agritourism in Tuscany
  • min $1,345/wk
  • max $1,513/wk
  • min $1,211/wk
  • max $1,362/wk
  • Min Stay: 4 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $151 when you book by Feb-20-2020**
" A wonderful place to relax...." - Ruth
Save $123 Photo of Farmhouse Accommodation in Tuscany
  • 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 Feb-20-2020**
" Beautiful stay...." - Joan
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 Feb-20-2020**
" Very Good. A little too far from grocery store and Florence...." - Mary
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 Feb-20-2020**
" 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 $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 Feb-20-2020**
" Our 4 weeks at Villa Brunello were everything we could have dreamed and more! The PERFECT Tuscan experience in every way!..." - Matt
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 Feb-20-2020**
" We loved this experience! We were there for 2 weeks in August and had different groups of people coming to stay with us. The property is part of a working farm (..." - Marty
Save $291 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,689/wk
  • max $2,913/wk
  • min $1,520/wk
  • max $2,622/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $291 when you book by Feb-20-2020**
" Amazing! We felt like we were part of a family on the property - Sandra, Nicolo, and all the staff were so friendly and helpful. The whole experience made us fee..." - Rayna
Save $1,909 Photo of Farmhouse in the Chianti Region for Friends or a Large Family
  • max $8,663/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 $1,909 when you book by Feb-20-2020**
" 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 $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 Feb-20-2020**
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 Feb-20-2020**
" 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 $2,007 Photo of Villa Rental in Tuscany, Buonconvento
  • min $15,389/wk
  • max $20,065/wk
  • min $13,850/wk
  • max $18,059/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $2,007 when you book by Feb-20-2020**
 
Displaying 1 to 30 of 91 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..