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 83 villas
Save $990 Photo of Villa on Large Estate Near San Gimignano
  • min $8,300/wk
  • max $9,900/wk
  • min $7,470/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 Jun-10-2023**
" Fantastic - Sandro and Nelson were excellent hosts...." - Peggy
Save $1,068 Photo of Cozy Tuscan Villa near Montepulciano
  • min $5,951/wk
  • max $10,677/wk
  • min $5,356/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 Jun-10-2023**
" 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
  • Enquire for Rates
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
" 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 $3,501 Photo of Estate Rental in Tuscany, Gaiole in Chianti (Chianti Area)
  • $35,005/wk
  • $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 Jun-10-2023**
Save $245 Photo of Tuscany Villa Rental
  • min $1,640/wk
  • max $2,449/wk
  • min $1,476/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 Jun-10-2023**
" 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 $1,008 Photo of Villa Rental in Tuscany, Monticchiello
  • min $5,181/wk
  • max $10,082/wk
  • min $4,663/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 Jun-10-2023**
  • Enquire for Rates
Sleeps 38 people
  • 19 double bedrooms
  • 15 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" The historical impact of the villa made it magical. ..." - Mike
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 Jun-10-2023**
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 Jun-10-2023**
  • Enquire for Rates
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
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 Jun-10-2023**
" A wonderful experience at the villa...." - John
  • Enquire for Rates
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" 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 $1,009 Photo of Beautiful Farmhouse in the Chianti Near Town
  • min $6,483/wk
  • max $10,092/wk
  • min $5,835/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 Jun-10-2023**
" The property itself was very pretty with amazing views. It was centrally located and fairly easy to access. ..." - Jacqueline
  • 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
  • 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
  • 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 $474 Photo of Farmhouse Rental in Chianti Area of Tuscany
  • $4,744/wk
  • $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 Jun-10-2023**
" 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
  • Enquire for Rates
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" 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 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
Save $1,428 Photo of Rustic Countryside Villa with Pool near San Casciano dei Bagni
  • min $8,962/wk
  • max $14,282/wk
  • min $8,066/wk
  • max $12,854/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,428 when you book by Jun-10-2023**
" Wonderful - We stayed at Villa Orcia with 10 adults and there was plenty of room for everyone. Patrizia is extremely helpful...." - Renee
  • Enquire for Rates
Sleeps 16 people
  • 8 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
Save $219 Photo of Country Villa in heart of Chianti centrally located close to regions’ history, art, restaurants.
  • min $1,469/wk
  • max $2,193/wk
  • min $1,322/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 Jun-10-2023**
" 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 $864 Photo of Villa Rental in Tuscany, Montalcino
  • min $8,134/wk
  • max $8,636/wk
  • min $7,321/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 Jun-10-2023**
  • 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
  • Enquire for Rates
Sleeps 2 to 4 people
  • 1 bathrooms
  • Independent House
  • Maid Service
  • Air Conditioning
Save $412 Photo of House Rental in Tuscany, Buonconvento
  • min $2,159/wk
  • max $4,117/wk
  • min $1,943/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 Jun-10-2023**
  • Enquire for Rates
Sleeps 12 people
  • 7 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
  • Enquire for Rates
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
  • Enquire for Rates
Sleeps 2 to 6 people
  • 1 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
  • Enquire for Rates
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
 
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..