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Vacation Accommodation Chianti Tuscany Villa Rentals

South of Florence lies the Chianti, Italy's definitive wine-growing region. This area boasts hills covered in vineyards, winding roads (favored by sporty drivers and daredevil cyclists), and breathtaking vistas.   Continue >

Displaying 1 to 30 of 132 villas
  • min $5,617/wk
  • max $9,350/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" Very relaxing, peaceful, in a beautiful setting. ..." - Louise
Save $507 Photo of Farmhouse Rental Near Certaldo, Tuscany
  • min $2,573/wk
  • max $5,070/wk
  • min $2,316/wk
  • max $4,563/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $507 when you book by Jun-30-2022**
" We enjoyed it very much. We have been to Tuscany several times and we were very pleased with everything at Donatella. When we arrived there was a welcome basket of..." - Bonnie
Save $710 Photo of Charming, traditional Tuscan villa with pool, terrace with views, located in Montaione
  • min $5,274/wk
  • max $7,098/wk
  • min $4,747/wk
  • max $6,388/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $710 when you book by Jun-30-2022**
" Fantastic. We love this place ..." - Linda
Save $455 Photo of Villa Rental Chianti Tuscany Near Florence
  • min $2,415/wk
  • max $4,554/wk
  • min $2,174/wk
  • max $4,099/wk
  • Min Stay: 3 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $455 when you book by Jun-30-2022**
" We had a wonderful time. The house was beautiful and everything we expected. ..." - Theresa
  • Enquire for Rates
Sleeps 80 to 120 people
  • 1 single bedrooms
  • 42 double bedrooms
  • 35 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
Save $183 Photo of CastleApartment Rental in Tuscany, Montespertoli (Chianti Area)
  • min $1,084/wk
  • max $1,829/wk
  • min $976/wk
  • max $1,646/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $183 when you book by Jun-30-2022**
Save $166 Photo of Tuscan Apartment in Historic Castle
  • min $801/wk
  • max $1,659/wk
  • min $721/wk
  • max $1,493/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $166 when you book by Jun-30-2022**
Save $904 Photo of Villa Rental in Tuscany, Montespertoli (Chianti Area)
  • min $7,303/wk
  • max $9,041/wk
  • min $6,573/wk
  • max $8,137/wk
  • Min Stay: 7 days
Sleeps 14 to 15 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $904 when you book by Jun-30-2022**
Save $637 Photo of Tuscany Villa on a Hill Close to Florence
  • min $4,411/wk
  • max $6,371/wk
  • min $3,970/wk
  • max $5,734/wk
  • Min Stay: 7 days
Sleeps 8 to 11 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $637 when you book by Jun-30-2022**
" Driving through the gates and to the property is absolutely lovely. The villa was extremely relaxing with a wonderful view and in a great location...." - Melissa
Save $181 Photo of Walk To Small Town for Cappuccino in Tuscany
  • min $928/wk
  • max $1,811/wk
  • min $835/wk
  • max $1,630/wk
  • Min Stay: 7 days
Sleeps 5 to 6 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $181 when you book by Jun-30-2022**
" It was an experience of a lifetime - just awesome!..." - Carmita
Save $208 Photo of Tuscan Apartment in Historic Castle
  • min $1,125/wk
  • max $2,077/wk
  • min $1,013/wk
  • max $1,869/wk
  • Min Stay: 3 days
Sleeps 2 to 5 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $208 when you book by Jun-30-2022**
" Terrific!..." - Ross
Save $329 Photo of Tuscany Villa with Private Pool
  • min $1,708/wk
  • max $3,290/wk
  • min $1,537/wk
  • max $2,961/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $329 when you book by Jun-30-2022**
" We loved this hunter's cottage! The property manager couldn't have been more helpful. The pool was a delight and the property was lovely with an eclectic a..." - Jane
Save $208 Photo of Tuscan Apartment in Historic Castle
  • min $1,179/wk
  • max $2,078/wk
  • min $1,061/wk
  • max $1,870/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $208 when you book by Jun-30-2022**
" Driving up to the Castle was a surreal experience. It looks like a castle from a story book. The frescoes were everywhere, including the entire room. It made fo..." - Lauren
Save $195 Photo of Tuscan Apartment in Historic Castle
  • min $887/wk
  • max $1,952/wk
  • min $798/wk
  • max $1,757/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $195 when you book by Jun-30-2022**
" We liked the gardens and the castle next door, the views of the country, and the quietness. We slept well, but in the summer it's warm, and there is no A/C. A ..." - Carlos
Save $214 Photo of Tuscan Apartment in Historic Castle
  • min $978/wk
  • max $2,144/wk
  • min $880/wk
  • max $1,930/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $214 when you book by Jun-30-2022**
Save $204 Photo of Tuscan Apartment in Historic Castle
  • min $887/wk
  • max $2,044/wk
  • min $798/wk
  • max $1,840/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $204 when you book by Jun-30-2022**
Save $1,100 Photo of Villa Rental in Tuscany, Impruneta
  • min $6,797/wk
  • max $10,997/wk
  • min $6,117/wk
  • max $9,897/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,100 when you book by Jun-30-2022**
" We had a wonderful stay..." - Lilli
Save $230 Photo of Tuscan Apartment in Historic Castle
  • min $1,287/wk
  • max $2,302/wk
  • min $1,158/wk
  • max $2,072/wk
  • Min Stay: 3 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $230 when you book by Jun-30-2022**
Save $205 Photo of Tuscan Apartment in Historic Castle
  • min $887/wk
  • max $2,050/wk
  • min $798/wk
  • max $1,845/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $205 when you book by Jun-30-2022**
" We'll be back...." - Tammy
Save $156 Photo of Tuscan Apartment in Historic Castle
  • min $675/wk
  • max $1,559/wk
  • min $608/wk
  • max $1,403/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $156 when you book by Jun-30-2022**
" Love this property. Second year in a row I have been there...." - Sadia
Save $176 Photo of Tuscan Apartment in Historic Castle
  • min $985/wk
  • max $1,755/wk
  • min $887/wk
  • max $1,580/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $176 when you book by Jun-30-2022**
" We loved everything about it, the architecture is wonderful, the grounds are like heaven. I would like to think the people-staff are the best, and we are going ba..." - Barbara
Save $136 Photo of Tuscan Apartment in Historic Castle
  • min $622/wk
  • max $1,364/wk
  • min $560/wk
  • max $1,228/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $136 when you book by Jun-30-2022**
Save $179 Photo of Tuscan Apartment in Historic Castle
  • min $1,126/wk
  • max $1,787/wk
  • min $1,013/wk
  • max $1,608/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $179 when you book by Jun-30-2022**
Save $176 Photo of Tuscan Apartment in Historic Castle
  • min $787/wk
  • max $1,757/wk
  • min $708/wk
  • max $1,581/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $176 when you book by Jun-30-2022**
Save $221 Photo of Tuscan Apartment in Historic Castle
  • min $903/wk
  • max $2,210/wk
  • min $813/wk
  • max $1,989/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $221 when you book by Jun-30-2022**
Save $1,785 Photo of Luxury Villa with Staff near Florence
  • min $12,451/wk
  • max $17,850/wk
  • min $11,206/wk
  • max $16,065/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,785 when you book by Jun-30-2022**
" The staff were excellent and the property was beautiful. We had a few issues with no water on the first night. The manager fixed the water issue very promptly. The..." - Treena
Save $215 Photo of Tuscan Apartment in Historic Castle
  • min $887/wk
  • max $2,145/wk
  • min $798/wk
  • max $1,931/wk
  • Min Stay: 3 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $215 when you book by Jun-30-2022**
" The location was very good. Easy driving to some of the towns we wanted to visit, such as Pisa, Lucca and Siena. The beds were comfortable and the villa was roomy..." - Cheryl
Save $167 Photo of Tuscan Apartment in Historic Castle
  • min $782/wk
  • max $1,673/wk
  • min $704/wk
  • max $1,506/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $167 when you book by Jun-30-2022**
" The castle is beautiful...." - Serena
Save $683 Photo of Two Chianti Farmhouses for Large Group on a Wine Estate
  • min $2,988/wk
  • max $6,826/wk
  • min $2,689/wk
  • max $6,143/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $683 when you book by Jun-30-2022**
" I don't think we even dreamed that staying at this villa would be the experience it turned into a truly once-in-a-lifetime experience when family could all com..." - Keith
Save $222 Photo of Tuscan Apartment in Historic Castle
  • min $887/wk
  • max $2,221/wk
  • min $798/wk
  • max $1,999/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $222 when you book by Jun-30-2022**
" We thoroughly enjoyed our stay and the property was very well-maintained. We would recommend staying here to others. We quickly realized, however, that some of the..." - Wendy
 
Displaying 1 to 30 of 132 villas

Following the old Chiantigiana road you see the heart of this region, including the northerly reaches of San Casciano and its environs and the Chianti Classico. What to do while in the Chianti? Eat, drink, and be merry. Towns like Panzano, Greve-in-Chianti, and Radda-in-Chianti---and all the wineries in between---are filled with gastronomic delights and a dizzying selection of wine shops. A wonderful place to bring your family or friends for an unforgettable Tuscan experience..