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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 >

Showing 1 to 30 of 168 properties
Save $438 Photo of Villa Rental Chianti Tuscany Near Florence
  • min $2,190/wk
  • max $4,130/wk
  • min $1,752/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 $438 when you book by Nov-30-2017**
" It was fantastic and everything I hoped it would be. The villa is beautiful and looks exactly as the pictures show it. The setting is spectacular and looking out..." - Lucy
Save $944 Photo of Villa in Tuscany Near Certaldo and the Chianti Region
  • min $1,888/wk
  • max $3,235/wk
  • min $1,227/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $944 when you book by Nov-30-2017**
" Good quiet location, comfortable beds, well appointed house and gracious host. Glad it had a washing machine, dryer and clothes line...." - Gail
  • min $1,908/wk
  • max $2,820/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" Our stay was wonderful. The villa is beautiful inside and out. It is surrounded by olive groves and vineyards. The hosts Emma, Giancarlo, and Matteo greeted us at..." - Carolyn
Save $441 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $1,471/wk
  • max $2,573/wk
  • min $1,030/wk
  • Min Stay: 7 days
Sleeps 4 to 7 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $441 when you book by Nov-30-2017**
" This was a perfect holiday location to experience the delights of Tuscany...." - Prudence
Save $1,081 Photo of Family-Friendly Villa Rental in Tuscany with Pool
  • min $2,084/wk
  • max $3,603/wk
  • min $1,355/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,081 when you book by Nov-30-2017**
" Beautiful views of the countryside. Very Tuscan rural villa. Quiet and restful place...." - Genevieve
  • min $2,940/wk
  • max $5,250/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Excellent..." - Monica
Save $944 Photo of Tuscany Villa Rental in Chianti
  • min $1,000/wk
  • max $3,235/wk
  • min $650/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $944 when you book by Nov-30-2017**
" We had a wonderful time. It was central to many things we wanted to see and do. Elizabeth was a great host. ..." - Joe
  • min $2,311/wk
  • max $4,761/wk
  • Min Stay: 3 days
Sleeps 16 to 17 people
  • 8 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Our overall experience was very positive. We had a great time whether we were relaxing by the villa or exploring a city or town on a day trip. The villa offers p..." - Lynne
  • min $615/wk
  • max $2,614/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" Outstanding and memorable experience for all of us...." - Bruce
Save $2,352 Photo of Beautiful Large Villa Close to Florence
  • min $5,601/wk
  • max $7,841/wk
  • min $5,489/wk
  • Min Stay: 5 days
Sleeps 14 people
  • 2 single bedrooms
  • 9 double bedrooms
  • 11 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $2,352 when you book by Nov-30-2017**
" It was perfect and wonderful - peaceful, relaxing the villa suited our needs perfectly. The owner was wonderful and accommodating and the property was in excellent..." - Laura
Save $2,912 Photo of Large Villa Rental in Tuscany Near Florence with Pool
  • min $6,721/wk
  • max $9,708/wk
  • Min Stay: 5 days
Sleeps 20 people
  • 2 single bedrooms
  • 9 double bedrooms
  • 11 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $2,912 when you book by Nov-30-2017**
" A wonderful two weeks was thoroughly enjoyed by our entire family of 20 people aged from 4 years up to 70 years. Facilities were excellent in every respect and ass..." - Terry
Save $2,877 Photo of Beautiful Tuscan Villa on a Large Estate
  • min $9,590/wk
  • max $15,680/wk
  • min $6,713/wk
  • Min Stay: 7 days
Sleeps 22 people
  • 11 double bedrooms
  • 11 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $2,877 when you book by Nov-30-2017**
" Wonderful...." - Naomi
  • min $771/wk
  • max $1,541/wk
  • Min Stay: 7 days
Sleeps 5 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" It was an amazing vacation with our family in this beautiful setting. Our host Leonardo was extremely gracious and very accommodating...." - Diana
  • min $953/wk
  • max $1,550/wk
  • Min Stay: 7 days
Sleeps 5 to 6 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Location was terrific. We loved being able to walk to a market, wine shop, several restaurants, coffee cafes, and historical points. Hostess was exceptionally resp..." - Maryann
  • min $1,423/wk
  • max $5,601/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" I felt as if I was in a movie set...very scenic, peaceful and comfortable!..." - Derek
Save $309 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $1,030/wk
  • max $1,493/wk
  • min $721/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $309 when you book by Nov-30-2017**
" Fantastic!..." - Sam
  • min $1,961/wk
  • max $4,947/wk
  • Min Stay: 7 days
Sleeps 10 to 12 people
  • 5 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Fabulous...." - Tom
Save $441 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $1,471/wk
  • max $2,162/wk
  • min $1,030/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Maid Service
** Save up to $441 when you book by Nov-30-2017**
" My wife and I had a wonderful stay at Machiavelli. The grounds and view of the countryside were exquisite. Our villa was a great mix of old world charm and modern ..." - Aaron
  • min $1,401/wk
  • max $1,625/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" One of our favourite areas on our month-long trip in Italy. After staying in Florence this was such a pleasant, quiet week with gorgeous scenery, pool and friendl..." - Susan
  • min $1,680/wk
  • max $2,450/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
" We loved everything about our stay. Three couples stayed in Poggio 2. We were very comfortable--the 3 bedroom, 3 bath apartment was perfect. It was quiet and p..." - Mary
Save $859 Photo of Villa in Tuscany Near Certaldo and the Chianti Region
  • min $1,780/wk
  • max $2,945/wk
  • min $1,157/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $859 when you book by Nov-30-2017**
" Fantastic, better than our high expectations!..." - Harri
  • min $771/wk
  • max $1,541/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Delightful! We had come from Paris. Lucolena was the perfect contrast to a busy city. Loved the villa. We enjoyed the nearby towns, Greve and Dudda. We enjoye..." - Dennis
  • min $1,120/wk
  • max $2,660/wk
  • Min Stay: 4 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" This location is perfectly situated for all the day trips we had planned, from Cinque Terre to Siena. ..." - Sadia
  • min $11,375/wk
  • max $17,325/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" What a lovely villa! The location was perfect to get away from the crowds of Florence. Such a beautiful setting amongst the olive trees and vineyards nearby...." - Cyndi
  • $4,855/wk
  • Min Stay: 7 days
Sleeps 6 to 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
  • min $3,115/wk
  • max $5,320/wk
  • Min Stay: 7 days
Sleeps 10 to 12 people
  • 5 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" The villa is beautiful and very clean. The gardens are beautifully kept and the pool and surroundings are lovely...." - Jan
  • min $1,541/wk
  • max $2,666/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
  • Air Conditioning
" It was wonderful. ..." - Cathie
Save $250 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $834/wk
  • max $1,174/wk
  • min $584/wk
  • Min Stay: 7 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
** Save up to $250 when you book by Nov-30-2017**
Save $368 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $1,226/wk
  • max $1,814/wk
  • min $858/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
** Save up to $368 when you book by Nov-30-2017**
" Very nice...." - Marty
Save $250 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $834/wk
  • max $1,174/wk
  • min $584/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
** Save up to $250 when you book by Nov-30-2017**
" Very unique and attractive...." - Jorge
 
Showing 1 to 30 of 168 properties

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. With so much to do in the area, everyone in your group will love the area. View our Rental Villas in South Florence..