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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 168 villas
  • min $2,190/wk
  • max $4,130/wk
  • Min Stay: 3 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" 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
  • 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 Dec-24-2017**
" This was a perfect holiday location to experience the delights of Tuscany...." - Prudence
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 Dec-24-2017**
" 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 $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 Dec-24-2017**
" We had a wonderful time. It was central to many things we wanted to see and do. Elizabeth was a great host. ..." - Joe
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 Dec-24-2017**
" Good quiet location, comfortable beds, well appointed house and gracious host. Glad it had a washing machine, dryer and clothes line...." - Gail
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 Dec-24-2017**
" 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
  • 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
  • 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
  • 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 $1,423/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
  • 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 $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
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 Dec-24-2017**
" Fantastic, better than our high expectations!..." - Harri
  • 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
  • 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
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 Dec-24-2017**
" Fantastic!..." - Sam
  • 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 $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 Dec-24-2017**
" 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 $966/wk
  • max $1,232/wk
  • Min Stay: 5 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" It was the most wonderful place. So very near Firenze and yet in the quiet and lovely countryside. The administrator was very helpful and charming. We enjoy every ..." - Susana
  • 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
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 Dec-24-2017**
" Wonderful...." - Naomi
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 Dec-24-2017**
  • 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
  • min $771/wk
  • max $1,541/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" A wonderful place to relax after travelling non stop for a couple of weeks. A chance to unpack and spread out in such a beautiful part of the world. The refurbishm..." - Murray
  • min $1,718/wk
  • max $2,820/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" We had a wonderful 2 weeks with friends and family and would love to return again. This vacation was among the best ever...." - Jan
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 Dec-24-2017**
" It was SO beautiful and enchanting staying up in the Tuscan hills in a 9th century castle. Everyone was so friendly and helpful and the views from our windows wer..." - Linda
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 Dec-24-2017**
" Very nice...." - Marty
  • min $13,314/wk
  • max $20,358/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Wonderful...." - Jackie
 
Displaying 1 to 30 of 168 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. With so much to do in the area, everyone in your group will love the area. View our Rental Villas in South Florence..