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South Florence Villas and Vacation 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 31 to 60 of 170 villas
  • min $1,357/wk
  • max $2,017/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $1,190/wk
  • max $1,890/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • min $1,471/wk
  • max $2,059/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Maid Service
" 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 $1,785/wk
  • max $8,777/wk
  • Min Stay: 7 days
Sleeps 15 people
  • 1 single bedrooms
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" We enjoyed having all the space we needed for our large group. We loved sitting by the pool and enjoying the view. We cooked out at the grill and ate breakfast ..." - Beverly
  • min $1,119/wk
  • max $1,601/wk
  • Min Stay: 7 days
Sleeps 3 people
  • 1 single bedrooms
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" We loved this place. We loved the beauty, areas to walk, small town nearby, great local restaurants and convenience to cities...." - Linda
  • min $755/wk
  • max $1,286/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $622/wk
  • max $1,263/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $834/wk
  • max $1,079/wk
  • Min Stay: 7 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
  • min $692/wk
  • max $1,134/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Ambiance. Staff was very good...." - Will
  • min $4,901/wk
  • max $9,102/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Overall experience was wonderful. Gabriella, the manager, was well-informed and provided great insight as to local restaurants, local markets, local stores and tr..." - Dorothy
  • 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 $1,226/wk
  • max $1,667/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
" It was a beautiful property and the staff was exceptional especially helping us through a difficult situation we encountered. We would return!..." - Kim
  • min $1,289/wk
  • max $2,483/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Very good. Owners were very accessible and accommodating. The vendemmia (grape harvest) was on at the time in their fields and they invited us to see the harvest a..." - Fran
  • $1,458/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 2 bathrooms
  • Washing Machine
  • Maid Service
  • Air Conditioning
" The restoration is very good quality. Most of the furnishings are Ikea so they are functional and attractive. Antiques and paintings add to the atmosphere of the p..." - Allan
  • min $4,480/wk
  • max $6,335/wk
  • Min Stay: 7 days
Sleeps 12 to 15 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • min $8,978/wk
  • max $12,628/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
  • min $910/wk
  • max $1,655/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $777/wk
  • max $1,263/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" 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
  • min $700/wk
  • max $1,655/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" 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
  • min $1,372/wk
  • max $1,960/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
  • 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
" WONDERFUL! Sonia (manager) was very helpful and attentive. The property is beautiful, spacious and in a great location. We loved every minute and would like to hav..." - Carol
  • min $2,002/wk
  • max $2,485/wk
  • Min Stay: 7 days
Sleeps 3 to 5 people
  • 1 single bedrooms
  • 1 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" The villa was very nice. Spacious and well appointed. The setting was beautiful. The villa itself was very close to a road that took some getting used to...." - alan
  • min $13,108/wk
  • max $20,214/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
  • min $1,297/wk
  • max $1,920/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" It was great!..." - Jennifer
  • min $1,226/wk
  • max $1,667/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Pure heaven! The place was beautifully restored and decorated, the setting was perfect, the staff were incredibly helpful and nice. We couldn't have asked for..." - Dana
  • min $3,316/wk
  • max $4,596/wk
  • Min Stay: 7 days
Sleeps 8 to 10 people
  • 4 double bedrooms
  • 5 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Great Villa to rent. We took the entire main house, which can be subdivided into three units. There were two kitchens in the house, and they were able to accomodat..." - Lloyd
  • 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 $1,904/wk
  • max $2,891/wk
  • Min Stay: 3 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Our experience surpassed our expectation. The property is charming, beautiful, spacious and is more beautiful than the online brochure. The house itself was also c..." - Chris
  • min $1,357/wk
  • max $2,017/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" It was truly the best experience. everything was wonderful. Couldn't have ask for a more peaceful vacation...." - Christina
  • min $1,120/wk
  • max $2,660/wk
  • Min Stay: 3 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
 
Displaying 31 to 60 of 170 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..