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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 91 to 120 of 168 villas
  • min $812/wk
  • max $1,655/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $18,046/wk
  • max $24,808/wk
  • Min Stay: 7 days
Sleeps 50 people
  • 25 double bedrooms
  • 25 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
  • min $1,316/wk
  • max $1,792/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
  • min $11,639/wk
  • max $15,927/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" The property was better than our lofty expectations. We were treated warmly and everything that was done for us and our family and guests exceeded our imagination..." - Ken
  • min $1,681/wk
  • max $1,961/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" We had a wonderful week at Certaldo 4. The villa was lovely, comfortable and immaculate. The grounds are beautifully landscaped and maintained. Sylvia, the prop..." - Janice
  • min $1,120/wk
  • max $2,660/wk
  • Min Stay: 7 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 $1,785/wk
  • max $8,174/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 $8,588/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
" 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
  • min $4,481/wk
  • max $9,708/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Our experience at Villa Pucci was absolute perfection! The house and view are spectacular. ..." - Amy
Save $2,398 Photo of Beautiful Tuscan Villa on a Large Estate
  • min $9,590/wk
  • max $15,680/wk
  • min $7,193/wk
  • Min Stay: 7 days
Sleeps 22 people
  • 11 double bedrooms
  • 11 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $2,398 when you book by Feb-28-2018**
" Wonderful...." - Naomi
  • min $1,681/wk
  • max $1,961/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
  • min $700/wk
  • max $1,540/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $812/wk
  • max $1,655/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $771/wk
  • max $1,541/wk
  • Min Stay: 7 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Fantastic place with beautiful views, very secluded and quiet. Great and very large covered outdoor patio...." - Liz
  • min $1,148/wk
  • max $2,154/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Good...." - Randee
  • min $700/wk
  • max $1,540/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Wonderful. A magnificent building in beautiful countryside. We rented 5 units - all in the out-buildings. I entered the same comments for all 5 units. ..." - Michael
  • min $1,260/wk
  • max $2,450/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $1,316/wk
  • max $1,792/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $791/wk
  • max $1,701/wk
  • Min Stay: 7 days
Sleeps 5 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $840/wk
  • max $1,820/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" It was comfortable, clean, and conveniently located. ..." - Misty
  • min $1,625/wk
  • max $3,081/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Excellent. Beautiful house and property...." - Gary
  • min $2,651/wk
  • max $5,041/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Amazing!! From the moment we arrived it felt like heaven on earth. The villa is beautiful. We had plenty of room and the facilities were immaculate. The pool was t..." - Nichola
  • min $1,888/wk
  • max $3,235/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Good quiet location, comfortable beds, well appointed house and gracious host. Glad it had a washing machine, dryer and clothes line...." - Gail
  • min $2,084/wk
  • max $3,603/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Beautiful views of the countryside. Very Tuscan rural villa. Quiet and restful place...." - Genevieve
  • min $630/wk
  • max $1,192/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • 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 $5,601/wk
  • max $7,841/wk
  • Min Stay: 5 days
Sleeps 14 people
  • 2 single bedrooms
  • 9 double bedrooms
  • 11 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
" 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
  • min $1,000/wk
  • max $3,235/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" We had a wonderful time. It was central to many things we wanted to see and do. Elizabeth was a great host. ..." - Joe
  • min $812/wk
  • max $1,120/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
  • min $700/wk
  • max $1,540/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Wonderful. A magnificent castle with out-buildings in beautiful countryside. We rented 5 units - all in the out-buildings. I entered the same comments for all 5 ..." - Michael
 
Displaying 91 to 120 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..