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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 61 to 90 of 168 villas
  • min $2,940/wk
  • max $6,440/wk
  • Min Stay: 7 days
Sleeps 16 to 18 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Our stay at Casa de Signa was tremendous. It is a farm house that once processed olive oil from orchards right on the property. We celebrated our 30th anniversa..." - Veronica
  • min $700/wk
  • max $1,470/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $622/wk
  • max $1,263/wk
  • Min Stay: 7 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 $1,961/wk
  • max $4,481/wk
  • Min Stay: 7 days
Sleeps 8 to 10 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Outstanding! The villa was even better than it looked in the pictures on the website. Check in was very easy and staff were very helpful in answering any questions..." - Julie
  • min $1,319/wk
  • max $2,368/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • $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 $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 $812/wk
  • max $1,120/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
  • min $812/wk
  • max $1,120/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
  • min $713/wk
  • max $1,588/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $1,372/wk
  • max $1,876/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
  • min $553/wk
  • max $1,134/wk
  • Min Stay: 7 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Ambiance. Staff was very good...." - Will
  • min $1,372/wk
  • max $1,876/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
  • min $1,185/wk
  • max $2,294/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $873/wk
  • max $1,704/wk
  • Min Stay: 7 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Very good. However, it was 104 most days and didn't cool off much at night. Good home base for day trips...." - Kelly
  • min $1,108/wk
  • max $2,331/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Our family very much enjoyed the owners' warm hospitality. They were very accommodating. The view is wonderful and the location is peaceful. ..." - Taylor
  • 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 $622/wk
  • max $1,263/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" We had a delightful time at the castle. The apartment was lovely and well maintained. The castle was very scenic...." - Joan
  • 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 $532/wk
  • max $1,120/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $4,541/wk
  • max $4,928/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
Save $1,733 Photo of Traditional Tuscan Villa on a Large Estate
  • min $6,930/wk
  • max $10,920/wk
  • min $5,198/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,733 when you book by Feb-28-2018**
" Wonderful...." - Dick
  • min $745/wk
  • max $1,494/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" 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
  • 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 $685/wk
  • max $1,315/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $4,138/wk
  • max $11,055/wk
  • Min Stay: 7 days
Sleeps 8 to 10 people
  • 2 single bedrooms
  • 4 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
" Once in a lifetime experience...." - Tom
  • min $812/wk
  • max $1,655/wk
  • Min Stay: 7 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" We absolutely loved our time at Il Castello 27! Our family loved the property and the people that worked there were so friendly and helpful!..." - Sharon
  • min $966/wk
  • max $1,344/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
  • min $1,372/wk
  • max $1,876/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 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
 
Displaying 61 to 90 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..