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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 121 to 150 of 170 villas
Save $1,593 Photo of Private Villa on a Castle Estate near Certaldo
  • 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
** Save up to $1,593 when you book by Jun-30-2018**
" 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 $840/wk
  • max $1,820/wk
  • Min Stay: 3 days
Sleeps 8 people
  • 4 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" It was comfortable, clean, and conveniently located. ..." - Misty
  • min $9,382/wk
  • max $17,643/wk
  • Min Stay: 7 days
Sleeps 13 to 14 people
  • 1 single bedrooms
  • 6 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" Villa Carmina is wonderful. There were 13 adults in our party and the villa easily accommodated a group of that size. ..." - Bruce
  • min $980/wk
  • max $2,819/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
  • min $3,613/wk
  • max $7,521/wk
  • Min Stay: 7 days
Sleeps 12 to 14 people
  • 6 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" It was awesome! And meeting Elizabeth and Adi, the owners, was a highlight! Loved them and hiking all over the property!..." - Anne
  • 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 $2,521/wk
  • max $4,015/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Very comfortable, beautiful home. Great owners who were very helpful to us. ..." - Bruna
  • min $1,435/wk
  • max $2,154/wk
  • Min Stay: 3 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Good...." - Randee
  • min $910/wk
  • max $2,030/wk
  • Min Stay: 3 days
Sleeps 8 people
  • 4 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" We loved it. We were 6 woman so we bought local fare and cooked in our big kitchen. ..." - Alice Celine
  • min $700/wk
  • max $1,540/wk
  • Min Stay: 3 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
  • $18,229/wk
  • Min Stay: 7 days
Sleeps 24 people
  • 12 double bedrooms
  • 12 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" We had the best time. All the family reunited and the times spent together for two weeks were priceless...." - Mindy
  • min $7,000/wk
  • max $8,750/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" Overall it was very good to excellent...." - Jill
  • min $700/wk
  • max $1,540/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Beautiful, large castle in a picture perfect location that seemed like something out of a Tuscan fantasy. ..." - Deborah
  • min $700/wk
  • max $1,470/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" We'll be back...." - Tammy
  • min $1,519/wk
  • max $3,079/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" In very good condition. A real retreat with a fantastic view..." - Andrew
  • 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 $8,555/wk
  • max $13,228/wk
  • Min Stay: 7 days
Sleeps 19 people
  • 1 single bedrooms
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" It was a wonderful place to stay. Paolo, Beatrice and all were very helpful. ..." - Jean
Save $1,211 Photo of Beautiful Tuscan Villa on a Large Estate
  • min $9,590/wk
  • max $15,680/wk
  • min $8,631/wk
  • Min Stay: 7 days
Sleeps 22 people
  • 11 double bedrooms
  • 11 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,211 when you book by Jun-30-2018**
" Wonderful...." - Naomi
  • min $1,890/wk
  • max $4,044/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" Great..." - Colleen And 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 $1,625/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 $1,890/wk
  • max $4,305/wk
  • Min Stay: 7 days
Sleeps 8 to 10 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" The property is beautiful! The view is amazing and you wake up every morning to a symphony of birds and frogs. The villa itself is rustic but nice and very comfo..." - Lisa
  • min $1,662/wk
  • max $3,561/wk
  • Min Stay: 3 days
Sleeps 10 to 12 people
  • 5 double bedrooms
  • 4 bathrooms
  • Swimming Pool
  • Washing Machine
" We were a group of 10 and really liked this villa. The property is spacious and the bedrooms are large. Loved the large fireplace in the living room...." - Pamela
  • min $673/wk
  • max $971/wk
  • Min Stay: 7 days
Sleeps 3 to 4 people
  • 1 single bedrooms
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" We had a amazing time in Tuscany and loved our little villa!..." - Melissa
  • min $6,930/wk
  • max $10,920/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" Wonderful...." - Dick
  • min $700/wk
  • max $1,540/wk
  • Min Stay: 3 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" The location was very good. Easy driving to some of the towns we wanted to visit, such as Pisa, Lucca and Siena. The beds were comfortable and the villa was roomy..." - Cheryl
  • min $709/wk
  • max $1,272/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $905/wk
  • max $1,465/wk
  • Min Stay: 3 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" We had a wonderful stay. The villa was just what we were looking for. The property manager was very good and gave us great information about what to see and wher..." - Virginia
  • min $1,182/wk
  • max $1,910/wk
  • Min Stay: 3 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" It is difficult to find the appropriate words to express how wonderful our experience at Casa della Fioraia was. The view we awoke to every day was spectacular. ..." - Bill
Save $413 Photo of Charming Tuscan Villa on Large Estate
  • min $3,290/wk
  • max $5,950/wk
  • min $2,961/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $413 when you book by Jun-30-2018**
 
Displaying 121 to 150 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..