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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 179 villas
Save $245 Photo of Tuscany Accommodation Within Walking Distance of Town
  • min $1,512/wk
  • max $2,450/wk
  • min $1,361/wk
  • max $2,205/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
** Save up to $245 when you book by Dec-10-2018**
" 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 $289 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,904/wk
  • max $2,891/wk
  • min $1,714/wk
  • max $2,602/wk
  • Min Stay: 3 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $289 when you book by Dec-10-2018**
" 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
Save $1,764 Photo of Historic Tuscan Villa on a Wine Estate in the Chianti Region
  • min $9,382/wk
  • max $17,643/wk
  • min $8,444/wk
  • max $15,879/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
** Save up to $1,764 when you book by Dec-10-2018**
" Villa Carmina is wonderful. There were 13 adults in our party and the villa easily accommodated a group of that size. ..." - Bruce
Save $402 Photo of Farmhouse Rental in Tuscany, Castelfiorentino
  • min $2,521/wk
  • max $4,015/wk
  • min $2,269/wk
  • max $3,614/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $402 when you book by Dec-10-2018**
" Peaceful, serene, blissful retreat. Hidden among the hills near Castelfiorentino, the villa is a surprising find in the rural countryside. We loved the fact that ..." - Sandy
Save $423 Photo of Cozy Tuscan Farmhouse near Tavarnelle Val di Pesa
  • min $2,534/wk
  • max $4,228/wk
  • min $2,281/wk
  • max $3,805/wk
  • Min Stay: 7 days
Sleeps 12 to 15 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $423 when you book by Dec-10-2018**
Save $1,008 Photo of Tuscany Villa to Rent
  • min $7,000/wk
  • max $10,080/wk
  • min $6,300/wk
  • max $9,072/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,008 when you book by Dec-10-2018**
" Overall it was very good to excellent...." - Jill
Save $140 Photo of Apartment Rental in Tuscany, Tavarnelle in val di Pesa
  • min $840/wk
  • max $1,400/wk
  • min $756/wk
  • max $1,260/wk
  • Min Stay: 3 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $140 when you book by Dec-10-2018**
" 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
Save $213 Photo of Tuscan Apartment in Historic Castle
  • min $910/wk
  • max $2,133/wk
  • min $819/wk
  • max $1,920/wk
  • Min Stay: 3 days
Sleeps 8 people
  • 4 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $213 when you book by Dec-10-2018**
" We loved it. We were 6 woman so we bought local fare and cooked in our big kitchen. ..." - Alice Celine
Save $139 Photo of House Rental in Tuscany, Castelfiorentino
  • min $756/wk
  • max $1,386/wk
  • min $680/wk
  • max $1,247/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
  • Air Conditioning
** Save up to $139 when you book by Dec-10-2018**
Save $634 Photo of Tuscany Accommodation Within Walking Distance of Town
  • min $4,032/wk
  • max $6,335/wk
  • min $3,629/wk
  • max $5,702/wk
  • Min Stay: 7 days
Sleeps 12 to 15 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $634 when you book by Dec-10-2018**
Save $162 Photo of Tuscan Apartment in Historic Castle
  • min $700/wk
  • max $1,617/wk
  • min $630/wk
  • max $1,455/wk
  • Min Stay: 3 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $162 when you book by Dec-10-2018**
" 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
Save $125 Photo of Tuscan Apartment in Historic Castle
  • min $630/wk
  • max $1,252/wk
  • min $567/wk
  • max $1,127/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $125 when you book by Dec-10-2018**
Save $138 Photo of CastleApartment Rental in Tuscany, Montespertoli (Chianti Area)
  • min $856/wk
  • max $1,381/wk
  • min $770/wk
  • max $1,243/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $138 when you book by Dec-10-2018**
Save $196 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,316/wk
  • max $1,960/wk
  • min $1,184/wk
  • max $1,764/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $196 when you book by Dec-10-2018**
Save $1,092 Photo of Traditional Tuscan Villa on a Large Estate
  • min $6,930/wk
  • max $10,920/wk
  • min $6,237/wk
  • max $9,828/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,092 when you book by Dec-10-2018**
" Wonderful!..." - Chuck
Save $1,323 Photo of Large Villa in Chianti Hills Close to Florence
  • min $8,555/wk
  • max $13,228/wk
  • min $7,699/wk
  • max $11,905/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
** Save up to $1,323 when you book by Dec-10-2018**
" It was a wonderful place to stay. Paolo, Beatrice and all were very helpful. ..." - Jean
Save $162 Photo of Tuscan Apartment in Historic Castle
  • min $700/wk
  • max $1,617/wk
  • min $630/wk
  • max $1,455/wk
  • Min Stay: 3 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $162 when you book by Dec-10-2018**
" 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
Save $2,035 Photo of Grand Villa with Private Pool Overlooking Tuscan Vineyards
  • min $18,229/wk
  • max $20,351/wk
  • min $16,406/wk
  • max $18,316/wk
  • Min Stay: 7 days
Sleeps 22 people
  • 11 double bedrooms
  • 11 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $2,035 when you book by Dec-10-2018**
" Excellent. Best way to find the Villa was to use the Waze app. Simple...." - Alan
Save $292 Photo of House Rental in Tuscany, Tavarnelle in val di Pesa
  • min $1,042/wk
  • max $2,919/wk
  • min $938/wk
  • max $2,627/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $292 when you book by Dec-10-2018**
Save $196 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,316/wk
  • max $1,960/wk
  • min $1,184/wk
  • max $1,764/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $196 when you book by Dec-10-2018**
Save $1,949 Photo of Beautiful Large luxury Villa in Tuscany with Private Pool and Sauna
  • min $12,824/wk
  • max $19,488/wk
  • min $11,542/wk
  • max $17,539/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,949 when you book by Dec-10-2018**
" Superb villa. Probably Top Ten in Tuscany and Top Five for large groups...." - Samuel
Save $191 Photo of Tuscan Apartment in Historic Castle
  • min $840/wk
  • max $1,911/wk
  • min $756/wk
  • max $1,720/wk
  • Min Stay: 3 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $191 when you book by Dec-10-2018**
" It was comfortable, clean, and conveniently located. ..." - Misty
Save $118 Photo of Tuscan Apartment in Historic Castle
  • min $532/wk
  • max $1,176/wk
  • min $479/wk
  • max $1,058/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $118 when you book by Dec-10-2018**
" Love this property. Second year in a row I have been there...." - Sadia
Save $249 Photo of Tuscan Apartment in Historic Castle
  • min $1,385/wk
  • max $2,487/wk
  • min $1,247/wk
  • max $2,238/wk
  • Min Stay: 3 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $249 when you book by Dec-10-2018**
" Overall our stay at the villa was a wonderful experience and the views amazing. Just wish we could have stayed around long enough to enjoy more!..." - Anne
Save $157 Photo of Tuscan Apartment in Historic Castle
  • min $887/wk
  • max $1,568/wk
  • min $798/wk
  • max $1,411/wk
  • Min Stay: 3 days
Sleeps 2 to 5 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $157 when you book by Dec-10-2018**
" Excellent. Relaxing. Different. One of the highlights was 25 school childen fom New Zealand staying overnight. Sharing a bus with them and then dinner later. They ..." - Edward
Save $1,160 Photo of Large Villa in the Chianti Hills Close to Florence
  • min $7,616/wk
  • max $11,603/wk
  • min $6,854/wk
  • max $10,443/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,160 when you book by Dec-10-2018**
" Amazing. We has a wonderful time. ..." - Tim
Save $157 Photo of Tuscan Apartment in Historic Castle
  • min $931/wk
  • max $1,568/wk
  • min $838/wk
  • max $1,411/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $157 when you book by Dec-10-2018**
" 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
Save $162 Photo of Tuscan Apartment in Historic Castle
  • min $700/wk
  • max $1,617/wk
  • min $630/wk
  • max $1,455/wk
  • Min Stay: 3 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $162 when you book by Dec-10-2018**
" 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
Save $242 Photo of Apartment Rental in Tuscany, Gambassi Terme
  • min $923/wk
  • max $2,419/wk
  • min $831/wk
  • max $2,177/wk
  • Min Stay: 7 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $242 when you book by Dec-10-2018**
Save $118 Photo of Tuscan Apartment in Historic Castle
  • min $532/wk
  • max $1,176/wk
  • min $479/wk
  • max $1,058/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $118 when you book by Dec-10-2018**
 
Displaying 61 to 90 of 179 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..