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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 168 villas
Save $980 Photo of Villa Rental in Tuscany, Gambassi Terme
  • min $6,791/wk
  • max $9,802/wk
  • min $6,112/wk
  • max $8,822/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $980 when you book by Jan-31-2021**
" Overall we had a good week. ..." - Phil
Save $139 Photo of Tuscan Apartment in Historic Castle
  • min $772/wk
  • max $1,392/wk
  • min $695/wk
  • max $1,253/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $139 when you book by Jan-31-2021**
" 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
Save $289 Photo of Ancient Hamlet in Tuscany near Florence
  • min $2,107/wk
  • max $2,891/wk
  • min $1,896/wk
  • max $2,602/wk
  • Min Stay: 7 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 Jan-31-2021**
" 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 $170 Photo of Tuscany Accommodation Within Walking Distance of Town
  • min $1,071/wk
  • max $1,701/wk
  • min $964/wk
  • max $1,531/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
** Save up to $170 when you book by Jan-31-2021**
Save $165 Photo of Tuscan Apartment in Historic Castle
  • min $928/wk
  • max $1,647/wk
  • min $835/wk
  • max $1,482/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $165 when you book by Jan-31-2021**
" 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 $448 Photo of Tuscan Villa with Gardens and Pool for a Family
  • min $1,961/wk
  • max $4,481/wk
  • min $1,765/wk
  • max $4,033/wk
  • Min Stay: 7 days
Sleeps 8 to 9 people
  • 4 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $448 when you book by Jan-31-2021**
" The setting is very quaint. ..." - Mike
Save $142 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,078/wk
  • max $1,421/wk
  • min $970/wk
  • max $1,279/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $142 when you book by Jan-31-2021**
Save $196 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,470/wk
  • max $1,960/wk
  • min $1,323/wk
  • max $1,764/wk
  • Min Stay: 7 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 Jan-31-2021**
Save $315 Photo of Tuscany Villa with Private Pool
  • min $1,634/wk
  • max $3,149/wk
  • min $1,471/wk
  • max $2,834/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $315 when you book by Jan-31-2021**
" The property was great but rather far from town...." - Betty
Save $154 Photo of Holiday Accommodation in Chianti
  • min $771/wk
  • max $1,541/wk
  • min $694/wk
  • max $1,387/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $154 when you book by Jan-31-2021**
" Fantastic! Just as great as I thought it would be! The outdoor pool seating areas were amazing...." - Mary Ann
Save $211 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,617/wk
  • max $2,107/wk
  • min $1,455/wk
  • max $1,896/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $211 when you book by Jan-31-2021**
Save $145 Photo of CastleApartment Rental in Tuscany, Montespertoli (Chianti Area)
  • min $858/wk
  • max $1,449/wk
  • min $772/wk
  • max $1,304/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $145 when you book by Jan-31-2021**
Save $201 Photo of Tuscan Apartment in Historic Castle
  • min $840/wk
  • max $2,007/wk
  • min $756/wk
  • max $1,806/wk
  • Min Stay: 3 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $201 when you book by Jan-31-2021**
" It was comfortable, clean, and conveniently located. ..." - Misty
Save $224 Photo of Tuscan Apartment in Historic Castle
  • min $1,050/wk
  • max $2,239/wk
  • min $945/wk
  • max $2,015/wk
  • Min Stay: 3 days
Sleeps 8 people
  • 4 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $224 when you book by Jan-31-2021**
" We loved it. We were 6 woman so we bought local fare and cooked in our big kitchen. ..." - Alice Celine
Save $162 Photo of Tuscan Apartment in Historic Castle
  • min $700/wk
  • max $1,624/wk
  • min $630/wk
  • max $1,462/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $162 when you book by Jan-31-2021**
" We'll be back...." - Tammy
Save $170 Photo of Tuscan Apartment in Historic Castle
  • min $700/wk
  • max $1,699/wk
  • min $630/wk
  • max $1,529/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 single bedrooms
  • 1 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $170 when you book by Jan-31-2021**
" 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 $188 Photo of Tuscan Apartment in Historic Castle
  • min $875/wk
  • max $1,879/wk
  • min $788/wk
  • max $1,691/wk
  • Min Stay: 3 days
Sleeps 4 to 6 people
  • 3 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $188 when you book by Jan-31-2021**
" Very good. However, it was 104 most days and didn't cool off much at night. Good home base for day trips...." - Kelly
Save $162 Photo of Tuscan Apartment in Historic Castle
  • min $700/wk
  • max $1,622/wk
  • min $630/wk
  • max $1,460/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $162 when you book by Jan-31-2021**
Save $132 Photo of Tuscan Apartment in Historic Castle
  • min $630/wk
  • max $1,315/wk
  • min $567/wk
  • max $1,184/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $132 when you book by Jan-31-2021**
Save $139 Photo of Tuscan Apartment in Historic Castle
  • min $622/wk
  • max $1,392/wk
  • min $560/wk
  • max $1,253/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $139 when you book by Jan-31-2021**
Save $1,115 Photo of Large Villa in the Chianti Hills Close to Florence
  • min $7,319/wk
  • max $11,152/wk
  • min $6,587/wk
  • max $10,037/wk
  • Min Stay: 4 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,115 when you book by Jan-31-2021**
" The property is in a fabulous location with incredible 360 views- including a view to Florence. The house is over 500 years old but has been modernized with 7 bed..." - Robert
Save $849 Photo of Villa with Private Pool and Easy Train Access to Florence
  • min $2,032/wk
  • max $8,490/wk
  • min $1,829/wk
  • max $7,641/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 1 single bedrooms
  • 5 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $849 when you book by Jan-31-2021**
" We loved the villa! The size and location were perfect for us. We used the kitchen every day and the living room furniture was very comfortable. The pool table ..." - Patricia
Save $448 Photo of Lovely Tuscan Villa with Swimming Pool and Views
  • min $1,961/wk
  • max $4,481/wk
  • min $1,765/wk
  • max $4,033/wk
  • Min Stay: 7 days
Sleeps 8 to 10 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $448 when you book by Jan-31-2021**
" 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
Save $261 Photo of Tuscan Apartment in Historic Castle
  • min $1,313/wk
  • max $2,611/wk
  • min $1,182/wk
  • max $2,350/wk
  • Min Stay: 3 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $261 when you book by Jan-31-2021**
" 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 $183 Photo of Tuscan Apartment in Historic Castle
  • min $840/wk
  • max $1,825/wk
  • min $756/wk
  • max $1,643/wk
  • Min Stay: 3 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $183 when you book by Jan-31-2021**
" 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
Save $1,271 Photo of Large Villa in Chianti Hills Close to Florence
  • min $8,215/wk
  • max $12,712/wk
  • min $7,393/wk
  • max $11,441/wk
  • Min Stay: 4 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 $1,271 when you book by Jan-31-2021**
" This was one of the best large group trips we have ever taken. The place was far better than we expected. Paolo, the owner/architect was a charming guy who was t..." - Richard
Save $211 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,617/wk
  • max $2,107/wk
  • min $1,455/wk
  • max $1,896/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $211 when you book by Jan-31-2021**
Save $211 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,617/wk
  • max $2,107/wk
  • min $1,455/wk
  • max $1,896/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $211 when you book by Jan-31-2021**
" Absolutely wonderful vacation! ..." - Dean
Save $183 Photo of Tuscan Apartment in Historic Castle
  • min $910/wk
  • max $1,825/wk
  • min $819/wk
  • max $1,643/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $183 when you book by Jan-31-2021**
Save $142 Photo of Tuscan Apartment in Historic Castle
  • min $709/wk
  • max $1,417/wk
  • min $638/wk
  • max $1,275/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $142 when you book by Jan-31-2021**
 
Displaying 31 to 60 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..