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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 165 villas
Save $314 Photo of Chianti Farmhouse on a Wine Estate
  • min $1,662/wk
  • max $3,137/wk
  • min $1,496/wk
  • max $2,823/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $314 when you book by Apr-20-2021**
" Excellent. Beautiful house and property...." - Gary
Save $213 Photo of Apartment Rental in Tuscany, Gambassi Terme
  • min $1,281/wk
  • max $2,132/wk
  • min $1,153/wk
  • max $1,919/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $213 when you book by Apr-20-2021**
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 Apr-20-2021**
" Overall we had a good week. ..." - Phil
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 Apr-20-2021**
" 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 $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 Apr-20-2021**
" We loved it. We were 6 woman so we bought local fare and cooked in our big kitchen. ..." - Alice Celine
Save $221 Photo of Tuscany Accommodation Within Walking Distance of Town
  • min $1,512/wk
  • max $2,205/wk
  • min $1,361/wk
  • max $1,985/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
** Save up to $221 when you book by Apr-20-2021**
" We had a great time at Poggio 2. Giulia was very helpful ..." - Karyn
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 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $170 when you book by Apr-20-2021**
" 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 $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 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $170 when you book by Apr-20-2021**
" 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 $176 Photo of Tuscan Apartment in Historic Castle
  • min $700/wk
  • max $1,760/wk
  • min $630/wk
  • max $1,584/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $176 when you book by Apr-20-2021**
" We thoroughly enjoyed our stay and the property was very well-maintained. We would recommend staying here to others. We quickly realized, however, that some of the..." - Wendy
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 Apr-20-2021**
" 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 $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 Apr-20-2021**
Save $154 Photo of Holiday Accommodation in Chianti
  • min $841/wk
  • max $1,541/wk
  • min $757/wk
  • max $1,387/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $154 when you book by Apr-20-2021**
" The people managing the property are first class. Very conscientious and helpful. ..." - Bo
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 Apr-20-2021**
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
** Save up to $196 when you book by Apr-20-2021**
Save $127 Photo of Ancient Hamlet in Tuscany near Florence
  • min $931/wk
  • max $1,274/wk
  • min $838/wk
  • max $1,147/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $127 when you book by Apr-20-2021**
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 Apr-20-2021**
Save $185 Photo of Tuscan Apartment in Historic Castle
  • min $770/wk
  • max $1,853/wk
  • min $693/wk
  • max $1,668/wk
  • Min Stay: 3 days
Sleeps 5 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $185 when you book by Apr-20-2021**
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 Apr-20-2021**
" The setting is very quaint. ..." - Mike
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 Apr-20-2021**
Save $169 Photo of Apartment Rental in Tuscany, Gambassi Terme
  • min $953/wk
  • max $1,691/wk
  • min $858/wk
  • max $1,522/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Air Conditioning
** Save up to $169 when you book by Apr-20-2021**
Save $560 Photo of Tuscany Villa Rental near Greve
  • min $3,011/wk
  • max $5,601/wk
  • min $2,710/wk
  • max $5,041/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $560 when you book by Apr-20-2021**
" Our stay was the highlight of our trip to Italy. ..." - Patty
Save $154 Photo of Holiday Accommodation in Chianti
  • min $841/wk
  • max $1,541/wk
  • min $757/wk
  • max $1,387/wk
  • Min Stay: 7 days
Sleeps 5 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $154 when you book by Apr-20-2021**
" It was an amazing vacation with our family in this beautiful setting. Our host Leonardo was extremely gracious and very accommodating...." - Diana
Save $293 Photo of Tuscany Farmhouse Close to a Castle
  • min $1,235/wk
  • max $2,933/wk
  • min $1,112/wk
  • max $2,640/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $293 when you book by Apr-20-2021**
" This location is perfectly situated for all the day trips we had planned, from Cinque Terre to Siena. ..." - Sadia
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 Apr-20-2021**
" 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 $213 Photo of Apartment Rental in Tuscany, Gambassi Terme
  • min $1,281/wk
  • max $2,132/wk
  • min $1,153/wk
  • max $1,919/wk
  • Min Stay: 7 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $213 when you book by Apr-20-2021**
Save $213 Photo of Apartment Rental in Tuscany, Gambassi Terme
  • min $1,281/wk
  • max $2,132/wk
  • min $1,153/wk
  • max $1,919/wk
  • Min Stay: 7 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $213 when you book by Apr-20-2021**
Save $139 Photo of Tuscan Apartment in Historic Castle
  • min $700/wk
  • max $1,392/wk
  • min $630/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 Apr-20-2021**
" We had a delightful time at the castle. The apartment was lovely and well maintained. The castle was very scenic...." - Joan
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 Apr-20-2021**
" Absolutely wonderful vacation! ..." - Dean
Save $108 Photo of Tuscan Apartment in Historic Castle
  • min $490/wk
  • max $1,081/wk
  • min $441/wk
  • max $973/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $108 when you book by Apr-20-2021**
Save $124 Photo of Tuscan Apartment in Historic Castle
  • min $534/wk
  • max $1,235/wk
  • min $481/wk
  • max $1,112/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $124 when you book by Apr-20-2021**
 
Displaying 31 to 60 of 165 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..