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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 165 villas
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 Apr-30-2021**
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 Apr-30-2021**
" We'll be back...." - Tammy
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 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $124 when you book by Apr-30-2021**
" Love this property. Second year in a row I have been there...." - Sadia
Save $133 Photo of Tuscan Apartment in Historic Castle
  • min $613/wk
  • max $1,328/wk
  • min $552/wk
  • max $1,195/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $133 when you book by Apr-30-2021**
" The castle is beautiful...." - Serena
Save $125 Photo of Tuscan Apartment in Historic Castle
  • min $692/wk
  • max $1,252/wk
  • min $623/wk
  • max $1,127/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $125 when you book by Apr-30-2021**
" Ambiance. Staff was very good...." - Will
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 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $154 when you book by Apr-30-2021**
" Fantastic! Just as great as I thought it would be! The outdoor pool seating areas were amazing...." - Mary Ann
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 Apr-30-2021**
" 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 $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 Apr-30-2021**
" It was comfortable, clean, and conveniently located. ..." - Misty
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 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $289 when you book by Apr-30-2021**
" Luigi and his staff were great. Friendly and responsive...." - John
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 Apr-30-2021**
" Very good. However, it was 104 most days and didn't cool off much at night. Good home base for day trips...." - Kelly
Save $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
** Save up to $213 when you book by Apr-30-2021**
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 Apr-30-2021**
" 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 $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 Apr-30-2021**
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
** Save up to $211 when you book by Apr-30-2021**
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 Apr-30-2021**
" 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 $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 Apr-30-2021**
" 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 $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 Apr-30-2021**
Save $149 Photo of CastleApartment Rental in Tuscany, Montagnana
  • min $871/wk
  • max $1,489/wk
  • min $784/wk
  • max $1,340/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $149 when you book by Apr-30-2021**
" Outstanding! The property and the villa were absolutely perfect and everything we hoped it would be!..." - Dana
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: 7 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 Apr-30-2021**
" 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 $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-30-2021**
Save $165 Photo of Tuscan Apartment in Historic Castle
  • min $709/wk
  • max $1,647/wk
  • min $638/wk
  • max $1,482/wk
  • Min Stay: 3 days
Sleeps 3 to 4 people
  • 1 single bedrooms
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $165 when you book by Apr-30-2021**
Save $233 Photo of Apartment Rental in Tuscany, Gambassi Terme
  • min $1,322/wk
  • max $2,327/wk
  • min $1,190/wk
  • max $2,094/wk
  • Min Stay: 7 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $233 when you book by Apr-30-2021**
Save $182 Photo of Apartment Rental in Tuscany, Tavarnelle in val di Pesa
  • min $1,092/wk
  • max $1,820/wk
  • min $983/wk
  • max $1,638/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $182 when you book by Apr-30-2021**
" 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 $570 Photo of Tuscany Accommodation Within Walking Distance of Town
  • min $4,032/wk
  • max $5,701/wk
  • min $3,629/wk
  • max $5,131/wk
  • Min Stay: 7 days
Sleeps 12 to 15 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $570 when you book by Apr-30-2021**
Save $1,482 Photo of Villa Rental in Tuscany, Impruneta
  • min $10,381/wk
  • max $14,819/wk
  • min $9,343/wk
  • max $13,337/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,482 when you book by Apr-30-2021**
Save $924 Photo of Tuscan Apartment in Historic Castle
  • min $1,015/wk
  • max $9,240/wk
  • min $914/wk
  • max $8,316/wk
  • Min Stay: 3 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $924 when you book by Apr-30-2021**
Save $170 Photo of Tuscan Apartment in Historic Castle
  • min $840/wk
  • max $1,699/wk
  • min $756/wk
  • max $1,529/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $170 when you book by Apr-30-2021**
" Beautiful, large castle in a picture perfect location that seemed like something out of a Tuscan fantasy. ..." - Deborah
Save $238 Photo of Tuscan Apartment in Historic Castle
  • min $1,147/wk
  • max $2,375/wk
  • min $1,032/wk
  • max $2,138/wk
  • Min Stay: 3 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $238 when you book by Apr-30-2021**
" Good...." - Randee
Save $493 Photo of Tuscan Farmhouse Rental on Large Estate
  • min $4,541/wk
  • max $4,928/wk
  • min $4,087/wk
  • max $4,435/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 up to $493 when you book by Apr-30-2021**
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 Apr-30-2021**
 
Displaying 61 to 90 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..