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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 168 villas
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 Jan-31-2021**
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 Jan-31-2021**
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 6 people
  • 2 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $154 when you book by Jan-31-2021**
" Fantastic place with beautiful views, very secluded and quiet. Great and very large covered outdoor patio...." - Liz
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 Jan-31-2021**
" 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 $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 Jan-31-2021**
" This location is perfectly situated for all the day trips we had planned, from Cinque Terre to Siena. ..." - Sadia
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 Jan-31-2021**
" 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 $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 Jan-31-2021**
" Beautiful, large castle in a picture perfect location that seemed like something out of a Tuscan fantasy. ..." - Deborah
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 Jan-31-2021**
" Love this property. Second year in a row I have been there...." - Sadia
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 Jan-31-2021**
" 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 $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 Jan-31-2021**
" 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 Jan-31-2021**
" Ambiance. Staff was very good...." - Will
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 Jan-31-2021**
" Good...." - Randee
Save $971 Photo of Large Villa Rental in Tuscany Near Florence with Pool
  • min $6,721/wk
  • max $9,708/wk
  • min $6,049/wk
  • max $8,737/wk
  • Min Stay: 5 days
Sleeps 20 people
  • 2 single bedrooms
  • 9 double bedrooms
  • 11 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $971 when you book by Jan-31-2021**
" A wonderful two weeks was thoroughly enjoyed by our entire family of 20 people aged from 4 years up to 70 years. Facilities were excellent in every respect and ass..." - Terry
Save $155 Photo of Tuscan Apartment in Historic Castle
  • min $700/wk
  • max $1,545/wk
  • min $630/wk
  • max $1,391/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $155 when you book by Jan-31-2021**
" We liked the gardens and the castle next door, the views of the country, and the quietness. We slept well, but in the summer it's warm, and there is no A/C. A ..." - Carlos
Save $170 Photo of Tuscan Apartment in Historic Castle
  • min $770/wk
  • max $1,699/wk
  • min $693/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 Jan-31-2021**
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 Jan-31-2021**
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 Jan-31-2021**
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 Jan-31-2021**
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 Jan-31-2021**
" We had a delightful time at the castle. The apartment was lovely and well maintained. The castle was very scenic...." - Joan
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 Jan-31-2021**
Save $776 Photo of Beautiful Estate for Rent with Two Pools Near Certaldo
  • min $6,462/wk
  • max $7,755/wk
  • min $5,816/wk
  • max $6,980/wk
  • Min Stay: 4 days
Sleeps 12 to 14 people
  • 6 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $776 when you book by Jan-31-2021**
" It was awesome! And meeting Elizabeth and Adi, the owners, was a highlight! Loved them and hiking all over the property!..." - Anne
Save $458 Photo of Tuscany Farmhouse Near Florence
  • min $2,009/wk
  • max $4,575/wk
  • min $1,808/wk
  • max $4,118/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
** Save up to $458 when you book by Jan-31-2021**
" 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
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 Jan-31-2021**
" We had a great time at Poggio 2. Giulia was very helpful ..." - Karyn
Save $307 Photo of House Rental in Tuscany, Tavarnelle in val di Pesa
  • min $1,078/wk
  • max $3,065/wk
  • min $970/wk
  • max $2,759/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $307 when you book by Jan-31-2021**
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 Jan-31-2021**
Save $175 Photo of Tuscan Apartment in Historic Castle
  • min $709/wk
  • max $1,752/wk
  • min $638/wk
  • max $1,577/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $175 when you book by Jan-31-2021**
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 Jan-31-2021**
" Outstanding! The property and the villa were absolutely perfect and everything we hoped it would be!..." - Dana
Save $432 Photo of Tuscan Apartment in Historic Castle
  • min $1,960/wk
  • max $4,322/wk
  • min $1,764/wk
  • max $3,890/wk
  • Min Stay: 3 days
Sleeps 8 to 9 people
  • 4 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $432 when you book by Jan-31-2021**
" We had a very pleasant stay and would recommend the property...." - Amy
Save $968 Photo of Family Friendly Villa Rental in Tuscany with Pool
  • min $2,538/wk
  • max $9,677/wk
  • min $2,284/wk
  • max $8,709/wk
  • Min Stay: 7 days
Sleeps 15 people
  • 1 single bedrooms
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $968 when you book by Jan-31-2021**
" Great week...." - Maria
Save $1,120 Photo of Villas for Rent on Large Estate Near Certaldo
  • min $10,469/wk
  • max $11,202/wk
  • min $9,422/wk
  • max $10,082/wk
  • Min Stay: 4 days
Sleeps 24 to 28 people
  • 12 double bedrooms
  • 13 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,120 when you book by Jan-31-2021**
" Overall, it was positive...." - Cheryl
 
Displaying 61 to 90 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..