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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 91 to 120 of 165 villas
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 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
  • Air Conditioning
** Save up to $196 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 to 6 people
  • 2 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $154 when you book by Apr-20-2021**
" Fantastic place with beautiful views, very secluded and quiet. Great and very large covered outdoor patio...." - Liz
Save $444 Photo of Farmhouse Rental in Tuscany, Gambassi Terme
  • min $3,178/wk
  • max $4,438/wk
  • min $2,860/wk
  • max $3,994/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $444 when you book by Apr-20-2021**
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 Apr-20-2021**
Save $1,155 Photo of Chianti Classico Farmhouse with Stunning Views
  • min $4,323/wk
  • max $11,550/wk
  • min $3,891/wk
  • max $10,395/wk
  • Min Stay: 7 days
Sleeps 8 to 10 people
  • 2 single bedrooms
  • 4 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
** Save up to $1,155 when you book by Apr-20-2021**
" SPECTACULAR!..." - Linda
Save $1,033 Photo of Luxury Chianti Villa on a Wine Estate
  • $10,327/wk
  • $9,294/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,033 when you book by Apr-20-2021**
" Exceptional villa...." - Jerry
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 Apr-20-2021**
" 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 $1,330 Photo of Private Villa on a Castle Estate near Certaldo
  • min $9,102/wk
  • max $13,302/wk
  • min $8,192/wk
  • max $11,972/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,330 when you book by Apr-20-2021**
" The villa was in the most beautiful setting, the staff was absolutely fantastic and we enjoyed getting to know them and they took such good care of our large group..." - Vesna
Save $196 Photo of One of Four Apartments on Large Tuscan Estate
  • min $1,681/wk
  • max $1,961/wk
  • min $1,513/wk
  • max $1,765/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $196 when you book by Apr-20-2021**
" The property is very good and comfortable. Gina is the perfect host and the facilities are excellent...." - GARRY
Save $196 Photo of One of Four Apartments on Large Tuscan Estate
  • min $1,681/wk
  • max $1,961/wk
  • min $1,513/wk
  • max $1,765/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $196 when you book by Apr-20-2021**
Save $196 Photo of One of Four Apartments on Large Tuscan Estate
  • min $1,681/wk
  • max $1,961/wk
  • min $1,513/wk
  • max $1,765/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $196 when you book by Apr-20-2021**
" Amazing place and a great location to explore the Tuscany region...." - Alex
Save $163 Photo of One of Four Apartments on Large Tuscan Estate
  • min $1,401/wk
  • max $1,625/wk
  • min $1,261/wk
  • max $1,463/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $163 when you book by Apr-20-2021**
" One of our favourite areas on our month-long trip in Italy. After staying in Florence this was such a pleasant, quiet week with gorgeous scenery, pool and friendl..." - Susan
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 Apr-20-2021**
" The property was great but rather far from town...." - Betty
Save $458 Photo of Farmhouse Rental in Tuscany, Gambassi Terme
  • min $2,460/wk
  • max $4,582/wk
  • min $2,214/wk
  • max $4,124/wk
  • Min Stay: 5 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $458 when you book by Apr-20-2021**
Save $658 Photo of Villa Rental in Tuscany, Rufina
  • min $5,040/wk
  • max $6,580/wk
  • min $4,536/wk
  • max $5,922/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
** Save up to $658 when you book by Apr-20-2021**
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 Apr-20-2021**
" Great week...." - Maria
Save $139 Photo of House Rental in Tuscany, Castelfiorentino
  • min $798/wk
  • max $1,386/wk
  • min $718/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 Apr-20-2021**
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 Apr-20-2021**
" 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 $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 Apr-20-2021**
" Superb villa. Probably Top Ten in Tuscany and Top Five for large groups...." - Samuel
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 Apr-20-2021**
" 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 $1,100 Photo of Villa Rental in Tuscany, Impruneta
  • min $6,797/wk
  • max $10,997/wk
  • min $6,117/wk
  • max $9,897/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,100 when you book by Apr-20-2021**
Save $657 Photo of Large Farmhouse for Group near Florence
  • min $2,999/wk
  • max $6,569/wk
  • min $2,699/wk
  • max $5,912/wk
  • Min Stay: 7 days
Sleeps 16 to 18 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $657 when you book by Apr-20-2021**
" Fabulous...." - Austin
Save $1,080 Photo of Villa Rental in Tuscany, Montespertoli (Chianti Area)
  • min $7,000/wk
  • max $10,801/wk
  • min $6,300/wk
  • max $9,721/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,080 when you book by Apr-20-2021**
Save $2,188 Photo of Grand Villa with Private Pool Overlooking Tuscan Vineyards
  • $21,878/wk
  • $19,690/wk
  • Min Stay: 3 days
Sleeps 22 people
  • 11 double bedrooms
  • 11 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $2,188 when you book by Apr-20-2021**
" Excellent. Best way to find the Villa was to use the Waze app. Simple...." - Alan
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 Apr-20-2021**
" It was awesome! And meeting Elizabeth and Adi, the owners, was a highlight! Loved them and hiking all over the property!..." - Anne
Save $1,378 Photo of Beautiful Tuscan Villa with Tower and Private Swimming Pool near Florence
  • min $8,860/wk
  • max $13,782/wk
  • min $7,974/wk
  • max $12,404/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,378 when you book by Apr-20-2021**
" Beautiful villa...." - Mary Beth
Save $155 Photo of Walk To Small Town for Cappuccino in Tuscany
  • min $953/wk
  • max $1,550/wk
  • min $858/wk
  • max $1,395/wk
  • Min Stay: 7 days
Sleeps 5 to 6 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $155 when you book by Apr-20-2021**
" It was an experience of a lifetime - just awesome!..." - Carmita
Save $495 Photo of Family-Friendly Tuscan Villa with Private Pool
  • min $1,961/wk
  • max $4,947/wk
  • min $1,765/wk
  • max $4,452/wk
  • Min Stay: 7 days
Sleeps 10 to 12 people
  • 5 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $495 when you book by Apr-20-2021**
" Fabulous...." - Tom
Save $1,568 Photo of Beautiful Tuscan Villa on a Large Estate
  • min $9,100/wk
  • max $15,680/wk
  • min $8,190/wk
  • max $14,112/wk
  • Min Stay: 7 days
Sleeps 29 people
  • 5 single bedrooms
  • 12 double bedrooms
  • 16 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
** Save up to $1,568 when you book by Apr-20-2021**
 
Displaying 91 to 120 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..