Suitcase

Your Suitcase contains your favorite villas and details of your upcoming trip. Sign up to use this feature.
Rated Excellent By Trip Advisor

Quick Filter

Travelers
Arrival Date
Departure Date
Max Price per Week

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 180 villas
Save $875 Photo of Tuscany Villa to Rent
  • min $7,000/wk
  • max $8,750/wk
  • min $6,300/wk
  • max $7,875/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $875 when you book by Sep-30-2018**
" Overall it was very good to excellent...." - Jill
Save $168 Photo of Tuscan Apartment in Historic Castle
  • min $735/wk
  • max $1,676/wk
  • min $662/wk
  • max $1,508/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $168 when you book by Sep-30-2018**
" 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 $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: 3 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 Sep-30-2018**
" 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 $229 Photo of Apartment Rental in Tuscany, San Polo
  • min $1,185/wk
  • max $2,294/wk
  • min $1,067/wk
  • max $2,065/wk
  • Min Stay: 3 days
Sleeps 8 people
  • 4 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $229 when you book by Sep-30-2018**
Save $200 Photo of Tuscany Apartment Near Florence with Restaurant
  • min $1,050/wk
  • max $2,000/wk
  • min $945/wk
  • max $1,800/wk
  • Min Stay: 3 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $200 when you book by Sep-30-2018**
" My family loved staying at the villa. The setting was beautiful. The owners were very welcoming, helpful, and great cooks! They prepare meals on Friday, Saturday..." - Lisa
Save $179 Photo of Tuscan Apartment in Historic Castle
  • min $916/wk
  • max $1,790/wk
  • min $824/wk
  • max $1,611/wk
  • Min Stay: 3 days
Sleeps 4 to 6 people
  • 3 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $179 when you book by Sep-30-2018**
" Very good. However, it was 104 most days and didn't cool off much at night. Good home base for day trips...." - Kelly
Save $133 Photo of Tuscan Apartment in Historic Castle
  • min $653/wk
  • max $1,326/wk
  • min $588/wk
  • max $1,193/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 Sep-30-2018**
Save $135 Photo of Tuscan Apartment in Historic Castle
  • min $793/wk
  • max $1,350/wk
  • min $714/wk
  • max $1,215/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $135 when you book by Sep-30-2018**
Save $121 Photo of Tuscany Apartment with Views Over the Chianti Classico Hills
  • min $628/wk
  • max $1,212/wk
  • min $565/wk
  • max $1,091/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $121 when you book by Sep-30-2018**
Save $157 Photo of Tuscan Apartment in Historic Castle
  • min $931/wk
  • max $1,568/wk
  • min $838/wk
  • max $1,411/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $157 when you book by Sep-30-2018**
" 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 $174 Photo of Tuscan Apartment in Historic Castle
  • min $1,015/wk
  • max $1,738/wk
  • min $914/wk
  • max $1,564/wk
  • Min Stay: 3 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $174 when you book by Sep-30-2018**
Save $211 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,372/wk
  • max $2,107/wk
  • min $1,235/wk
  • max $1,896/wk
  • Min Stay: 3 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 Sep-30-2018**
" Absolutely wonderful vacation! ..." - Dean
Save $752 Photo of Beautiful Estate for Rent with Two Pools Near Certaldo
  • min $3,613/wk
  • max $7,521/wk
  • min $3,252/wk
  • max $6,769/wk
  • Min Stay: 7 days
Sleeps 12 to 14 people
  • 6 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $752 when you book by Sep-30-2018**
" It was awesome! And meeting Elizabeth and Adi, the owners, was a highlight! Loved them and hiking all over the property!..." - Anne
Save $1,764 Photo of Historic Tuscan Villa on a Wine Estate in the Chianti Region
  • min $9,382/wk
  • max $17,643/wk
  • min $8,444/wk
  • max $15,879/wk
  • Min Stay: 7 days
Sleeps 13 to 14 people
  • 1 single bedrooms
  • 6 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,764 when you book by Sep-30-2018**
" Villa Carmina is wonderful. There were 13 adults in our party and the villa easily accommodated a group of that size. ..." - Bruce
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 Sep-30-2018**
Save $356 Photo of Apartment Rental in Tuscany, San Polo
  • min $1,662/wk
  • max $3,561/wk
  • min $1,496/wk
  • max $3,205/wk
  • Min Stay: 3 days
Sleeps 10 to 12 people
  • 5 double bedrooms
  • 4 bathrooms
  • Swimming Pool
  • Washing Machine
** Save up to $356 when you book by Sep-30-2018**
" We were a group of 10 and really liked this villa. The property is spacious and the bedrooms are large. Loved the large fireplace in the living room...." - Pamela
Save $226 Photo of Tuscan Apartment in Historic Castle
  • min $1,148/wk
  • max $2,261/wk
  • min $1,033/wk
  • max $2,035/wk
  • Min Stay: 3 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $226 when you book by Sep-30-2018**
" Good...." - Randee
Save $145 Photo of Ancient Hamlet in Tuscany near Florence
  • min $966/wk
  • max $1,451/wk
  • min $869/wk
  • max $1,306/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $145 when you book by Sep-30-2018**
" It was the most wonderful place. So very near Firenze and yet in the quiet and lovely countryside. The administrator was very helpful and charming. We enjoy every ..." - Susana
Save $1,106 Photo of Chianti Classico Farmhouse with Stunning Views
  • min $4,138/wk
  • max $11,055/wk
  • min $3,724/wk
  • max $9,950/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 $1,106 when you book by Sep-30-2018**
" Once in a lifetime experience...." - Tom
Save $103 Photo of Tuscan Apartment in Historic Castle
  • min $516/wk
  • max $1,029/wk
  • min $464/wk
  • max $926/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $103 when you book by Sep-30-2018**
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 Sep-30-2018**
" Very comfortable, beautiful home. Great owners who were very helpful to us. ..." - Bruna
Save $213 Photo of Tuscan Apartment in Historic Castle
  • min $910/wk
  • max $2,133/wk
  • min $819/wk
  • max $1,920/wk
  • Min Stay: 3 days
Sleeps 8 people
  • 4 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $213 when you book by Sep-30-2018**
" We loved it. We were 6 woman so we bought local fare and cooked in our big kitchen. ..." - Alice Celine
  • min $673/wk
  • max $971/wk
  • min $606/wk
  • max $874/wk
  • Min Stay: 7 days
Sleeps 3 to 4 people
  • 1 single bedrooms
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $97 when you book by Sep-30-2018**
" We had a amazing time in Tuscany and loved our little villa!..." - Melissa
Save $289 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,904/wk
  • max $2,891/wk
  • min $1,714/wk
  • max $2,602/wk
  • Min Stay: 3 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 Sep-30-2018**
" 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 $125 Photo of Ancient Hamlet in Tuscany near Florence
  • min $812/wk
  • max $1,245/wk
  • min $731/wk
  • max $1,121/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $125 when you book by Sep-30-2018**
Save $147 Photo of Tuscan Apartment in Historic Castle
  • min $700/wk
  • max $1,470/wk
  • min $630/wk
  • max $1,323/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $147 when you book by Sep-30-2018**
" 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 $199 Photo of Tuscany Apartment with Views Over the Chianti Classico Hills
  • min $945/wk
  • max $1,986/wk
  • min $851/wk
  • max $1,787/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $199 when you book by Sep-30-2018**
" Comfortable...." - Jess
Save $162 Photo of Tuscan Apartment in Historic Castle
  • min $700/wk
  • max $1,617/wk
  • min $630/wk
  • max $1,455/wk
  • Min Stay: 3 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $162 when you book by Sep-30-2018**
" 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 $162 Photo of Tuscan Apartment in Historic Castle
  • min $882/wk
  • max $1,617/wk
  • min $794/wk
  • max $1,455/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $162 when you book by Sep-30-2018**
" Beautiful, large castle in a picture perfect location that seemed like something out of a Tuscan fantasy. ..." - Deborah
Save $164 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,088/wk
  • max $1,638/wk
  • min $979/wk
  • max $1,474/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $164 when you book by Sep-30-2018**
 
Displaying 61 to 90 of 180 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. With so much to do in the area, everyone in your group will love the area. View our Rental Villas in South Florence..