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 31 to 60 of 179 villas
Save $279 Photo of Tuscany Farmhouse Close to a Castle
  • min $1,120/wk
  • max $2,793/wk
  • min $1,008/wk
  • max $2,514/wk
  • Min Stay: 3 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $279 when you book by Dec-20-2018**
" This location is perfectly situated for all the day trips we had planned, from Cinque Terre to Siena. ..." - Sadia
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 Dec-20-2018**
" 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 $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 Dec-20-2018**
" The setting is very quaint. ..." - Mike
Save $233 Photo of Apartment Rental in Tuscany, San Polo
  • min $1,108/wk
  • max $2,331/wk
  • min $997/wk
  • max $2,098/wk
  • Min Stay: 3 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $233 when you book by Dec-20-2018**
" Our family very much enjoyed the owners' warm hospitality. They were very accommodating. The view is wonderful and the location is peaceful. ..." - Taylor
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 Dec-20-2018**
" Fabulous...." - Tom
Save $477 Photo of Farmhouse Rental in Tuscany, Gambassi Terme
  • min $1,630/wk
  • max $4,766/wk
  • min $1,467/wk
  • max $4,289/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $477 when you book by Dec-20-2018**
Save $971 Photo of Beautiful Tuscany Villa for a Large Group with Spectacular Views
  • min $4,481/wk
  • max $9,708/wk
  • min $4,033/wk
  • max $8,737/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $971 when you book by Dec-20-2018**
" Our experience at Villa Pucci was absolute perfection! The house and view are spectacular. ..." - Amy
Save $404 Photo of Tuscany Villa within Walking Distance to Greve
  • min $1,890/wk
  • max $4,044/wk
  • min $1,701/wk
  • max $3,640/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $404 when you book by Dec-20-2018**
" We had a wonderful time. The house was in a perfect location. We walked 5 min to town. It was easy to take the bus to Florence. ..." - Trish
Save $245 Photo of Apartment Rental in Tuscany, San Polo
  • min $1,260/wk
  • max $2,450/wk
  • min $1,134/wk
  • max $2,205/wk
  • Min Stay: 3 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $245 when you book by Dec-20-2018**
Save $1,575 Photo of Private Villa on a Castle Estate near Certaldo
  • min $11,639/wk
  • max $15,752/wk
  • min $10,475/wk
  • max $14,177/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,575 when you book by Dec-20-2018**
" 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 $189 Photo of Tuscany Accommodation Within Walking Distance of Town
  • min $1,071/wk
  • max $1,890/wk
  • min $964/wk
  • max $1,701/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
** Save up to $189 when you book by Dec-20-2018**
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: 5 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 Dec-20-2018**
" It was awesome! And meeting Elizabeth and Adi, the owners, was a highlight! Loved them and hiking all over the property!..." - Anne
Save $133 Photo of Tuscan Apartment in Historic Castle
  • min $777/wk
  • max $1,326/wk
  • min $699/wk
  • max $1,193/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $133 when you book by Dec-20-2018**
" 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 $477 Photo of Farmhouse Rental in Tuscany, Gambassi Terme
  • min $1,630/wk
  • max $4,766/wk
  • min $1,467/wk
  • max $4,289/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $477 when you book by Dec-20-2018**
Save $1,370 Photo of Villas for Rent on Large Estate Near Certaldo
  • min $8,036/wk
  • max $13,700/wk
  • min $7,232/wk
  • max $12,330/wk
  • Min Stay: 5 days
Sleeps 24 to 28 people
  • 12 double bedrooms
  • 13 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,370 when you book by Dec-20-2018**
" Overall, it was positive...." - Cheryl
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 Dec-20-2018**
" Absolutely wonderful vacation! ..." - Dean
Save $211 Photo of Ancient Hamlet in Tuscany near Florence
  • min $966/wk
  • max $2,107/wk
  • min $869/wk
  • max $1,896/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $211 when you book by Dec-20-2018**
" Luigi and his staff were great. Friendly and responsive...." - John
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 Dec-20-2018**
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 Dec-20-2018**
" 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 $560 Photo of Tuscany Villa Rental near Greve
  • min $2,941/wk
  • max $5,601/wk
  • min $2,647/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 Dec-20-2018**
" Excellent. ..." - Thomas
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
** Save up to $211 when you book by Dec-20-2018**
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 Dec-20-2018**
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 Dec-20-2018**
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 Dec-20-2018**
Save $245 Photo of Tuscany Accommodation Within Walking Distance of Town
  • min $1,512/wk
  • max $2,450/wk
  • min $1,361/wk
  • max $2,205/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
** Save up to $245 when you book by Dec-20-2018**
" We loved everything about our stay. Three couples stayed in Poggio 2. We were very comfortable--the 3 bedroom, 3 bath apartment was perfect. It was quiet and p..." - Mary
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 Dec-20-2018**
" Villa Carmina is wonderful. There were 13 adults in our party and the villa easily accommodated a group of that size. ..." - Bruce
Save $431 Photo of Tuscany Farmhouse Near Florence
  • min $1,890/wk
  • max $4,305/wk
  • min $1,701/wk
  • max $3,875/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 $431 when you book by Dec-20-2018**
" 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 $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 Dec-20-2018**
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 Dec-20-2018**
" We loved it. We were 6 woman so we bought local fare and cooked in our big kitchen. ..." - Alice Celine
Save $196 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,372/wk
  • max $1,960/wk
  • min $1,235/wk
  • max $1,764/wk
  • Min Stay: 3 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 Dec-20-2018**
 
Displaying 31 to 60 of 179 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..