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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 31 to 60 of 180 villas
Save $127 Photo of Tuscan Apartment in Historic Castle
  • min $647/wk
  • max $1,265/wk
  • min $582/wk
  • max $1,139/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $127 when you book by Sep-30-2018**
" The castle is beautiful...." - Serena
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 Sep-30-2018**
" We had a wonderful week at Certaldo 4. The villa was lovely, comfortable and immaculate. The grounds are beautifully landscaped and maintained. Sylvia, the prop..." - Janice
Save $634 Photo of Tuscany Accommodation Within Walking Distance of Town
  • min $4,032/wk
  • max $6,335/wk
  • min $3,629/wk
  • max $5,702/wk
  • Min Stay: 7 days
Sleeps 12 to 15 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $634 when you book by Sep-30-2018**
Save $174 Photo of Tuscan Apartment in Historic Castle
  • min $882/wk
  • max $1,738/wk
  • min $794/wk
  • max $1,564/wk
  • Min Stay: 3 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $174 when you book by Sep-30-2018**
" We absolutely loved our time at Il Castello 27! Our family loved the property and the people that worked there were so friendly and helpful!..." - Sharon
Save $119 Photo of Tuscan Apartment in Historic Castle
  • min $692/wk
  • max $1,192/wk
  • min $623/wk
  • max $1,073/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $119 when you book by Sep-30-2018**
" Ambiance. Staff was very good...." - Will
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 Sep-30-2018**
Save $2,021 Photo of Luxury Farmhouse in the Chianti Wine Region
  • min $13,108/wk
  • max $20,214/wk
  • min $11,797/wk
  • max $18,193/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 $2,021 when you book by Sep-30-2018**
" Wonderful...." - Jackie
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 Sep-30-2018**
" 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 $157 Photo of Tuscan Apartment in Historic Castle
  • min $887/wk
  • max $1,568/wk
  • min $798/wk
  • max $1,411/wk
  • Min Stay: 3 days
Sleeps 2 to 5 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $157 when you book by Sep-30-2018**
" Excellent. Relaxing. Different. One of the highlights was 25 school childen fom New Zealand staying overnight. Sharing a bus with them and then dinner later. They ..." - Edward
Save $445 Photo of Charming Apartments in Tuscany Perfect for a Family Holiday
  • min $2,085/wk
  • max $4,451/wk
  • min $1,877/wk
  • max $4,006/wk
  • Min Stay: 7 days
Sleeps 5 to 8 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 4 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $445 when you book by Sep-30-2018**
Save $445 Photo of Charming Apartment in Tuscany Perfect for a Family Holiday
  • min $1,738/wk
  • max $4,451/wk
  • min $1,564/wk
  • max $4,006/wk
  • Min Stay: 7 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $445 when you book by Sep-30-2018**
" Fabulous...." - Jane
Save $191 Photo of Tuscan Apartment in Historic Castle
  • min $840/wk
  • max $1,911/wk
  • min $756/wk
  • max $1,720/wk
  • Min Stay: 3 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $191 when you book by Sep-30-2018**
" It was comfortable, clean, and conveniently located. ..." - Misty
Save $206 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $1,471/wk
  • max $2,059/wk
  • min $1,324/wk
  • max $1,853/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Maid Service
** Save up to $206 when you book by Sep-30-2018**
" My wife and I had a wonderful stay at Machiavelli. The grounds and view of the countryside were exquisite. Our villa was a great mix of old world charm and modern ..." - Aaron
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 Sep-30-2018**
" Fabulous...." - Tom
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 5 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $154 when you book by Sep-30-2018**
" It was an amazing vacation with our family in this beautiful setting. Our host Leonardo was extremely gracious and very accommodating...." - Diana
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 Sep-30-2018**
" Fantastic place with beautiful views, very secluded and quiet. Great and very large covered outdoor patio...." - Liz
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 Sep-30-2018**
" The property was better than our lofty expectations. We were treated warmly and everything that was done for us and our family and guests exceeded our imagination..." - Ken
Save $249 Photo of Tuscan Apartment in Historic Castle
  • min $1,385/wk
  • max $2,487/wk
  • min $1,247/wk
  • max $2,238/wk
  • Min Stay: 3 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $249 when you book by Sep-30-2018**
" 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 $300 Photo of Tuscany Villa with Private Pool
  • min $1,587/wk
  • max $2,999/wk
  • min $1,428/wk
  • max $2,699/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $300 when you book by Sep-30-2018**
" It was wonderful and we would recommend it to anyone...." - Dolores
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 Sep-30-2018**
" The property was superb and we loved every minute of our stay there. ..." - Louise
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 Sep-30-2018**
" Our family very much enjoyed the owners' warm hospitality. They were very accommodating. The view is wonderful and the location is peaceful. ..." - Taylor
Save $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 Sep-30-2018**
" 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 $493 Photo of Tuscan Farmhouse Rental on Large Estate
  • min $3,571/wk
  • max $4,928/wk
  • min $3,214/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 Sep-30-2018**
Save $308 Photo of Tuscany Villa within Walking Distance to Greve
  • min $1,519/wk
  • max $3,079/wk
  • min $1,367/wk
  • max $2,771/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $308 when you book by Sep-30-2018**
" In very good condition. A real retreat with a fantastic view..." - Andrew
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 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $162 when you book by Sep-30-2018**
" Wonderful. A magnificent building in beautiful countryside. We rented 5 units - all in the out-buildings. I entered the same comments for all 5 units. ..." - Michael
Save $146 Photo of Charming 14th Century Apartment in the Center of a Medieval Town in Tuscany
  • $1,458/wk
  • $1,312/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 2 bathrooms
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $146 when you book by Sep-30-2018**
" The restoration is very good quality. Most of the furnishings are Ikea so they are functional and attractive. Antiques and paintings add to the atmosphere of the p..." - Allan
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 Sep-30-2018**
" This location is perfectly situated for all the day trips we had planned, from Cinque Terre to Siena. ..." - Sadia
Save $139 Photo of House Rental in Tuscany, Castelfiorentino
  • min $756/wk
  • max $1,386/wk
  • min $680/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 Sep-30-2018**
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
 
Displaying 31 to 60 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..