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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 170 villas
  • min $1,904/wk
  • max $2,891/wk
  • Min Stay: 3 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" 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
  • min $700/wk
  • max $1,263/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" We had a delightful time at the castle. The apartment was lovely and well maintained. The castle was very scenic...." - Joan
  • min $1,120/wk
  • max $2,660/wk
  • Min Stay: 3 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" This location is perfectly situated for all the day trips we had planned, from Cinque Terre to Siena. ..." - Sadia
  • min $6,721/wk
  • max $9,708/wk
  • Min Stay: 5 days
Sleeps 20 people
  • 2 single bedrooms
  • 9 double bedrooms
  • 11 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
" 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
  • min $4,411/wk
  • max $6,371/wk
  • Min Stay: 7 days
Sleeps 8 to 11 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" We loved everything about it. It was the perfect place to spend Christmas with our family. It was very roomy, and the separate apartment in the basement was nice t..." - Holly
  • min $1,319/wk
  • max $2,368/wk
  • Min Stay: 3 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" 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
  • min $986/wk
  • max $3,941/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Outstanding! The property and the villa were absolutely perfect and everything we hoped it would be!..." - Dana
  • min $1,372/wk
  • max $2,107/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Absolutely wonderful vacation! ..." - Dean
  • min $966/wk
  • max $2,107/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Luigi and his staff were great. Friendly and responsive...." - John
  • min $490/wk
  • max $980/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $771/wk
  • max $1,541/wk
  • Min Stay: 7 days
Sleeps 5 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" It was an amazing vacation with our family in this beautiful setting. Our host Leonardo was extremely gracious and very accommodating...." - Diana
  • min $966/wk
  • max $1,451/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" 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
  • min $1,471/wk
  • max $2,059/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Maid Service
" Amazing, would return tomorrow...." - Marcie
  • min $1,681/wk
  • max $1,961/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" Amazing place and a great location to explore the Tuscany region...." - Alex
  • min $1,961/wk
  • max $4,481/wk
  • Min Stay: 7 days
Sleeps 8 to 9 people
  • 4 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" The setting is very quaint. ..." - Mike
  • min $1,372/wk
  • max $1,960/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
  • min $532/wk
  • max $1,120/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Spacious apartment, clean and appropriately furnished. The bedroom is very good and comfortable, as is the bathroom...." - Real
  • min $1,015/wk
  • max $1,655/wk
  • Min Stay: 3 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $12,602/wk
  • max $14,702/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
  • min $1,372/wk
  • max $2,107/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
  • min $1,738/wk
  • max $4,451/wk
  • Min Stay: 7 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Fabulous...." - Jane
  • min $840/wk
  • max $1,655/wk
  • Min Stay: 3 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" 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
  • min $931/wk
  • max $1,494/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" 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
  • min $887/wk
  • max $1,494/wk
  • Min Stay: 3 days
Sleeps 2 to 5 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" 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
  • min $700/wk
  • max $1,540/wk
  • Min Stay: 3 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" 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
  • min $2,085/wk
  • max $4,676/wk
  • Min Stay: 7 days
Sleeps 5 to 8 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 4 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $1,108/wk
  • max $2,331/wk
  • Min Stay: 3 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Our family very much enjoyed the owners' warm hospitality. They were very accommodating. The view is wonderful and the location is peaceful. ..." - Taylor
  • min $1,316/wk
  • max $1,960/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
  • min $1,372/wk
  • max $2,107/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $812/wk
  • max $1,245/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
 
Displaying 61 to 90 of 170 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..