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Vacation Accommodation Chianti Tuscany Villa 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 >

Showing 1 to 30 of 151 properties
  • min $1,900/wk
  • max $3,590/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
" Our stay at the Villa was everything and more that we expected...." - John
  • min $1,830/wk
  • max $2,580/wk
  • min $1,647/wk
  • max $2,322/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $258 when you book by Feb-28-2010**
" Sublime! It was 2 weeks of sheer bliss. The villa and the location exceeded our expectations. Our best recommendation is that we didn't want to leave. ..." - Joanna
  • min $3,511/wk
  • max $6,671/wk
  • min $3,160/wk
  • max $6,004/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $667 when you book by Feb-28-2010**
" Our overall experience was excellent...except for the weather which was rainy five out of the nine days, but considering the time of year, what could one expect...." - Wade
  • min $1,920/wk
  • max $3,319/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Wonderful experience. Elizabeth was very gracious and accommodating and the villa was perfect. ..." - Amy
  • min $2,028/wk
  • max $3,477/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" There are very few moments in life that anyone can describe as magical but both of us use "magical experience" to describe Villa Certaldo. From the prope..." - Kathleen
  • min $5,319/wk
  • max $7,867/wk
  • Min Stay: 7 days
Sleeps 13 people
  • 1 single bedrooms
  • 6 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Our overall experience was excellent...." - Spencer
  • min $885/wk
  • max $1,845/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
" Loved villa life. Very relaxing. Property was well equipped...." - Linda
  • min $645/wk
  • max $1,334/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
" We loved the villa and would highly recommend it. We were greeted warmly and experienced no problems at all. ..." - LARRY
  • min $1,369/wk
  • max $1,737/wk
  • min $1,232/wk
  • max $1,563/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
** Save up to $174 when you book by Feb-28-2010**
" The accommodation was indeed a very romantic castle, and we had spectacular views. However, all this romantic medieval environment had some medieval inconvenience..." - Stephen
  • min $1,141/wk
  • max $1,930/wk
  • min $1,027/wk
  • max $1,737/wk
  • Min Stay: 7 days
Sleeps 5 to 6 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Maid Service
** Save up to $193 when you book by Feb-28-2010**
" The beautiful view of the countryside and the easy walk into town. We also loved the property manager, who was always so helpful and pleasant!..." - Lisa
  • min $834/wk
  • max $1,684/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
" It was a lovely experience. Loved the location, close to everything. Loved the views, loved the windows, interior simple but comfortable, other guests were inviti..." - Helen
  • min $645/wk
  • max $1,334/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
" The villa was clean. There was enough place for 4 people...." - Lise
  • min $785/wk
  • max $1,634/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
" Very satisfactory...." - Neil
  • min $1,141/wk
  • max $1,930/wk
  • min $1,027/wk
  • max $1,737/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 $193 when you book by Feb-28-2010**
" Excellent... we feel as though we had a real Tuscan experience...." - Dianne
  • min $1,285/wk
  • max $2,674/wk
  • Min Stay: 7 days
Sleeps 7 to 11 people
  • 1 single bedrooms
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Washing Machine
  • Maid Service
" This was a lovely, gracious villa, and I was thrilled when I first saw it. It was perfect for our group and far exceeded our expectations. Graziella, the woman i..." - Sarah
  • min $772/wk
  • max $1,080/wk
  • min $695/wk
  • max $972/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 $108 when you book by Feb-28-2010**
" Overall fantastic. We are planning to return next year and will definitely recommend to others. The the property caretaker was very pleasant to deal with and ext..." - Michael
  • min $1,369/wk
  • max $1,737/wk
  • min $1,232/wk
  • max $1,563/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
** Save up to $174 when you book by Feb-28-2010**
" Overwhelming, absolutely beautiful!..." - Tom
  • min $721/wk
  • max $1,307/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" Very good..." - Jan
  • min $1,208/wk
  • max $1,885/wk
  • Min Stay: 7 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
" The castle is a situated in a breathtakingly beautiful area.It was a charming 2 weeks. Friendly, helpful staff and a great pool...." - Camilla
  • min $1,193/wk
  • max $1,456/wk
  • min $1,074/wk
  • max $1,310/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
** Save up to $146 when you book by Feb-28-2010**
" We had a wonderful experience at Machiavelli 3. The location was central but the property was picturesque and pastoral. The staff was helpful and friendly. ..." - Martha
  • min $2,015/wk
  • max $4,204/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
" The area it was in was just what we wanted. The property was great. The town was within walking distant, and we could take a local bus anywhere we wanted to go. Th..." - Joseph
  • min $1,818/wk
  • max $2,766/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" This was a wonderful location. The villa was clean, had a great view, was well furnished and the manager was very accommodating. We had a wonderful stay, the pool ..." - Duane
  • min $2,307/wk
  • max $3,336/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" We had wonderful time at this location. I would say location, location, location...." - Randy
  • min $4,740/wk
  • max $5,925/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" It was a wonderful experience. We had rental cars and took a day trip each day all about 1 hour villa-to-location. Did not get lost due to GPS systems in the car..." - Phyllis
  • min $4,827/wk
  • max $6,734/wk
  • min $4,344/wk
  • max $6,061/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
** Save up to $673 when you book by Feb-28-2010**
" Everyone greatly enjoyed our time at the villa. The space was lovely and the amount of outside space was tremendous. Lots of areas for people to get 'lost' in an..." - Sandy
  • min $1,214/wk
  • max $2,067/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Maid Service
" Castello 14 e benissimo!..." - Sarah
  • min $1,264/wk
  • max $1,738/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Wonderful. We actually stayed in #4, rather than#6. The description of the property pales in comparison to reality. The views from the property are superb and ev..." - Joseph
  • min $4,385/wk
  • max $7,191/wk
  • min $3,947/wk
  • max $6,472/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $719 when you book by Feb-28-2010**
  • min $1,667/wk
  • max $2,194/wk
  • min $1,500/wk
  • max $1,975/wk
  • Min Stay: 7 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $219 when you book by Feb-28-2010**
" The villa met our needs perfectly. The grounds were gorgeous and peaceful, and the villa was impeccably restored. The girls in the office were very gracious and h..." - Erin
  • min $855/wk
  • max $1,756/wk
  • min $770/wk
  • max $1,580/wk
  • Min Stay: 7 days
Sleeps 5 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Maid Service
** Save up to $176 when you book by Feb-28-2010**
" Excellent. Rooms were new, well maintained and clean. Pool was great...." - Charles
 
Showing 1 to 30 of 151 properties

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..