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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 >

Displaying 1 to 30 of 186 villas
Save $434 Photo of Villa Rental Chianti Tuscany Near Florence
  • min $2,190/wk
  • max $4,337/wk
  • min $1,971/wk
  • max $3,903/wk
  • Min Stay: 3 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $434 when you book by Apr-30-2019**
" Couldn't have been any better. Loved every minute...." - Kathy
Save $784 Photo of Beautiful Large Villa Close to Florence
  • min $5,601/wk
  • max $7,841/wk
  • min $5,041/wk
  • max $7,057/wk
  • Min Stay: 5 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $784 when you book by Apr-30-2019**
" It was an amazing experience. The property was lovely and we used the pool daily...." - Linda
Save $1,245 Photo of Tuscany Villa Rental in Chianti
  • min $2,077/wk
  • max $3,558/wk
  • min $1,350/wk
  • max $2,313/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,245 when you book by Apr-30-2019**
" I loved our stay here! The property was beautiful and Elizabeth was a wonderful and attentive host...." - Alexis
Save $327 Photo of Farmhouse Rental Near Certaldo, Tuscany
  • min $2,075/wk
  • max $3,267/wk
  • min $1,868/wk
  • max $2,940/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $327 when you book by Apr-30-2019**
" The overall experience can be best described in one word- magnifica! We would highly recommend this villa because it had everything we could possible need. It is d..." - Paula
  • 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 Apr-30-2019**
" We had a amazing time in Tuscany and loved our little villa!..." - Melissa
Save $980 Photo of Villa Rental in Tuscany, Gambassi Terme
  • min $6,791/wk
  • max $9,802/wk
  • min $6,112/wk
  • max $8,822/wk
  • Min Stay: 3 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $980 when you book by Apr-30-2019**
" Overall we had a good week. ..." - Phil
Save $317 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $1,226/wk
  • max $1,667/wk
  • min $993/wk
  • max $1,500/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
** Save up to $317 when you book by Apr-30-2019**
" It was a beautiful property and the staff was exceptional especially helping us through a difficult situation we encountered. We would return!..." - Kim
Save $1,284 Photo of Villa in Tuscany Near Certaldo and the Chianti Region
  • min $1,780/wk
  • max $3,235/wk
  • min $1,073/wk
  • max $2,209/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,284 when you book by Apr-30-2019**
" Fantastic, better than our high expectations!..." - Harri
Save $391 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $1,471/wk
  • max $2,059/wk
  • min $1,192/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 $391 when you book by Apr-30-2019**
" 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 $118 Photo of CastleApartment Rental in Tuscany, Montespertoli (Chianti Area)
  • min $559/wk
  • max $1,176/wk
  • min $503/wk
  • max $1,058/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $118 when you book by Apr-30-2019**
"The building itself, the surroundings, and Tuscany in general...." - Pawel
Save $155 Photo of Charming Apartment in Chianti Overlooking the Countryside
  • min $953/wk
  • max $1,550/wk
  • min $858/wk
  • max $1,395/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 $155 when you book by Apr-30-2019**
" The view and being in a small town. ..." - Joseph
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 Apr-30-2019**
" The property is very good and comfortable. Gina is the perfect host and the facilities are excellent...." - GARRY
Save $391 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $1,471/wk
  • max $2,059/wk
  • min $1,192/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 $391 when you book by Apr-30-2019**
" This was the most wonderful experience I have ever had. Think of the movie Under the Tuscan Sun... well, this villa is exactly that on steroids! So romantic, staf..." - Jackie
Save $1,378 Photo of Beautiful Tuscan Villa with Tower and Private Swimming Pool near Florence
  • min $8,860/wk
  • max $13,782/wk
  • min $7,974/wk
  • max $12,404/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,378 when you book by Apr-30-2019**
Save $120 Photo of Cozy Apartment Rental in the Chianti Area
  • min $766/wk
  • max $1,195/wk
  • min $689/wk
  • max $1,076/wk
  • Min Stay: 7 days
Sleeps 5 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $120 when you book by Apr-30-2019**
" Enjoyed the villa and its location in the small town very much...." - Richard P
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 Apr-30-2019**
" 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 $3,916 Photo of Castle Rental in Tuscany, Montespertoli (Chianti Area)
  • min $35,670/wk
  • max $39,157/wk
  • min $32,103/wk
  • max $35,241/wk
  • Min Stay: 7 days
Sleeps 80 to 120 people
  • 1 single bedrooms
  • 42 double bedrooms
  • 35 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $3,916 when you book by Apr-30-2019**
Save $205 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $834/wk
  • max $1,079/wk
  • min $676/wk
  • max $971/wk
  • Min Stay: 7 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
** Save up to $205 when you book by Apr-30-2019**
Save $700 Photo of Tuscany Vacation Rental
  • min $4,200/wk
  • max $7,000/wk
  • min $3,780/wk
  • max $6,300/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $700 when you book by Apr-30-2019**
Save $155 Photo of Walk To Small Town for Cappuccino in Tuscany
  • min $953/wk
  • max $1,550/wk
  • min $858/wk
  • max $1,395/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 $155 when you book by Apr-30-2019**
" It was excellent. The pool was great, very clean and Sonia was very helpful when we arrived. ..." - David
Save $1,210 Photo of Tuscany Villa on a Hill Close to Florence
  • min $4,411/wk
  • max $6,371/wk
  • min $3,573/wk
  • max $5,734/wk
  • Min Stay: 7 days
Sleeps 8 to 11 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,210 when you book by Apr-30-2019**
" Lovely, relaxing stay with easy access to onsite property managers. ..." - Katie
Save $254 Photo of Chianti Farmhouse on a Wine Estate
  • min $1,289/wk
  • max $2,539/wk
  • min $1,160/wk
  • max $2,285/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $254 when you book by Apr-30-2019**
" It is a beautiful setting for a relaxed vacation...." - ANNAMMA
Save $1,132 Photo of Villa in Tuscany Near Certaldo and the Chianti Region
  • min $1,888/wk
  • max $3,235/wk
  • min $1,227/wk
  • max $2,103/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,132 when you book by Apr-30-2019**
" Our experience was very soul-refreshing with the family at La Solaia. We enjoyed the location and the home. The kitchen was stocked with enough basic equipment to ..." - Dana
Save $1,387 Photo of Family-Friendly Villa Rental in Tuscany with Pool
  • min $2,293/wk
  • max $3,963/wk
  • min $1,490/wk
  • max $2,576/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,387 when you book by Apr-30-2019**
" Terrific. ..." - Claudia
Save $2,021 Photo of Luxury Farmhouse in the Chianti Wine Region
  • min $13,109/wk
  • max $20,214/wk
  • min $11,798/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 Apr-30-2019**
" Wonderful...." - Jackie
Save $1,470 Photo of Rural Woodland Tuscan villa with Pool and BBQ near Montaione
  • min $8,402/wk
  • max $14,702/wk
  • min $7,562/wk
  • max $13,232/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,470 when you book by Apr-30-2019**
Save $1,733 Photo of Luxury Chianti Villa Near a Small Town
  • min $11,375/wk
  • max $17,325/wk
  • min $10,238/wk
  • max $15,593/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,733 when you book by Apr-30-2019**
" What a lovely villa! The location was perfect to get away from the crowds of Florence. Such a beautiful setting amongst the olive trees and vineyards nearby...." - Cyndi
Save $279 Photo of Tuscany Farmhouse Close to a Castle
  • min $1,176/wk
  • max $2,793/wk
  • min $1,058/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 Apr-30-2019**
" This location is perfectly situated for all the day trips we had planned, from Cinque Terre to Siena. ..." - Sadia
Save $282 Photo of Apartment Rental in Chianti Tuscany
  • min $1,718/wk
  • max $2,820/wk
  • min $1,546/wk
  • max $2,538/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $282 when you book by Apr-30-2019**
" We had a very nice stay, and we would stay there again. It was convenient to Florence and other cities. We spent our days away from the villa, so our time there ..." - Mather
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 5 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $157 when you book by Apr-30-2019**
" 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
 
Displaying 1 to 30 of 186 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..