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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 187 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 Jun-20-2019**
" Couldn't have been any better. Loved every minute...." - Kathy
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 Jun-20-2019**
" We have been to Donatella twice because we love it there. It sits in the heart of Tuscany and the hosts are great...." - Katherine
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 Jun-20-2019**
" It was an amazing experience. The property was lovely and we used the pool daily...." - Linda
Save $356 Photo of Tuscany Villa Rental in Chianti
  • min $2,077/wk
  • max $3,558/wk
  • min $1,869/wk
  • max $3,202/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $356 when you book by Jun-20-2019**
" I loved our stay here! The property was beautiful and Elizabeth was a wonderful and attentive host...." - Alexis
  • 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 Jun-20-2019**
" 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 Jun-20-2019**
" Overall we had a good week. ..." - Phil
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 Jun-20-2019**
" 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 $167 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $1,226/wk
  • max $1,667/wk
  • min $1,103/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 $167 when you book by Jun-20-2019**
" It was a beautiful property and the staff was exceptional especially helping us through a difficult situation we encountered. We would return!..." - Kim
Save $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 Jun-20-2019**
" The property is very good and comfortable. Gina is the perfect host and the facilities are excellent...." - GARRY
Save $124 Photo of CastleApartment Rental in Tuscany, Montespertoli (Chianti Area)
  • min $559/wk
  • max $1,235/wk
  • min $503/wk
  • max $1,112/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $124 when you book by Jun-20-2019**
"The building itself, the surroundings, and Tuscany in general...." - Pawel
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 Jun-20-2019**
" 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 $637 Photo of Tuscany Villa on a Hill Close to Florence
  • min $4,411/wk
  • max $6,371/wk
  • min $3,970/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 $637 when you book by Jun-20-2019**
" Lovely, relaxing stay with easy access to onsite property managers. ..." - Katie
Save $1,693 Photo of Villa Rental in Tuscany, Tavarnelle in val di Pesa
  • min $9,299/wk
  • max $16,925/wk
  • min $8,369/wk
  • max $15,233/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Washing Machine
  • Air Conditioning
** Save up to $1,693 when you book by Jun-20-2019**
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 Jun-20-2019**
" Fantastic, better than our high expectations!..." - Harri
Save $304 Photo of Apartment Rental in Tuscany, Gambassi Terme
  • min $1,961/wk
  • max $3,039/wk
  • min $1,765/wk
  • max $2,735/wk
  • Min Stay: 7 days
Sleeps 6 to 8 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
** Save up to $304 when you book by Jun-20-2019**
Save $3,916 Photo of Castle Rental in Tuscany, Montespertoli (Chianti Area)
  • $39,157/wk
  • $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 Jun-20-2019**
Save $108 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $834/wk
  • max $1,079/wk
  • min $751/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 $108 when you book by Jun-20-2019**
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 Jun-20-2019**
" 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 $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 Jun-20-2019**
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 Jun-20-2019**
" Enjoyed the villa and its location in the small town very much...." - Richard P
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 Jun-20-2019**
" Loved it. It felt like a true escape to the countryside. ..." - Kathryn
Save $971 Photo of Large Villa Rental in Tuscany Near Florence with Pool
  • min $6,721/wk
  • max $9,708/wk
  • min $6,049/wk
  • max $8,737/wk
  • Min Stay: 5 days
Sleeps 20 people
  • 2 single bedrooms
  • 9 double bedrooms
  • 11 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $971 when you book by Jun-20-2019**
" 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
Save $324 Photo of Villa in Tuscany Near Certaldo and the Chianti Region
  • min $1,888/wk
  • max $3,235/wk
  • min $1,699/wk
  • max $2,912/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $324 when you book by Jun-20-2019**
" 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 $396 Photo of Family-Friendly Villa Rental in Tuscany with Pool
  • min $2,293/wk
  • max $3,963/wk
  • min $2,064/wk
  • max $3,567/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 $396 when you book by Jun-20-2019**
" Terrific. ..." - Claudia
Save $145 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,088/wk
  • max $1,451/wk
  • min $979/wk
  • max $1,306/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $145 when you book by Jun-20-2019**
Save $145 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,088/wk
  • max $1,451/wk
  • min $979/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 Jun-20-2019**
" 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 $289 Photo of Ancient Hamlet in Tuscany near Florence
  • min $2,107/wk
  • max $2,891/wk
  • min $1,896/wk
  • max $2,602/wk
  • Min Stay: 3 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $289 when you book by Jun-20-2019**
" 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
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 Jun-20-2019**
" It was excellent. The pool was great, very clean and Sonia was very helpful when we arrived. ..." - David
Save $378 Photo of Farmhouse Rental in Tuscany, Certaldo (Chianti Area)
  • min $777/wk
  • max $3,780/wk
  • min $699/wk
  • max $3,402/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $378 when you book by Jun-20-2019**
Save $293 Photo of Tuscany Farmhouse Close to a Castle
  • min $1,176/wk
  • max $2,933/wk
  • min $1,058/wk
  • max $2,640/wk
  • Min Stay: 3 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $293 when you book by Jun-20-2019**
" This location is perfectly situated for all the day trips we had planned, from Cinque Terre to Siena. ..." - Sadia
 
Displaying 1 to 30 of 187 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..