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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 155 villas
Save $455 Photo of Villa Rental Chianti Tuscany Near Florence
  • min $2,300/wk
  • max $4,554/wk
  • min $2,070/wk
  • max $4,099/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 $455 when you book by Sep-30-2021**
" We had a wonderful time. The house was beautiful and everything we expected. ..." - Theresa
Save $839 Photo of Villa Rental in Tuscany, San Donato in Poggio
  • min $5,537/wk
  • max $8,391/wk
  • min $4,983/wk
  • max $7,552/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $839 when you book by Sep-30-2021**
" Wonderful..." - Aline
Save $347 Photo of Farmhouse Rental Near Certaldo, Tuscany
  • min $2,440/wk
  • max $3,467/wk
  • min $2,196/wk
  • max $3,120/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 $347 when you book by Sep-30-2021**
" Our overall experience staying at Donatella was simply fantastic. The villa is just beautiful. The accommodations were so nice and very comfortable. The views were..." - George
Save $2,695 Photo of Ancient Hamlet in Tuscany near Florence
  • min $21,952/wk
  • max $26,950/wk
  • min $19,757/wk
  • max $24,255/wk
  • Min Stay: 7 days
Sleeps 50 people
  • 25 double bedrooms
  • 25 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $2,695 when you book by Sep-30-2021**
" It was a wonderful experience from beginning to end. I can't express how much all my friends and family enjoyed their time at the property...." - Brendan
Save $166 Photo of Tuscan Apartment in Historic Castle
  • min $801/wk
  • max $1,659/wk
  • min $721/wk
  • max $1,493/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $166 when you book by Sep-30-2021**
Save $231 Photo of Tuscany Accommodation Within Walking Distance of Town
  • min $1,581/wk
  • max $2,305/wk
  • min $1,423/wk
  • max $2,075/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
** Save up to $231 when you book by Sep-30-2021**
" We had a great time at Poggio 2. Giulia was very helpful ..." - Karyn
Save $208 Photo of Tuscan Apartment in Historic Castle
  • min $1,125/wk
  • max $2,077/wk
  • min $1,013/wk
  • max $1,869/wk
  • Min Stay: 3 days
Sleeps 2 to 5 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $208 when you book by Sep-30-2021**
" Terrific!..." - Ross
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-30-2021**
" Our stay was the highlight of our trip to Italy. ..." - Patty
Save $398 Photo of Tuscan Villa with a Private Pool in a Village
  • min $966/wk
  • max $3,975/wk
  • min $869/wk
  • max $3,578/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $398 when you book by Sep-30-2021**
" Casa Donnini was absolutely wonderful. Great location. Pool. Store, bakery, butcher literally seconds away! A dream come true...." - Mark
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 Sep-30-2021**
" Lovely, relaxing stay with easy access to onsite property managers. ..." - Katie
  • min $1,961/wk
  • max $4,481/wk
  • Min Stay: 7 days
Sleeps 8 to 10 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Outstanding! The villa was even better than it looked in the pictures on the website. Check in was very easy and staff were very helpful in answering any questions..." - Julie
Save $822 Photo of Beautiful Large Villa Close to Florence
  • min $5,601/wk
  • max $8,215/wk
  • min $5,041/wk
  • max $7,393/wk
  • Min Stay: 5 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $822 when you book by Sep-30-2021**
" It was an amazing experience. The property was lovely and we used the pool daily...." - Linda
Save $905 Photo of Villa with Private Pool and Easy Train Access to Florence
  • min $2,124/wk
  • max $9,054/wk
  • min $1,912/wk
  • max $8,149/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 1 single bedrooms
  • 5 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $905 when you book by Sep-30-2021**
" We loved the villa! The size and location were perfect for us. We used the kitchen every day and the living room furniture was very comfortable. The pool table ..." - Patricia
Save $336 Photo of Apartment Rental in Chianti Tuscany
  • min $1,719/wk
  • max $3,361/wk
  • min $1,547/wk
  • max $3,025/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $336 when you book by Sep-30-2021**
" 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 $1,482 Photo of Villa Rental in Tuscany, Impruneta
  • min $10,381/wk
  • max $14,819/wk
  • min $9,343/wk
  • max $13,337/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,482 when you book by Sep-30-2021**
Save $351 Photo of Farmhouse Rental in Tuscany, Gambassi Terme
  • min $3,178/wk
  • max $3,506/wk
  • min $2,860/wk
  • max $3,155/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $351 when you book by Sep-30-2021**
Save $302 Photo of Ancient Hamlet in Tuscany near Florence
  • min $2,205/wk
  • max $3,019/wk
  • min $1,985/wk
  • max $2,717/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $302 when you book by Sep-30-2021**
" 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 $2,363 Photo of Grand Villa with Private Pool Overlooking Tuscan Vineyards
  • min $21,878/wk
  • max $23,628/wk
  • min $19,690/wk
  • max $21,265/wk
  • Min Stay: 3 days
Sleeps 22 people
  • 11 double bedrooms
  • 11 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $2,363 when you book by Sep-30-2021**
" Excellent. Best way to find the Villa was to use the Waze app. Simple...." - Alan
Save $2,975 Photo of One of Four Apartments on Large Tuscan Estate
  • min $1,681/wk
  • max $2,615/wk
  • min $1,513/wk
  • max $2,354/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $2,975 when you book by Sep-30-2021**
Save $1,050 Photo of Private Villa on a Castle Estate near Certaldo
  • min $9,102/wk
  • max $10,502/wk
  • min $8,192/wk
  • max $9,452/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,050 when you book by Sep-30-2021**
" The villa was in the most beautiful setting, the staff was absolutely fantastic and we enjoyed getting to know them and they took such good care of our large group..." - Vesna
Save $176 Photo of Tuscan Apartment in Historic Castle
  • min $985/wk
  • max $1,755/wk
  • min $887/wk
  • max $1,580/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $176 when you book by Sep-30-2021**
" 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 $282 Photo of Tuscan Apartment in Historic Castle
  • min $1,332/wk
  • max $2,824/wk
  • min $1,199/wk
  • max $2,542/wk
  • Min Stay: 3 days
Sleeps 8 people
  • 4 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $282 when you book by Sep-30-2021**
" We loved it. We were 6 woman so we bought local fare and cooked in our big kitchen. ..." - Alice Celine
Save $1,099 Photo of Family Friendly Villa Rental in Tuscany with Pool
  • min $3,381/wk
  • max $10,991/wk
  • min $3,043/wk
  • max $9,892/wk
  • Min Stay: 7 days
Sleeps 15 people
  • 1 single bedrooms
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,099 when you book by Sep-30-2021**
" Great week...." - Maria
Save $214 Photo of Tuscan Apartment in Historic Castle
  • min $978/wk
  • max $2,144/wk
  • min $880/wk
  • max $1,930/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $214 when you book by Sep-30-2021**
Save $149 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,127/wk
  • max $1,490/wk
  • min $1,014/wk
  • max $1,341/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $149 when you book by Sep-30-2021**
" 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 $133 Photo of Ancient Hamlet in Tuscany near Florence
  • min $971/wk
  • max $1,333/wk
  • min $874/wk
  • max $1,200/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $133 when you book by Sep-30-2021**
Save $262 Photo of One of Four Apartments on Large Tuscan Estate
  • min $1,681/wk
  • max $2,615/wk
  • min $1,513/wk
  • max $2,354/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $262 when you book by Sep-30-2021**
" Amazing place and a great location to explore the Tuscany region...." - Alex
Save $168 Photo of One of Four Apartments on Large Tuscan Estate
  • min $1,401/wk
  • max $1,681/wk
  • min $1,261/wk
  • max $1,513/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $168 when you book by Sep-30-2021**
" One of our favourite areas on our month-long trip in Italy. After staying in Florence this was such a pleasant, quiet week with gorgeous scenery, pool and friendl..." - Susan
Save $149 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,127/wk
  • max $1,490/wk
  • min $1,014/wk
  • max $1,341/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $149 when you book by Sep-30-2021**
Save $149 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,127/wk
  • max $1,490/wk
  • min $1,014/wk
  • max $1,341/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $149 when you book by Sep-30-2021**
 
Displaying 1 to 30 of 155 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..