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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 169 villas
Save $434 Photo of Villa Rental Chianti Tuscany Near Florence
  • min $2,300/wk
  • max $4,337/wk
  • min $2,070/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-10-2020**
" It was magical. When you arrive and open the gate, you are surrounded by roses, hydrangeas, geraniums (with colors I'd never seen) and olive trees. The Villa..." - Joan
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-10-2020**
" 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 Apr-10-2020**
" We loved our stay! The location is perfect and very peaceful. With a car everything is close and accessible. The villa was big for our family of 4 but we loved it...." - Pia
Save $938 Photo of Traditional Tuscan Villa on a Large Estate
  • min $3,738/wk
  • max $9,380/wk
  • min $3,364/wk
  • max $8,442/wk
  • Min Stay: 4 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $938 when you book by Apr-10-2020**
" Wonderful!..." - Chuck
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-10-2020**
" It was an experience of a lifetime - just awesome!..." - Carmita
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 7 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $206 when you book by Apr-10-2020**
" Perfect. ..." - Mario
Save $327 Photo of Farmhouse Rental Near Certaldo, Tuscany
  • min $2,440/wk
  • max $3,267/wk
  • min $2,196/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-10-2020**
" 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 $1,386 Photo of Beautiful Tuscan Villa on a Large Estate
  • min $5,880/wk
  • max $13,860/wk
  • min $5,292/wk
  • max $12,474/wk
  • Min Stay: 4 days
Sleeps 22 people
  • 11 double bedrooms
  • 11 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,386 when you book by Apr-10-2020**
" Wonderful...." - Naomi
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-10-2020**
" Enjoyed the villa and its location in the small town very much...." - Richard P
Save $2,788 Photo of Grand Villa with Private Pool Overlooking Tuscan Vineyards
  • min $21,878/wk
  • max $21,878/wk
  • min $19,090/wk
  • max $19,690/wk
  • Min Stay: 3 days
Sleeps 22 people
  • 11 double bedrooms
  • 11 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $2,788 when you book by Apr-10-2020**
" Excellent. Best way to find the Villa was to use the Waze app. Simple...." - Alan
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-10-2020**
" The view and being in a small town. ..." - Joseph
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 Apr-10-2020**
" 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 Apr-10-2020**
" Wonderful all around!..." - Cinnamon
Save $154 Photo of Holiday Accommodation in Chianti
  • min $841/wk
  • max $1,541/wk
  • min $757/wk
  • max $1,387/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $154 when you book by Apr-10-2020**
" Fantastic! Just as great as I thought it would be! The outdoor pool seating areas were amazing...." - Mary Ann
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-10-2020**
" 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 $170 Photo of Tuscan Apartment in Historic Castle
  • min $772/wk
  • max $1,699/wk
  • min $695/wk
  • max $1,529/wk
  • Min Stay: 3 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $170 when you book by Apr-10-2020**
" Wonderful. A magnificent castle with out-buildings in beautiful countryside. We rented 5 units - all in the out-buildings. I entered the same comments for all 5 ..." - Michael
Save $165 Photo of Tuscan Apartment in Historic Castle
  • min $978/wk
  • max $1,647/wk
  • min $880/wk
  • max $1,482/wk
  • Min Stay: 3 days
Sleeps 2 to 5 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $165 when you book by Apr-10-2020**
" Terrific!..." - Ross
Save $145 Photo of CastleApartment Rental in Tuscany, Montespertoli (Chianti Area)
  • min $944/wk
  • max $1,449/wk
  • min $850/wk
  • max $1,304/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $145 when you book by Apr-10-2020**
Save $2,310 Photo of Villa Rental in Tuscany, Castelfalfi
  • min $14,630/wk
  • max $23,100/wk
  • min $13,167/wk
  • max $20,790/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $2,310 when you book by Apr-10-2020**
Save $142 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,078/wk
  • max $1,421/wk
  • min $970/wk
  • max $1,279/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $142 when you book by Apr-10-2020**
Save $132 Photo of Tuscan Apartment in Historic Castle
  • min $696/wk
  • max $1,315/wk
  • min $626/wk
  • max $1,184/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $132 when you book by Apr-10-2020**
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-10-2020**
" Overall we had a good week. ..." - Phil
Save $330 Photo of Tuscan Villa with a Private Pool in a Village
  • min $693/wk
  • max $3,296/wk
  • min $624/wk
  • max $2,966/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $330 when you book by Apr-10-2020**
" Casa Donnini was absolutely wonderful. Great location. Pool. Store, bakery, butcher literally seconds away! A dream come true...." - Mark
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-10-2020**
" Beautiful villa...." - Mary Beth
Save $4,947 Photo of Castle Rental in Tuscany, Montespertoli (Chianti Area)
  • min $26,078/wk
  • max $49,471/wk
  • min $23,470/wk
  • max $44,524/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 $4,947 when you book by Apr-10-2020**
Save $196 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,470/wk
  • max $1,960/wk
  • min $1,323/wk
  • max $1,764/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $196 when you book by Apr-10-2020**
Save $142 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,078/wk
  • max $1,421/wk
  • min $970/wk
  • max $1,279/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $142 when you book by Apr-10-2020**
" 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 $155 Photo of Tuscan Apartment in Historic Castle
  • min $772/wk
  • max $1,545/wk
  • min $695/wk
  • max $1,391/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $155 when you book by Apr-10-2020**
" We liked the gardens and the castle next door, the views of the country, and the quietness. We slept well, but in the summer it's warm, and there is no A/C. A ..." - Carlos
Save $183 Photo of Tuscan Apartment in Historic Castle
  • min $927/wk
  • max $1,825/wk
  • min $834/wk
  • max $1,643/wk
  • Min Stay: 3 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $183 when you book by Apr-10-2020**
" 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
Save $2,042 Photo of Villa Rental in Tuscany, Strada in Chianti
  • min $11,669/wk
  • max $20,419/wk
  • min $10,502/wk
  • max $18,377/wk
  • Min Stay: 7 days
Sleeps 20 people
  • 10 double bedrooms
  • 11 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
** Save up to $2,042 when you book by Apr-10-2020**
 
Displaying 1 to 30 of 169 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..