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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 132 villas
Save $507 Photo of Farmhouse Rental Near Certaldo, Tuscany
  • min $3,764/wk
  • max $5,070/wk
  • min $3,388/wk
  • max $4,563/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 $507 when you book by Jun-10-2023**
" We enjoyed it very much. We have been to Tuscany several times and we were very pleased with everything at Donatella. When we arrived there was a welcome basket of..." - Bonnie
  • Enquire for Rates
Sleeps 8 to 11 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Driving through the gates and to the property is absolutely lovely. The villa was extremely relaxing with a wonderful view and in a great location...." - Melissa
  • Enquire for Rates
Sleeps 20 people
  • 10 double bedrooms
  • 11 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
Save $1,400 Photo of Beautiful Tuscany Villa for a Large Group with Spectacular Views
  • min $7,001/wk
  • max $14,002/wk
  • min $6,301/wk
  • max $12,602/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,400 when you book by Jun-10-2023**
" The villa was absolutely wonderful - elegant and comfortable, plenty of room for everyone. The outside spaces were fantastic (if a bit buggy). The location was ide..." - Mary
Save $1,849 Photo of Beautiful Tuscan Villa on a Large Estate
  • $18,485/wk
  • $16,637/wk
  • Min Stay: 7 days
Sleeps 29 people
  • 5 single bedrooms
  • 12 double bedrooms
  • 16 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
** Save up to $1,849 when you book by Jun-10-2023**
  • Enquire for Rates
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Enquire for Rates
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Good...." - Randee
  • Enquire for Rates
Sleeps 8 to 9 people
  • 4 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" We had a very pleasant stay and would recommend the property...." - Amy
Save $140 Photo of Holiday Accommodation in Chianti
  • $1,401/wk
  • $1,261/wk
  • Min Stay: 7 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $140 when you book by Jun-10-2023**
" Fantastic place with beautiful views, very secluded and quiet. Great and very large covered outdoor patio...." - Liz
Save $140 Photo of Holiday Accommodation in Chianti
  • $1,401/wk
  • $1,261/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $140 when you book by Jun-10-2023**
" Fantastic! Just as great as I thought it would be! The outdoor pool seating areas were amazing...." - Mary Ann
Save $140 Photo of Holiday Accommodation in Chianti
  • $1,401/wk
  • $1,261/wk
  • Min Stay: 7 days
Sleeps 5 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $140 when you book by Jun-10-2023**
" It was an amazing vacation with our family in this beautiful setting. Our host Leonardo was extremely gracious and very accommodating...." - Diana
  • Enquire for Rates
Sleeps 8 to 10 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" The property is beautiful! The view is amazing and you wake up every morning to a symphony of birds and frogs. The villa itself is rustic but nice and very comfo..." - Lisa
  • Enquire for Rates
Sleeps 10 to 12 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Enquire for Rates
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
" We had a great time at Poggio 2. Giulia was very helpful ..." - Karyn
  • Enquire for Rates
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" 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
  • Enquire for Rates
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
  • Air Conditioning
Save $616 Photo of Tuscany Villa Rental near Greve
  • min $3,501/wk
  • max $6,161/wk
  • min $3,151/wk
  • max $5,545/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $616 when you book by Jun-10-2023**
" Our stay was the highlight of our trip to Italy. ..." - Patty
  • Enquire for Rates
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" Superb villa. Probably Top Ten in Tuscany and Top Five for large groups...." - Samuel
Save $429 Photo of Farmhouse Rental in Tuscany, Castelfiorentino
  • $4,289/wk
  • $3,860/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $429 when you book by Jun-10-2023**
" We had a delightful week at this villa. We were very satisfied and happy. We appreciated the security of being able to park off the street and within a gated pro..." - Katherine
  • Enquire for Rates
Sleeps 16 to 18 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Fabulous...." - Austin
Save $935 Photo of Villa Rental in Tuscany, San Donato in Poggio
  • min $5,617/wk
  • max $9,350/wk
  • min $5,055/wk
  • max $8,415/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $935 when you book by Jun-10-2023**
" Very relaxing, peaceful, in a beautiful setting. ..." - Louise
  • Enquire for Rates
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" We had a wonderful time. The house was beautiful and everything we expected. ..." - Theresa
  • Enquire for Rates
Sleeps 8 people
  • 4 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" Fantastic. We love this place ..." - Linda
  • Enquire for Rates
Sleeps 36 to 56 people
  • 18 double bedrooms
  • 11 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
Save $2,888 Photo of Self Catering Accommodation in Tuscany
  • $9,627/wk
  • $8,664/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $2,888 when you book by Jun-10-2023**
" Overall experience was wonderful. Gabriella, the manager, was well-informed and provided great insight as to local restaurants, local markets, local stores and tr..." - Dorothy
  • Enquire for Rates
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
" An experience of a lifetime! Fantastic from any angle or view! ..." - Karen
  • Enquire for Rates
Sleeps 80 to 120 people
  • 1 single bedrooms
  • 42 double bedrooms
  • 35 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
Save $683 Photo of Two Chianti Farmhouses for Large Group on a Wine Estate
  • min $3,501/wk
  • max $6,826/wk
  • min $3,151/wk
  • max $6,143/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $683 when you book by Jun-10-2023**
" I don't think we even dreamed that staying at this villa would be the experience it turned into a truly once-in-a-lifetime experience when family could all com..." - Keith
  • Enquire for Rates
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" We loved this hunter's cottage! The property manager couldn't have been more helpful. The pool was a delight and the property was lovely with an eclectic a..." - Jane
Save $149 Photo of Walk To Small Town for Cappuccino in Tuscany
  • min $928/wk
  • max $1,488/wk
  • min $835/wk
  • max $1,339/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 $149 when you book by Jun-10-2023**
" It was an experience of a lifetime - just awesome!..." - Carmita
 
Displaying 1 to 30 of 132 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..