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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 $2,573/wk
  • max $5,070/wk
  • min $2,316/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 Nov-30-2022**
" 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
Save $189 Photo of Tuscan Apartment in Historic Castle
  • min $1,125/wk
  • max $1,893/wk
  • min $1,013/wk
  • max $1,704/wk
  • Min Stay: 3 days
Sleeps 2 to 5 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $189 when you book by Nov-30-2022**
" Terrific!..." - Ross
Save $549 Photo of Beautiful Tuscan Villa on a Large Estate
  • $5,488/wk
  • $4,939/wk
  • Min Stay: 7 days
Sleeps 29 people
  • 5 single bedrooms
  • 12 double bedrooms
  • 15 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $549 when you book by Nov-30-2022**
Save $1,614 Photo of Villa Rental in Tuscany, Strada in Chianti
  • min $11,669/wk
  • max $16,142/wk
  • min $10,502/wk
  • max $14,528/wk
  • Min Stay: 7 days
Sleeps 20 people
  • 10 double bedrooms
  • 11 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
** Save up to $1,614 when you book by Nov-30-2022**
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 Nov-30-2022**
" 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
Save $186 Photo of Tuscan Apartment in Historic Castle
  • min $887/wk
  • max $1,864/wk
  • min $798/wk
  • max $1,678/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $186 when you book by Nov-30-2022**
Save $140 Photo of Holiday Accommodation in Chianti
  • min $841/wk
  • max $1,401/wk
  • min $757/wk
  • max $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 Nov-30-2022**
" Fantastic place with beautiful views, very secluded and quiet. Great and very large covered outdoor patio...." - Liz
Save $124 Photo of Tuscan Apartment in Historic Castle
  • min $622/wk
  • max $1,242/wk
  • min $560/wk
  • max $1,118/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $124 when you book by Nov-30-2022**
Save $213 Photo of Tuscan Apartment in Historic Castle
  • min $978/wk
  • max $2,128/wk
  • min $880/wk
  • max $1,915/wk
  • Min Stay: 3 days
Sleeps 5 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $213 when you book by Nov-30-2022**
Save $160 Photo of Tuscan Apartment in Historic Castle
  • min $887/wk
  • max $1,599/wk
  • min $798/wk
  • max $1,439/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $160 when you book by Nov-30-2022**
" We had a delightful time at the castle. The apartment was lovely and well maintained. The castle was very scenic...." - Joan
Save $160 Photo of Tuscan Apartment in Historic Castle
  • min $787/wk
  • max $1,599/wk
  • min $708/wk
  • max $1,439/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $160 when you book by Nov-30-2022**
Save $210 Photo of Tuscan Apartment in Historic Castle
  • min $1,155/wk
  • max $2,096/wk
  • min $1,040/wk
  • max $1,886/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $210 when you book by Nov-30-2022**
Save $163 Photo of Tuscan Apartment in Historic Castle
  • min $1,126/wk
  • max $1,629/wk
  • min $1,013/wk
  • max $1,466/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $163 when you book by Nov-30-2022**
Save $189 Photo of Tuscan Apartment in Historic Castle
  • min $899/wk
  • max $1,893/wk
  • min $809/wk
  • max $1,704/wk
  • Min Stay: 3 days
Sleeps 3 to 4 people
  • 1 single bedrooms
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $189 when you book by Nov-30-2022**
Save $142 Photo of Tuscan Apartment in Historic Castle
  • min $675/wk
  • max $1,420/wk
  • min $608/wk
  • max $1,278/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $142 when you book by Nov-30-2022**
Save $171 Photo of CastleApartment Rental in Tuscany, Montagnana
  • min $999/wk
  • max $1,708/wk
  • min $899/wk
  • max $1,537/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $171 when you book by Nov-30-2022**
" Outstanding! The property and the villa were absolutely perfect and everything we hoped it would be!..." - Dana
Save $189 Photo of Tuscan Apartment in Historic Castle
  • min $1,179/wk
  • max $1,893/wk
  • min $1,061/wk
  • max $1,704/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $189 when you book by Nov-30-2022**
" Driving up to the Castle was a surreal experience. It looks like a castle from a story book. The frescoes were everywhere, including the entire room. It made fo..." - Lauren
Save $160 Photo of Tuscan Apartment in Historic Castle
  • min $985/wk
  • max $1,599/wk
  • min $887/wk
  • max $1,439/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $160 when you book by Nov-30-2022**
" 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 $153 Photo of Tuscan Apartment in Historic Castle
  • min $782/wk
  • max $1,526/wk
  • min $704/wk
  • max $1,373/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $153 when you book by Nov-30-2022**
" The castle is beautiful...." - Serena
Save $144 Photo of Tuscan Apartment in Historic Castle
  • min $878/wk
  • max $1,438/wk
  • min $790/wk
  • max $1,294/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $144 when you book by Nov-30-2022**
" Ambiance. Staff was very good...." - Will
Save $202 Photo of Tuscan Apartment in Historic Castle
  • min $887/wk
  • max $2,023/wk
  • min $798/wk
  • max $1,821/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $202 when you book by Nov-30-2022**
" We thoroughly enjoyed our stay and the property was very well-maintained. We would recommend staying here to others. We quickly realized, however, that some of the..." - Wendy
Save $216 Photo of Tuscan Apartment in Historic Castle
  • min $1,106/wk
  • max $2,159/wk
  • min $995/wk
  • max $1,943/wk
  • Min Stay: 3 days
Sleeps 4 to 6 people
  • 3 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $216 when you book by Nov-30-2022**
" Very good. However, it was 104 most days and didn't cool off much at night. Good home base for day trips...." - Kelly
Save $142 Photo of Tuscan Apartment in Historic Castle
  • min $675/wk
  • max $1,420/wk
  • min $608/wk
  • max $1,278/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $142 when you book by Nov-30-2022**
" Love this property. Second year in a row I have been there...." - Sadia
Save $195 Photo of Tuscan Apartment in Historic Castle
  • min $1,066/wk
  • max $1,952/wk
  • min $959/wk
  • max $1,757/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $195 when you book by Nov-30-2022**
" Beautiful, large castle in a picture perfect location that seemed like something out of a Tuscan fantasy. ..." - Deborah
Save $140 Photo of Holiday Accommodation in Chianti
  • min $841/wk
  • max $1,401/wk
  • min $757/wk
  • max $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 Nov-30-2022**
" Fantastic! Just as great as I thought it would be! The outdoor pool seating areas were amazing...." - Mary Ann
Save $1,849 Photo of Beautiful Tuscan Villa on a Large Estate
  • min $7,000/wk
  • max $18,485/wk
  • min $6,300/wk
  • max $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 Nov-30-2022**
Save $300 Photo of Tuscan Apartment in Historic Castle
  • min $1,671/wk
  • max $3,002/wk
  • min $1,504/wk
  • max $2,702/wk
  • Min Stay: 3 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $300 when you book by Nov-30-2022**
" Overall our stay at the villa was a wonderful experience and the views amazing. Just wish we could have stayed around long enough to enjoy more!..." - Anne
Save $1,323 Photo of Private Villa on a Castle Estate near Certaldo
  • min $9,102/wk
  • max $13,232/wk
  • min $8,192/wk
  • max $11,909/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,323 when you book by Nov-30-2022**
" 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 $201 Photo of Tuscan Apartment in Historic Castle
  • min $903/wk
  • max $2,014/wk
  • min $813/wk
  • max $1,813/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $201 when you book by Nov-30-2022**
Save $210 Photo of Tuscan Apartment in Historic Castle
  • min $1,287/wk
  • max $2,096/wk
  • min $1,158/wk
  • max $1,886/wk
  • Min Stay: 3 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $210 when you book by Nov-30-2022**
 
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..