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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 146 villas
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Villa Botticelli - 22076: Villa Rental in Tuscany, San Donato in Poggio

Save $839 Photo of Villa Rental in Tuscany, San Donato in Poggio
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  • 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 Jan-31-2022**
5.0 stars
6 reviews
" Wonderful..." - Aline
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Poggio Antico - 15365: Villa Rental Chianti Tuscany Near Florence

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  • min $2,415/wk
  • max $4,554/wk
  • min $2,174/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 Jan-31-2022**
5.0 stars
183 reviews
" We had a wonderful time. The house was beautiful and everything we expected. ..." - Theresa
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Villa Lisetta - 21996: Charming, traditional Tuscan villa with pool, terrace with views, located in Montaione

Save $671 Photo of Charming, traditional Tuscan villa with pool, terrace with views, located in Montaione
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  • min $4,517/wk
  • max $6,709/wk
  • min $4,065/wk
  • max $6,038/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $671 when you book by Jan-31-2022**
5.0 stars
2 reviews
" Fantastic. We love this place ..." - Linda
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San Barberino 3 - 18412: Walk To Small Town for Cappuccino in Tuscany

Save $181 Photo of Walk To Small Town for Cappuccino in Tuscany
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  • min $1,046/wk
  • max $1,811/wk
  • min $941/wk
  • max $1,630/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 $181 when you book by Jan-31-2022**
5.0 stars
35 reviews
" It was an experience of a lifetime - just awesome!..." - Carmita
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Certaldo 4 - 20540: One of Four Apartments on Large Tuscan Estate

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  • min $1,811/wk
  • max $2,615/wk
  • min $1,630/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 Jan-31-2022**
5.0 stars
3 reviews
" Our stay was everything we wanted and more. We loved everything about this beautiful and peaceful property. The views were breathtaking. Gina the caretaker was ..." - Denise
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Villa Elettra - 21614: Lovely Tuscan Villa with Swimming Pool and Views

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  • min $1,961/wk
  • max $4,481/wk
  • min $1,765/wk
  • max $4,033/wk
  • Min Stay: 7 days
Sleeps 8 to 10 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $448 when you book by Jan-31-2022**
4.5 stars
3 reviews
" 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
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Villa Cacciatore - 14743: Self Catering Accommodation in Tuscany

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  • min $6,721/wk
  • max $10,502/wk
  • min $6,049/wk
  • max $9,452/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 Jan-31-2022**
4.5 stars
12 reviews
" 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
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Il Castello - 19184: Castle Rental in Tuscany, Montespertoli (Chianti Area)

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  • Enquire for Rates
Sleeps 80 to 120 people
  • 1 single bedrooms
  • 42 double bedrooms
  • 35 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
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Casa del Grano - 20310: Chianti Farmhouse on a Wine Estate

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  • min $1,494/wk
  • max $2,988/wk
  • min $1,345/wk
  • max $2,689/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $299 when you book by Jan-31-2022**
4.5 stars
4 reviews
" It is a beautiful setting for a relaxed vacation...." - ANNAMMA
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San Barberino 2 - 18411: Charming Apartment in Chianti Overlooking the Countryside

Save $181 Photo of Charming Apartment in Chianti Overlooking the Countryside
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  • min $1,046/wk
  • max $1,811/wk
  • min $941/wk
  • max $1,630/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 $181 when you book by Jan-31-2022**
5.0 stars
24 reviews
" The view and being in a small town. ..." - Joseph
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Villa Adelia - 21607: Tuscan Villa with Gardens and Pool for a Family

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  • min $1,961/wk
  • max $4,481/wk
  • min $1,765/wk
  • max $4,033/wk
  • Min Stay: 7 days
Sleeps 8 to 9 people
  • 4 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $448 when you book by Jan-31-2022**
3.0 stars
1 reviews
" The setting is very quaint. ..." - Mike
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Toni 4 - 18535: Holiday Accommodation in Chianti

Save $154 Photo of Holiday Accommodation in Chianti
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  • min $771/wk
  • max $1,541/wk
  • min $694/wk
  • max $1,387/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $154 when you book by Jan-31-2022**
5.0 stars
14 reviews
" The people managing the property are first class. Very conscientious and helpful. ..." - Bo
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Casa Gilda - 20918: Tuscan Farmhouse Rental on Large Estate

Save $613 Photo of Tuscan Farmhouse Rental on Large Estate
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  • min $4,551/wk
  • max $6,126/wk
  • min $4,096/wk
  • max $5,513/wk
  • Min Stay: 7 days
Sleeps 6 to 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $613 when you book by Jan-31-2022**
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Il Castello 14 - 7989: Tuscan Apartment in Historic Castle

Save $253 Photo of Tuscan Apartment in Historic Castle
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  • min $1,066/wk
  • max $2,532/wk
  • min $959/wk
  • max $2,279/wk
  • Min Stay: 3 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $253 when you book by Jan-31-2022**
4.5 stars
12 reviews
" It was comfortable, clean, and conveniently located. ..." - Misty
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Casa del Grano and Fieno - 19386: Two Chianti Farmhouses for Large Group on a Wine Estate

Save $598 Photo of Two Chianti Farmhouses for Large Group on a Wine Estate
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  • min $2,988/wk
  • max $5,975/wk
  • min $2,689/wk
  • max $5,378/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $598 when you book by Jan-31-2022**
5.0 stars
3 reviews
" 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
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San Barberino 1 - 18408: Apartment Rental in Chianti Tuscany

Save $336 Photo of Apartment Rental in Chianti Tuscany
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  • min $1,867/wk
  • max $3,361/wk
  • min $1,680/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 Jan-31-2022**
5.0 stars
23 reviews
" 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
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Certaldo 2 - 20538: One of Four Apartments on Large Tuscan Estate

Save $262 Photo of One of Four Apartments on Large Tuscan Estate
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  • min $1,811/wk
  • max $2,615/wk
  • min $1,630/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 Jan-31-2022**
5.0 stars
2 reviews
" Amazing place and a great location to explore the Tuscany region...." - Alex
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Villa Niccolo - 18895: Tuscany Villa on a Hill Close to Florence

Save $637 Photo of Tuscany Villa on a Hill Close to Florence
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  • 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 Jan-31-2022**
4.0 stars
2 reviews
" Lovely, relaxing stay with easy access to onsite property managers. ..." - Katie
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Il Castello 3 - 8004: Tuscan Apartment in Historic Castle

Save $208 Photo of Tuscan Apartment in Historic Castle
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  • 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 Jan-31-2022**
5.0 stars
6 reviews
" Terrific!..." - Ross
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Casa Geranio - 20021: Tuscany Villa with Private Pool

Save $329 Photo of Tuscany Villa with Private Pool
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  • min $1,708/wk
  • max $3,290/wk
  • min $1,537/wk
  • max $2,961/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $329 when you book by Jan-31-2022**
4.5 stars
8 reviews
" 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
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Casa Donnini - 20229: Tuscan Villa with a Private Pool in a Village

Save $398 Photo of Tuscan Villa with a Private Pool in a Village
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  • 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 Jan-31-2022**
4.5 stars
11 reviews
" Casa Donnini was absolutely wonderful. Great location. Pool. Store, bakery, butcher literally seconds away! A dream come true...." - Mark
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Il Castello 29 - 8001: Tuscan Apartment in Historic Castle

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  • min $887/wk
  • max $2,050/wk
  • min $798/wk
  • max $1,845/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $205 when you book by Jan-31-2022**
4.0 stars
2 reviews
" We'll be back...." - Tammy
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Il Castello 34 - 18747: Tuscan Apartment in Historic Castle

Save $166 Photo of Tuscan Apartment in Historic Castle
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  • 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 Jan-31-2022**
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Il Castello 27 - 7999: Tuscan Apartment in Historic Castle

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  • min $1,066/wk
  • max $2,191/wk
  • min $959/wk
  • max $1,972/wk
  • Min Stay: 3 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $219 when you book by Jan-31-2022**
5.0 stars
5 reviews
" 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
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Toni 2 - 18028: Holiday Accommodation in Chianti

Save $154 Photo of Holiday Accommodation in Chianti
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  • min $771/wk
  • max $1,541/wk
  • min $694/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 Jan-31-2022**
5.0 stars
7 reviews
" Fantastic! Just as great as I thought it would be! The outdoor pool seating areas were amazing...." - Mary Ann
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Villa Impruneta - 22246: Villa Rental in Tuscany, Impruneta

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  • min $6,797/wk
  • max $10,997/wk
  • min $6,117/wk
  • max $9,897/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,100 when you book by Jan-31-2022**
" We had a wonderful stay..." - Lilli
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Toni 1 - 18027: Holiday Accommodation in Chianti

Save $154 Photo of Holiday Accommodation in Chianti
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  • min $771/wk
  • max $1,541/wk
  • min $694/wk
  • max $1,387/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 $154 when you book by Jan-31-2022**
5.0 stars
14 reviews
" It was an amazing vacation with our family in this beautiful setting. Our host Leonardo was extremely gracious and very accommodating...." - Diana
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Casa Berto - 7895: Tuscany Farmhouse Close to a Castle

Save $370 Photo of Tuscany Farmhouse Close to a Castle
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  • min $1,420/wk
  • max $3,702/wk
  • min $1,278/wk
  • max $3,332/wk
  • Min Stay: 3 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $370 when you book by Jan-31-2022**
5.0 stars
7 reviews
" This location is perfectly situated for all the day trips we had planned, from Cinque Terre to Siena. ..." - Sadia
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Il Castello 28 - 8000: Tuscan Apartment in Historic Castle

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  • min $675/wk
  • max $1,559/wk
  • min $608/wk
  • max $1,403/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $156 when you book by Jan-31-2022**
4.5 stars
4 reviews
" Love this property. Second year in a row I have been there...." - Sadia
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Il Castello 33 - 18746: Tuscan Apartment in Historic Castle

Save $195 Photo of Tuscan Apartment in Historic Castle
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  • min $887/wk
  • max $1,952/wk
  • min $798/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 Jan-31-2022**
3.5 stars
2 reviews
" 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
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Displaying 1 to 30 of 146 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..

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