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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 165 villas
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Poggio Antico - 15365: Villa Rental Chianti Tuscany Near Florence

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  • min $2,415/wk
  • max $4,337/wk
  • min $1,739/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 $1,275 when you book by Apr-20-2021**
5.0 stars
181 reviews
" 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
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Donatella - 15152: Farmhouse Rental Near Certaldo, Tuscany

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  • 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 Apr-20-2021**
5.0 stars
150 reviews
" 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
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Villa Gialla - 14 - 19056: Beautiful Large Villa Close to Florence

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  • 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-20-2021**
5.0 stars
22 reviews
" It was an amazing experience. The property was lovely and we used the pool daily...." - Linda
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Villa Certaldo - 16414: Tuscany Villa Rental in Chianti

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  • min $3,016/wk
  • max $3,662/wk
  • min $2,714/wk
  • max $3,296/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $366 when you book by Apr-20-2021**
5.0 stars
117 reviews
" 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
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Villa Botticelli - 22076: Villa Rental in Tuscany, San Donato in Poggio

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  • min $4,760/wk
  • max $7,490/wk
  • min $4,284/wk
  • max $6,741/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $749 when you book by Apr-20-2021**
5.0 stars
2 reviews
" Wonderful..." - Aline
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Villa Pucci - 21045: Beautiful Tuscany Villa for a Large Group with Spectacular Views

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  • min $5,251/wk
  • max $12,077/wk
  • min $4,726/wk
  • max $10,869/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 $1,208 when you book by Apr-20-2021**
5.0 stars
9 reviews
" 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
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Villa Sella - 17118: Family-Friendly Villa Rental in Tuscany with Pool

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  • min $3,448/wk
  • max $4,093/wk
  • min $3,103/wk
  • max $3,684/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 $409 when you book by Apr-20-2021**
5.0 stars
131 reviews
" Wonderful all around!..." - Cinnamon
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Casetta Ombra - 14745: Tuscany Vacation Villa

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  • min $1,961/wk
  • max $3,326/wk
  • min $1,765/wk
  • max $2,993/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
  • Air Conditioning
** Save up to $333 when you book by Apr-20-2021**
5.0 stars
2 reviews
" It was wonderful. ..." - Cathie
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Il Castello 3 - 8004: Tuscan Apartment in Historic Castle

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  • min $884/wk
  • max $1,647/wk
  • min $796/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-20-2021**
5.0 stars
5 reviews
" Terrific!..." - Ross
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Villa Capannuccia - 14 - 18812: Large Villa in the Chianti Hills Close to Florence

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  • min $7,319/wk
  • max $11,152/wk
  • min $6,587/wk
  • max $10,037/wk
  • Min Stay: 4 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,115 when you book by Apr-20-2021**
5.0 stars
7 reviews
" The property is in a fabulous location with incredible 360 views- including a view to Florence. The house is over 500 years old but has been modernized with 7 bed..." - Robert
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Casale Rossella - 21732: Beautiful Tuscan Villa on a Large Estate

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  • min $5,880/wk
  • max $12,040/wk
  • min $5,292/wk
  • max $10,836/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 $1,204 when you book by Apr-20-2021**
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Villa Lisetta - 21996: Charming, traditional Tuscan villa with pool, terrace with views, located in Montaione

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  • $5,876/wk
  • $5,288/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $588 when you book by Apr-20-2021**
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Il Castello 34 - 18747: Tuscan Apartment in Historic Castle

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  • min $630/wk
  • max $1,315/wk
  • min $567/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-20-2021**
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Villa Capannuccia - 19 - 18811: Large Villa in Chianti Hills Close to Florence

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  • min $8,215/wk
  • max $12,712/wk
  • min $7,393/wk
  • max $11,441/wk
  • Min Stay: 4 days
Sleeps 19 people
  • 1 single bedrooms
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,271 when you book by Apr-20-2021**
5.0 stars
7 reviews
" This was one of the best large group trips we have ever taken. The place was far better than we expected. Paolo, the owner/architect was a charming guy who was t..." - Richard
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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 $1,050 when you book by Apr-20-2021**
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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Rustici 5 - 20410: Ancient Hamlet in Tuscany near Florence

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  • min $1,078/wk
  • max $1,421/wk
  • min $970/wk
  • max $1,279/wk
  • Min Stay: 7 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-20-2021**
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Villa Liona - 21132: Large Luxury Villa Rental in the Chianti with Spectacular Views

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  • min $13,302/wk
  • max $21,528/wk
  • min $11,972/wk
  • max $19,375/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $2,153 when you book by Apr-20-2021**
5.0 stars
3 reviews
" Fantastic. 13 adults. Accommodations outstanding and the view is idyllic...." - Joan
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Rustici 13 - 20418: Ancient Hamlet in Tuscany near Florence

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  • min $1,470/wk
  • max $1,960/wk
  • min $1,323/wk
  • max $1,764/wk
  • Min Stay: 7 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-20-2021**
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Rustici 9 - 20414: Ancient Hamlet in Tuscany near Florence

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  • min $1,078/wk
  • max $1,421/wk
  • min $970/wk
  • max $1,279/wk
  • Min Stay: 7 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-20-2021**
5.0 stars
1 reviews
" 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
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Casa Donnini - 20229: Tuscan Villa with a Private Pool in a Village

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  • min $924/wk
  • max $3,296/wk
  • min $832/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-20-2021**
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 31 - 8003: Tuscan Apartment in Historic Castle

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  • min $700/wk
  • max $1,699/wk
  • min $630/wk
  • max $1,529/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 single bedrooms
  • 1 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $170 when you book by Apr-20-2021**
4.0 stars
4 reviews
" Wonderful. A magnificent building in beautiful countryside. We rented 5 units - all in the out-buildings. I entered the same comments for all 5 units. ..." - Michael
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Villa Olga - 20950: Traditional Tuscan Villa on a Large Estate

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  • min $4,158/wk
  • max $9,660/wk
  • min $3,742/wk
  • max $8,694/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $966 when you book by Apr-20-2021**
5.0 stars
8 reviews
" Wonderful!..." - Chuck
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Rustici Estate - 21597: Ancient Hamlet in Tuscany near Florence

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  • min $21,952/wk
  • max $29,155/wk
  • min $19,757/wk
  • max $26,240/wk
  • Min Stay: 7 days
Sleeps 50 people
  • 25 double bedrooms
  • 25 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $2,916 when you book by Apr-20-2021**
5.0 stars
1 reviews
" 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
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Villa Betta - 20916: Beautiful Tuscan Villa on a Large Estate

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  • min $5,880/wk
  • max $13,860/wk
  • min $5,292/wk
  • max $12,474/wk
  • Min Stay: 7 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-20-2021**
5.0 stars
2 reviews
" Wonderful...." - Naomi
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Rustici 15 - 20420: Ancient Hamlet in Tuscany near Florence

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  • min $1,617/wk
  • max $2,107/wk
  • min $1,455/wk
  • max $1,896/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $211 when you book by Apr-20-2021**
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Poggio 2 - 19766: Tuscany Accommodation Within Walking Distance of Town

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  • min $1,512/wk
  • max $2,205/wk
  • min $1,361/wk
  • max $1,985/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
** Save up to $221 when you book by Apr-20-2021**
5.0 stars
6 reviews
" We had a great time at Poggio 2. Giulia was very helpful ..." - Karyn
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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 Apr-20-2021**
3.0 stars
1 reviews
" The setting is very quaint. ..." - Mike
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Rustici 4 - 20409: Ancient Hamlet in Tuscany near Florence

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  • min $1,078/wk
  • max $1,421/wk
  • min $970/wk
  • max $1,279/wk
  • Min Stay: 7 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-20-2021**
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Il Castello 13 - 7988: Tuscan Apartment in Historic Castle

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  • min $772/wk
  • max $1,392/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
5.0 stars
1 reviews
" 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
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Il Castello 33 - 18746: Tuscan Apartment in Historic Castle

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  • min $700/wk
  • max $1,545/wk
  • min $630/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-20-2021**
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 165 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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