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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 $2,174/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 $455 when you book by Jun-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 Jun-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 Botticelli - 22076: 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 Jun-20-2021**
5.0 stars
2 reviews
" Wonderful..." - Aline
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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 Jun-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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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 Jun-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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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 Jun-20-2021**
5.0 stars
5 reviews
" Terrific!..." - Ross
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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 Jun-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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Casetta Ombra - 14745: Tuscany Vacation Villa

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  • min $1,961/wk
  • max $2,521/wk
  • min $1,765/wk
  • max $2,269/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
  • Air Conditioning
** Save up to $252 when you book by Jun-20-2021**
5.0 stars
2 reviews
" It was wonderful. ..." - Cathie
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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 Jun-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 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 Jun-20-2021**
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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 Jun-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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  • min $3,793/wk
  • max $6,264/wk
  • min $3,414/wk
  • max $5,638/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $626 when you book by Jun-20-2021**
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San Barberino 3 - 18412: Walk To Small Town for Cappuccino in Tuscany

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  • 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 Jun-20-2021**
5.0 stars
35 reviews
" It was an experience of a lifetime - just awesome!..." - Carmita
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Villa Niccolo - 18895: 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 Jun-20-2021**
4.0 stars
2 reviews
" Lovely, relaxing stay with easy access to onsite property managers. ..." - Katie
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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 $20,863/wk
  • min $11,972/wk
  • max $18,777/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $5,842 when you book by Jun-20-2021**
5.0 stars
3 reviews
" Fantastic. 13 adults. Accommodations outstanding and the view is idyllic...." - Joan
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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 Jun-20-2021**
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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 Jun-20-2021**
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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 Jun-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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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 Jun-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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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 Jun-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 Jun-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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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 Jun-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 Jun-20-2021**
5.0 stars
2 reviews
" Wonderful...." - Naomi
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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 Jun-20-2021**
5.0 stars
8 reviews
" Wonderful!..." - Chuck
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Rustici 8 - 20413: Ancient Hamlet in Tuscany near Florence

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  • min $931/wk
  • max $1,274/wk
  • min $838/wk
  • max $1,147/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $127 when you book by Jun-20-2021**
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Terme - Mia - 22072: Apartment Rental in Tuscany, Gambassi Terme

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  • min $1,732/wk
  • max $2,132/wk
  • min $1,559/wk
  • max $1,919/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $213 when you book by Jun-20-2021**
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Terme - Lilla - 22074: Apartment Rental in Tuscany, Gambassi Terme

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  • min $1,292/wk
  • max $1,691/wk
  • min $1,163/wk
  • max $1,522/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Air Conditioning
** Save up to $169 when you book by Jun-20-2021**
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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 Jun-20-2021**
3.0 stars
1 reviews
" The setting is very quaint. ..." - Mike
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Rustici 6 - 20411: 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 Jun-20-2021**
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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 Jun-20-2021**
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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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