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Chianti Villa Rentals Tuscany, Italy

North of Siena 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 63 villas
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Villa Dora - 21028: Villa on Large Estate Near San Gimignano

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  • min $4,500/wk
  • max $9,300/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
5.0 stars
16 reviews
" We had a wonderful time at the villa. Everything about the villa and property exceeded our expectations. The grounds at this time of the year were breathtaking wit..." - Eileen
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Vecchio Borgo - Pascolo - 15438: Apartment Farmhouse in Tuscany

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  • min $932/wk
  • max $1,177/wk
  • Min Stay: 4 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
5.0 stars
51 reviews
" Fantastic!!! This was our 4th time to return! Loved it and love Claudia, Rudi and Simone!..." - Dana
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Villa Del Cielo with Caminetto - 9845: Tuscany Villa near Siena with Private Pool

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  • min $1,868/wk
  • max $7,293/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 2 single bedrooms
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
5.0 stars
72 reviews
" Very good. The property management had lots of cheeses, meats, bread and wine for us upon arrival. Both kitchens were well stocked with glassware, dishes, pots an..." - Johnnie Lynn
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Vecchio Borgo - Mensola - 15437: Restored Farmhouse Surrounded by Vineyards and Olive Groves, Centrally Located in Tuscany

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  • min $1,762/wk
  • max $2,521/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
5.0 stars
87 reviews
" Great. Claudia and Rudi terrific ..." - Frank
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Regina - 21173: Apartment in Siena Overlooking the Famous Piazza del Campo

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  • min $2,087/wk
  • max $3,399/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
4.5 stars
2 reviews
" Very good...." - Kenneth
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Vecchio Borgo - Piscina - 15439: Tuscany Holiday Apartment

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  • min $932/wk
  • max $1,177/wk
  • Min Stay: 4 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
5.0 stars
25 reviews
" Absolutely wonderful. Experience enhanced by the warm hospitality of Claudia and Rudy - we left feeling like family friends not hospitality guests...." - Kay
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Vecchio Borgo - Bella Vista - 15435: Vacation Rental Agritourism in Tuscany

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  • min $1,520/wk
  • max $1,814/wk
  • Min Stay: 4 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
5.0 stars
48 reviews
" Beautiful property, apartment well-appointed. Claudia and Rudi very friendly and helpful finding local eateries, grocery stores. Very quiet and although we were ..." - Susan
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Casa Susanna - 21812: Country Villa in heart of Chianti centrally located close to regions’ history, art, restaurants.

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  • min $840/wk
  • max $1,881/wk
  • Min Stay: 7 days
Sleeps 3 to 5 people
  • 1 single bedrooms
  • 1 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
5.0 stars
1 reviews
" The property manager was a gem. The garden was so wonderful. Very inviting place and it was so convenient to go to Siena and so many wineries. One of the best v..." - Harold
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Contrada - 21302: Apartment Rental in the Center of Siena

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  • min $2,352/wk
  • max $4,587/wk
  • Min Stay: 3 days
Sleeps 5 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Washing Machine
  • Maid Service
  • Air Conditioning
4.0 stars
1 reviews
" Very good to excellent. The manager was very good... location was amazing, apartment was very comfortable. ..." - Mar
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Villa Valeria - 21623: Large Chianti Classico Villa with Swimming Pool and Spa near Siena

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  • min $11,611/wk
  • max $12,850/wk
  • Min Stay: 3 days
Sleeps 18 people
  • 9 double bedrooms
  • 10 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
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Villa Castellina - 20544: Large Farmhouse on a Wine Estate near Siena Fit for Families

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  • min $5,511/wk
  • max $9,665/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
5.0 stars
2 reviews
" Villa Castellina is unbelievably wonderful. It went beyond my wildest imagination. The views were spectacular, modern, comfortable. All of us were so pleased, e..." - Pamela T
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Villa Adelina - 18921: Farmhouse Rental in Chianti Area of Tuscany

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  • min $2,914/wk
  • max $6,698/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
5.0 stars
19 reviews
" We had a wonderful time at Villa Adelina. The rooms were large and we thought it was great that everyone had their own bathroom. I don't know how it compares..." - Patricia
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Terra di Siena 1 - 16780: Family-Friendly Apartment Close to Siena

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  • min $1,079/wk
  • max $2,162/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
4.0 stars
17 reviews
" Overall the property and atmosphere were great. The location was convenient to Siena and we found this to be very enjoyable, much more so than Florence...." - Peter
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Villa Celestina - 21797: Elegant San Gimignano Villa with Pool near historical sites, art museums.

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  • min $3,890/wk
  • max $6,125/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
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Monteriggioni - La Villa - 13961: Beautiful Historic Villa Near Monteriggioni in Tuscany

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  • min $8,629/wk
  • max $10,935/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
5.0 stars
1 reviews
" I would and already have recommended the villa to anyone. My experience with your firm was excellent. When I return to Tuscany I intend to stay at the same locatio..." - Hal
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Villa Riccardo - 20621: Beautiful Chianti Villa with Guest Cottage and Private Infinity Pool

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  • min $9,522/wk
  • max $12,602/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
4.5 stars
6 reviews
" It was fantastic. ..." - Jessica
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Casa Elsa - 20501: Farmhouse in the Chianti Region for Friends or a Large Family

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  • min $4,138/wk
  • max $8,292/wk
  • Min Stay: 7 days
Sleeps 11 people
  • 1 single bedrooms
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
5.0 stars
1 reviews
" Terrific! Everything worked, the villa was comfortable and very clean, and it was wonderful to be out in the countryside and simultaneously next to a substantiall..." - Alexander
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Tulipano - 21907: House Rental in Tuscany, Siena

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  • min $1,050/wk
  • max $1,239/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 bathrooms
  • Independent House
  • Maid Service
  • Air Conditioning
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Vecchio Borgo - Quercia - 15440: Farmhouse Accommodation in Tuscany

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  • min $961/wk
  • max $1,230/wk
  • Min Stay: 4 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
5.0 stars
33 reviews
" Beautiful stay...." - Joan
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Vecchio Borgo - Piccola - 15436: Tuscany Vacation Rental Agritourism

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  • min $961/wk
  • max $1,230/wk
  • Min Stay: 4 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
5.0 stars
20 reviews
" This was my second visit in five months! I love it!..." - Barbara
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Rosalia 1 - 18903: Farmhouse Rental in Tuscany, Castellina Scalo

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  • min $1,871/wk
  • max $4,061/wk
  • Min Stay: 7 days
Sleeps 9 people
  • 1 single bedrooms
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
4.5 stars
5 reviews
" Very nice and restful. S..." - Olenka
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Casa del Mulino with Guesthouse - 14847: Charming Villa with Pool in Tuscany

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  • min $3,641/wk
  • max $5,601/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
4.5 stars
24 reviews
" Very Good. A little too far from grocery store and Florence...." - Mary
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Rosalia 2 - 18904: Farmhouse Rental in Tuscany, Castellina Scalo

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  • min $1,200/wk
  • max $2,602/wk
  • Min Stay: 7 days
Sleeps 7 people
  • 1 single bedrooms
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
4.5 stars
11 reviews
" Overall, we absolutely loved our stay at this property. It was beautiful, quiet, close to many things that we wanted to see, and a perfect mix of relaxation and b..." - Lisa
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Casa del Mulino - 14852: Chianti Tuscany Villa Rental, Near Siena

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  • min $3,186/wk
  • max $4,901/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
5.0 stars
35 reviews
" We had a wonderful time at the property..." - Leo
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Rosalia 3 - 18905: Farmhouse Rental in Tuscany, Castellina Scalo

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  • min $1,374/wk
  • max $2,987/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
5.0 stars
5 reviews
" Rosalia 3 is an excellent property if you are looking to spend an authentic week in the Tuscan countryside. Located in a very private setting on a wine estate, th..." - Lisa
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Terra di Siena 3 - 16782: Family-Friendly Apartment Close to Siena

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  • min $981/wk
  • max $1,565/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
4.0 stars
7 reviews
" The time spent at Terra di Siena was wonderful and I would go back in a heartbeat...." - Vallerie
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Villa Mora with Guest House - 21229: Large Villa with Pool and Guest House in Chianti

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  • min $9,012/wk
  • max $15,628/wk
  • Min Stay: 7 days
Sleeps 14 to 18 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
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Terra di Siena 10 - 17683: Family-Friendly Farmhouse Close to Siena

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  • min $1,275/wk
  • max $2,573/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
3.0 stars
10 reviews
" The view of the hills, grape orchard, and olive trees...." - Ann
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Prima Casa - 19898: Chianti Villa near a Charming Village

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  • min $5,146/wk
  • max $11,272/wk
  • Min Stay: 3 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
5.0 stars
14 reviews
" Everything was fine...." - William
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Casa Luciana - 18919: Farmhouse Rental in Chianti Area of Tuscany

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  • min $2,914/wk
  • max $6,698/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
5.0 stars
22 reviews
" Very nice place well worth the money...." - Brad
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Displaying 1 to 30 of 63 villas

Following the old Chiantigiana road from your Chianti vacation rental you see the heart of this region, including the Chianti Classico, the Sienese Chianti, and southeast of Siena, the border of Valdarno. To the north lies San Casciano, and further north still, Florence. What to do while staying in one of our villas in 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. View our Rental Villas in North Siena..

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