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Tuscany Villas Under The Tuscan Sun

You've dreamt of the rolling Tuscan hills; glasses of ruby-red Classico; villas framed with the orange glow of the setting sun; medieval hill towns outlined on the horizon... So come experience Italian life at its best, under the Tuscan sun. 

Displaying 1 to 30 of 56 villas
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Poggio Antico - 15365: Villa Rental Chianti Tuscany Near Florence

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  • min $2,190/wk
  • max $4,337/wk
  • min $1,971/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 $434 when you book by Oct-20-2019**
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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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 Oct-20-2019**
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 $2,077/wk
  • max $3,558/wk
  • min $1,495/wk
  • max $3,202/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $996 when you book by Oct-20-2019**
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 Dora - 21028: Villa on Large Estate Near San Gimignano

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  • min $5,300/wk
  • max $9,300/wk
  • min $4,770/wk
  • max $8,370/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $2,580 when you book by Oct-20-2019**
5.0 stars
27 reviews
" Villa Dora exceeded our expectations in every way! We were a family of 6 adults and every one of us fell in love with the villa!..." - Lynn
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Villa Brunello - 20520: Spacious and Beautiful Tuscany Villa Near Montalcino

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  • min $8,432/wk
  • max $13,889/wk
  • min $7,589/wk
  • max $12,500/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,389 when you book by Oct-20-2019**
4.0 stars
1 reviews
" Relaxing We loved it. The stunning views really made us know we were in Tuscany...probably the most beautiful part of Tuscany. Although narrow winding dirt roads ..." - Val
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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 $1,586/wk
  • max $2,269/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $252 when you book by Oct-20-2019**
5.0 stars
87 reviews
" Great. Claudia and Rudi terrific ..." - Frank
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Antonietta - 18031: Tuscany Villa Rental near Greve

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  • min $2,941/wk
  • max $5,601/wk
  • min $2,647/wk
  • max $5,041/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $560 when you book by Oct-20-2019**
5.0 stars
92 reviews
" Our stay was the highlight of our trip to Italy. ..." - Patty
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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 $1,368/wk
  • max $1,633/wk
  • Min Stay: 4 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $181 when you book by Oct-20-2019**
5.0 stars
49 reviews
" A wonderful place to relax...." - Ruth
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Podere della Fraternita - 17413: Tuscany Villa with Four Bedrooms all with En Suite Baths

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  • min $3,000/wk
  • max $4,961/wk
  • min $2,430/wk
  • max $4,465/wk
  • Min Stay: 7 days
Sleeps 8 to 10 people
  • 4 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $943 when you book by Oct-20-2019**
5.0 stars
50 reviews
" Truly excellent. The only thing that could have been better would have been the weather...." - James
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Villa Gialla - 20 - 18986: Large Villa Rental in Tuscany Near Florence with Pool

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  • min $6,721/wk
  • max $9,708/wk
  • min $6,049/wk
  • max $8,737/wk
  • Min Stay: 5 days
Sleeps 20 people
  • 2 single bedrooms
  • 9 double bedrooms
  • 11 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $971 when you book by Oct-20-2019**
5.0 stars
19 reviews
" A wonderful two weeks was thoroughly enjoyed by our entire family of 20 people aged from 4 years up to 70 years. Facilities were excellent in every respect and ass..." - Terry
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Villa Andreina - 14 - 19058: Lovely Villa with Countryside Views of Tuscany

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  • min $3,493/wk
  • max $7,188/wk
  • min $3,144/wk
  • max $6,469/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $719 when you book by Oct-20-2019**
5.0 stars
14 reviews
" Perfect!..." - Michal
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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 $8,570/wk
  • max $11,342/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,260 when you book by Oct-20-2019**
4.5 stars
6 reviews
" It was fantastic. ..." - Jessica
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Villa Anita - 17233: Elegant countryside Tuscan villa with pool near historic town, restaurants, attractions.

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  • $6,763/wk
  • $6,087/wk
  • Min Stay: 7 days
Sleeps 8 to 9 people
  • 1 single bedrooms
  • 4 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $676 when you book by Oct-20-2019**
4.5 stars
4 reviews
" Absolutely fabulous! The views from every window and the expansive outdoor areas are breathtaking. The owner/host, Palmi, was accommodating, generous, thoughtful ..." - Eric
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Villa Del Cielo with Caminetto - 9845: Tuscany Villa near Siena with Private Pool

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  • min $3,338/wk
  • max $7,587/wk
  • min $3,004/wk
  • max $6,828/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
** Save up to $759 when you book by Oct-20-2019**
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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Villa Lucchesia - 20184: Historic 16th Century Villa in Tuscany with Private Pool and Shared Tennis Court

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  • min $7,060/wk
  • max $11,377/wk
  • min $6,354/wk
  • max $10,239/wk
  • Min Stay: 4 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
** Save up to $1,138 when you book by Oct-20-2019**
5.0 stars
14 reviews
" Of all the lovely places I've been, it's the one I most want to return to. Sooo relaxing--because of the peaceful, beautiful surroundings, the beauty of th..." - Anne
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Villa Senese - 20932: Luxury Villa Rental Near Siena

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  • min $19,603/wk
  • max $22,403/wk
  • min $17,643/wk
  • max $20,163/wk
  • Min Stay: 7 days
Sleeps 25 people
  • 3 single bedrooms
  • 11 double bedrooms
  • 14 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $2,240 when you book by Oct-20-2019**
5.0 stars
3 reviews
" The villa was lovely...." - Phyllis
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Villa Gaia - 21547: Tuscan Farmhouse with Private Pool and Beautiful Views

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  • min $5,880/wk
  • max $9,016/wk
  • min $5,292/wk
  • max $8,114/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $902 when you book by Oct-20-2019**
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Villa Orfea - 22311: Umbrian Villa for 14 with Pool, Views, Social Area Perfect for Wedding and Reunions!

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  • min $2,696/wk
  • max $5,146/wk
  • min $2,382/wk
  • max $4,631/wk
  • Min Stay: 4 days
Sleeps 14 people
  • 7 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $633 when you book by Oct-20-2019**
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Vittoria Estate - 21883: Large Resort Estate in Umbria Ideal for Large Groups

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  • min $15,122/wk
  • max $23,733/wk
  • min $13,610/wk
  • max $21,360/wk
  • Min Stay: 3 days
Sleeps 26 people
  • 13 double bedrooms
  • 13 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $2,373 when you book by Oct-20-2019**
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Villa Collina - 22204: Exclusive Hilltop Medieval Villa Features Modern Comforts, Panoramic Sea Views, Garden, Pool and Jacuzzi in Pistoia, Tuscany

Save $906 Photo of Exclusive Hilltop Medieval Villa Features Modern Comforts, Panoramic Sea Views, Garden, Pool and Jacuzzi in Pistoia, Tuscany
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  • min $2,661/wk
  • max $6,021/wk
  • min $2,258/wk
  • max $5,419/wk
  • Min Stay: 7 days
Sleeps 10 to 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $906 when you book by Oct-20-2019**
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Villa Grandiosa - 20457: Private Villa on a Castle Estate near Certaldo

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  • min $10,922/wk
  • max $13,582/wk
  • min $9,830/wk
  • max $12,224/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,358 when you book by Oct-20-2019**
5.0 stars
3 reviews
" 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
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Girasole - 20 - 21309: Villa with Pool and 2 Guesthouses for a Group in Eastern Tuscany

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  • min $7,869/wk
  • max $12,696/wk
  • min $6,836/wk
  • max $11,426/wk
  • Min Stay: 7 days
Sleeps 13 to 20 people
  • 7 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,987 when you book by Oct-20-2019**
5.0 stars
4 reviews
" Wonderful! We had a group of 15, and everyone agrees that this villa and hostess are superior. We were there two weeks, and each day was better than the one before..." - Pamela
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La Solaia - 20434: Villa in Tuscany Near Certaldo and the Chianti Region

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  • min $1,888/wk
  • max $3,235/wk
  • min $1,359/wk
  • max $2,912/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $906 when you book by Oct-20-2019**
5.0 stars
47 reviews
" Our experience was very soul-refreshing with the family at La Solaia. We enjoyed the location and the home. The kitchen was stocked with enough basic equipment to ..." - Dana
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Villa Sella - 17118: Family-Friendly Villa Rental in Tuscany with Pool

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  • min $2,293/wk
  • max $3,963/wk
  • min $1,651/wk
  • max $3,567/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 $1,110 when you book by Oct-20-2019**
5.0 stars
129 reviews
" Wonderful all around!..." - Cinnamon
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Villa Alessandro - 16485: Beautiful Hilltop Villa in Tuscany with Spectacular Views

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  • min $4,621/wk
  • max $11,062/wk
  • min $4,159/wk
  • max $9,956/wk
  • Min Stay: 7 days
Sleeps 13 to 18 people
  • 1 single bedrooms
  • 6 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,106 when you book by Oct-20-2019**
5.0 stars
31 reviews
" Our group cherishes relationships and therefore thoughtfulness, condsideration and a desire to serve are a valuable component of our friendships. Upon meeting Ale..." - Mark
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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 $13,228/wk
  • min $7,393/wk
  • max $11,905/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 $1,323 when you book by Oct-20-2019**
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 Capannuccia - 14 - 18812: Large Villa in the Chianti Hills Close to Florence

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  • min $7,319/wk
  • max $11,603/wk
  • min $6,587/wk
  • max $10,443/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 $1,160 when you book by Oct-20-2019**
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 Filippo - 20058: Villa Near Cortona with a Private Pool

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  • min $3,003/wk
  • max $4,900/wk
  • min $2,703/wk
  • max $4,410/wk
  • Min Stay: 7 days
Sleeps 9 people
  • 1 single bedrooms
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $490 when you book by Oct-20-2019**
4.0 stars
2 reviews
" We loved our villa! The home was a vision of what, in our minds, Tuscany would look like. It was so comfortable and perfect for our stay. Louisa was darling and ..." - Cindy
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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 Oct-20-2019**
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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Villa Sasso - 19586: Large Villa with Pool Near Arezzo

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  • min $1,852/wk
  • max $5,110/wk
  • min $1,667/wk
  • max $4,599/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $511 when you book by Oct-20-2019**
5.0 stars
32 reviews
" We thoroughly enjoyed our stay. Alessandro couldn't have been nicer. He gave us directions to the local supermarkets and places of interest to visit...." - Robert
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Displaying 1 to 30 of 56 villas

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