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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 51 villas
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Villa Dora - 21028: Villa on Large Estate Near San Gimignano

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  • min $5,300/wk
  • max $9,900/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 $1,881 when you book by Oct-31-2020**
5.0 stars
28 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 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-31-2020**
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 $3,662/wk
  • min $1,869/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 Oct-31-2020**
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 Sasso - 19586: Large Villa with Pool Near Arezzo

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  • min $2,126/wk
  • max $5,110/wk
  • min $1,913/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-31-2020**
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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La Solaia - 20434: Villa in Tuscany Near Certaldo and the Chianti Region

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  • min $1,888/wk
  • max $3,448/wk
  • min $1,699/wk
  • max $3,103/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $345 when you book by Oct-31-2020**
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 $4,093/wk
  • min $2,064/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 Oct-31-2020**
5.0 stars
131 reviews
" Wonderful all around!..." - Cinnamon
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Villa Fiorentina - 21756: Villa Rental near Florence with Pool and Fruit Orchard

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  • min $7,500/wk
  • max $16,875/wk
  • min $4,050/wk
  • max $15,188/wk
  • Min Stay: 7 days
Sleeps 8 to 10 people
  • 4 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $3,450 when you book by Oct-31-2020**
5.0 stars
2 reviews
" Fantastic. Beyond our expectations...." - Maggie
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Villa Volterra - 19438: Beautiful Italian Villa near Volterra for Large Group

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  • min $7,743/wk
  • max $11,762/wk
  • min $6,969/wk
  • max $10,586/wk
  • Min Stay: 7 days
Sleeps 20 people
  • 10 double bedrooms
  • 11 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,176 when you book by Oct-31-2020**
5.0 stars
7 reviews
" Excellent. It exceeded my expectations. ..." - Louis
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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-31-2020**
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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Casa del Mulino - 14852: Chianti Tuscany Villa Rental, Near Siena

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  • min $2,451/wk
  • max $5,321/wk
  • min $2,206/wk
  • max $4,789/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $532 when you book by Oct-31-2020**
5.0 stars
37 reviews
" Absolutely excellent. ..." - Kerby
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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-31-2020**
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 Carmen - 22562: Villa Rental in Tuscany, Montepulciano

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  • min $30,874/wk
  • max $48,516/wk
  • min $27,787/wk
  • max $43,664/wk
  • Min Stay: 4 days
Sleeps 24 people
  • 12 double bedrooms
  • 12 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
** Save up to $4,852 when you book by Oct-31-2020**
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Villa la Magnolia - 15050: Luxury Tuscany Villa Near Lucca and Walking Distance to a Small Village

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  • $21,994/wk
  • $19,795/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $2,199 when you book by Oct-31-2020**
5.0 stars
3 reviews
" The villa was spectacular, even better than the photos. The grounds and surrounding areas were beautiful. It has been recently renovated and the owner spared no ..." - Elyce
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Vittoria Estate - 21883: Large Resort Estate in Umbria Ideal for Large Groups

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  • min $15,822/wk
  • max $23,733/wk
  • min $14,240/wk
  • max $21,360/wk
  • Min Stay: 7 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-31-2020**
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Casa del Mulino with Guesthouse - 14847: Charming Villa with Pool in Tuscany

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  • min $2,801/wk
  • max $5,811/wk
  • min $2,521/wk
  • max $5,230/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $581 when you book by Oct-31-2020**
4.5 stars
24 reviews
" Very Good. A little too far from grocery store and Florence...." - Mary
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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 $3,039/wk
  • max $7,596/wk
  • min $2,735/wk
  • max $6,836/wk
  • Min Stay: 3 days
Sleeps 14 people
  • 7 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $760 when you book by Oct-31-2020**
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Villa Collina - 22204: 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 $4,915/wk
  • min $2,395/wk
  • max $4,424/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 $492 when you book by Oct-31-2020**
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Girasole - 20 - 21309: Villa with Pool and 2 Guesthouses for a Group in Eastern Tuscany

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  • min $8,439/wk
  • max $12,696/wk
  • min $7,595/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 $1,270 when you book by Oct-31-2020**
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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Casa Samuele - 8982: Large Villa Rental near Vorno, Lucca with Air Conditioning

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  • $12,759/wk
  • $11,483/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 $1,276 when you book by Oct-31-2020**
4.5 stars
5 reviews
" Pool area, kitchen, comfortable furnishings...." - Colleen
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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 $2,700/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 $496 when you book by Oct-31-2020**
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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Prima Casa - 19898: Chianti Villa near a Charming Village

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  • min $5,146/wk
  • max $9,557/wk
  • min $4,631/wk
  • max $8,601/wk
  • Min Stay: 3 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $956 when you book by Oct-31-2020**
5.0 stars
16 reviews
" Great experience in a spectacular villa...." - Viviane
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Villa Grandiosa - 20457: Private Villa on a Castle Estate near Certaldo

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  • min $9,102/wk
  • max $13,302/wk
  • min $8,192/wk
  • max $11,972/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,330 when you book by Oct-31-2020**
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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Villa Lucchesia - 20184: Historic 16th Century Villa in Tuscany with Private Pool and Shared Tennis Court

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  • min $7,070/wk
  • max $11,393/wk
  • min $6,363/wk
  • max $10,254/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
** Save up to $1,139 when you book by Oct-31-2020**
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 Filippo - 20058: Villa Near Cortona with a Private Pool

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  • min $3,080/wk
  • max $4,900/wk
  • min $2,772/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-31-2020**
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 Alessandro - 16485: Beautiful Hilltop Villa in Tuscany with Spectacular Views

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  • min $4,621/wk
  • max $11,464/wk
  • min $2,703/wk
  • max $10,318/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 $2,499 when you book by Oct-31-2020**
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 Senese - 20932: Luxury Villa Rental Near Siena

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  • Enquire for Rates
Sleeps 25 people
  • 3 single bedrooms
  • 11 double bedrooms
  • 14 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
5.0 stars
3 reviews
" The villa was lovely...." - Phyllis
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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 Oct-31-2020**
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 Oct-31-2020**
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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Poggio Antico - 15365: Villa Rental Chianti Tuscany Near Florence

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  • min $2,300/wk
  • max $4,554/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 Oct-31-2020**
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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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-31-2020**
5.0 stars
92 reviews
" Our stay was the highlight of our trip to Italy. ..." - Patty
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Displaying 1 to 30 of 51 villas

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