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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 40 villas
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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 Nov-30-2021**
5.0 stars
17 reviews
" Our family enjoyed the villa so much they wished they had more time to just enjoy the villa and stay on the property. From check-in to check-out, everyone made us ..." - Mary
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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 $2,070/wk
  • max $4,099/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 Nov-30-2021**
5.0 stars
183 reviews
" We had a wonderful time. The house was beautiful and everything we expected. ..." - Theresa
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Villa Anita - 17233: Elegant countryside Tuscan villa with pool near historic town, restaurants, attractions.

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  • $7,701/wk
  • $6,931/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 $770 when you book by Nov-30-2021**
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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Podere della Fraternita - 17413: Tuscany Villa with Four Bedrooms all with En Suite Baths

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  • min $3,000/wk
  • max $5,301/wk
  • min $2,700/wk
  • max $4,771/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 $530 when you book by Nov-30-2021**
5.0 stars
52 reviews
" Had a wonderful experience Place was great..." - Paula
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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 $8,910/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $990 when you book by Nov-30-2021**
5.0 stars
38 reviews
" Fantastic - Sandro and Nelson were excellent hosts...." - Peggy
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Casa del Mulino - 14852: Chianti Tuscany Villa Rental, Near Siena

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  • min $3,221/wk
  • max $5,601/wk
  • min $2,899/wk
  • max $5,041/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 $560 when you book by Nov-30-2021**
5.0 stars
38 reviews
" We loved the location the restored mill was beautiful, the home decor (mostly antiques were interesting), the internet was highly variable and could have lived for..." - Thomas
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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 Nov-30-2021**
4.5 stars
6 reviews
" It was fantastic. ..." - Jessica
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Girasole - 20 - 21309: Villa with Pool and 2 Guesthouses for a Group in Eastern Tuscany

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  • min $9,277/wk
  • max $14,527/wk
  • min $8,349/wk
  • max $13,074/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 $1,453 when you book by Nov-30-2021**
5.0 stars
5 reviews
" Overall, we had a very nice experience. The property is beautiful, the villa and the rooms are beautiful and all in a very peaceful setting. The proximity to the b..." - Craig
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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 Nov-30-2021**
4.0 stars
2 reviews
" Lovely, relaxing stay with easy access to onsite property managers. ..." - Katie
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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 Nov-30-2021**
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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Villa Gialla - 14 - 19056: Beautiful Large Villa Close to Florence

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  • min $5,601/wk
  • max $8,215/wk
  • min $5,041/wk
  • max $7,393/wk
  • Min Stay: 5 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $822 when you book by Nov-30-2021**
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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Casa Samuele - 8982: Large Villa Rental near Vorno, Lucca with Air Conditioning

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  • $11,902/wk
  • $10,712/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 $1,190 when you book by Nov-30-2021**
4.5 stars
5 reviews
" Pool area, kitchen, comfortable furnishings...." - Colleen
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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 $3,579/wk
  • max $7,001/wk
  • min $3,221/wk
  • max $6,301/wk
  • Min Stay: 5 days
Sleeps 14 people
  • 7 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $700 when you book by Nov-30-2021**
4.0 stars
1 reviews
" The bedrooms were comfortable and furnished beautifully the pictures were accurate and the kitchen was workable. Pretty good location once we found it, would have ..." - Janet
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Villa Letizia - 21843: Private luxury villa near Florence with pool, tennis court, beautiful gardens, spectacular views.

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  • min $17,503/wk
  • max $38,505/wk
  • min $15,753/wk
  • max $34,655/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $3,851 when you book by Nov-30-2021**
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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 Nov-30-2021**
5.0 stars
92 reviews
" Our stay was the highlight of our trip to Italy. ..." - Patty
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Villa Volterra - 19438: Beautiful Italian Villa near Volterra for Large Group

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  • min $8,514/wk
  • max $12,938/wk
  • min $7,663/wk
  • max $11,644/wk
  • Min Stay: 7 days
Sleeps 20 people
  • 10 double bedrooms
  • 11 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,294 when you book by Nov-30-2021**
5.0 stars
7 reviews
" Excellent. It exceeded my expectations. ..." - Louis
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Il Pavone - 20376: Charming Cottage for Two Couples or Small Family Near Cortona

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  • min $2,380/wk
  • max $3,500/wk
  • min $2,142/wk
  • max $3,150/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $350 when you book by Nov-30-2021**
5.0 stars
6 reviews
" We had a wonderful experience at this villa. Great views and neighborhood...." - Kathy
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Casa del Mulino with Guesthouse - 14847: Charming Villa with Pool in Tuscany

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  • min $3,676/wk
  • max $6,161/wk
  • min $3,308/wk
  • max $5,545/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 $616 when you book by Nov-30-2021**
4.5 stars
24 reviews
" Very Good. A little too far from grocery store and Florence...." - Mary
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Villa Alessandro - 16485: Beautiful Hilltop Villa in Tuscany with Spectacular Views

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  • min $4,621/wk
  • max $11,762/wk
  • min $4,159/wk
  • max $10,586/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 $1,176 when you book by Nov-30-2021**
5.0 stars
32 reviews
" Great overall experience. Beautiful villa in a beautiful setting. Very peaceful ..." - Lee Anne
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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 Nov-30-2021**
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Villa Sasso - 19586: Large Villa with Pool Near Arezzo

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  • min $2,221/wk
  • max $5,604/wk
  • min $1,999/wk
  • max $5,044/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $560 when you book by Nov-30-2021**
5.0 stars
33 reviews
" Very lovely property and owner. ..." - Olga
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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 Nov-30-2021**
5.0 stars
16 reviews
" Great experience in a spectacular villa...." - Viviane
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Villa Filippo - 20058: Villa Near Cortona with a Private Pool

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  • min $3,150/wk
  • max $6,300/wk
  • min $2,835/wk
  • max $5,670/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 $630 when you book by Nov-30-2021**
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 Senese - 20932: Luxury Villa Rental Near Siena

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  • min $28,004/wk
  • max $31,504/wk
  • min $25,204/wk
  • max $28,354/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 $3,150 when you book by Nov-30-2021**
5.0 stars
3 reviews
" The villa was lovely...." - Phyllis
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Vecchio Borgo - Bella Vista - 15435: Vacation Rental Agritourism in Tuscany

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  • min $1,233/wk
  • max $1,471/wk
  • min $1,110/wk
  • max $1,324/wk
  • Min Stay: 4 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $147 when you book by Nov-30-2021**
5.0 stars
51 reviews
" Our stay greatly facilitated the overall enjoyment of our experience in Tuscany. It is centrally located, and provided easy access to all of the places we wanted ..." - William
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Villa Grandiosa - 20457: Private Villa on a Castle Estate near Certaldo

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  • min $9,102/wk
  • max $10,502/wk
  • min $8,192/wk
  • max $9,452/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,050 when you book by Nov-30-2021**
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 Brunello - 20520: Spacious and Beautiful Tuscany Villa Near Montalcino

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  • min $8,435/wk
  • max $13,895/wk
  • min $7,592/wk
  • max $12,506/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,390 when you book by Nov-30-2021**
4.5 stars
2 reviews
" Excellent. Tuscany is exceptionally beautiful in the winter, and with the sun shining almost every day, all in all it was a lovely week...." - Judith
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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 $1,401/wk
  • max $2,101/wk
  • min $1,261/wk
  • max $1,891/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $210 when you book by Nov-30-2021**
5.0 stars
87 reviews
" Great. Claudia and Rudi terrific ..." - Frank
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Villa Angelica - 21956: Gorgeous Toscana Villa with pools, private garden and views

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  • min $3,896/wk
  • max $6,923/wk
  • min $3,506/wk
  • max $6,231/wk
  • Min Stay: 7 days
Sleeps 10 to 12 people
  • 5 double bedrooms
  • 5 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $692 when you book by Nov-30-2021**
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Villa Andreina - 14 - 19058: Lovely Villa with Countryside Views of Tuscany

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  • $3,493/wk
  • $3,144/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $349 when you book by Nov-30-2021**
5.0 stars
14 reviews
" Perfect!..." - Michal
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Displaying 1 to 30 of 40 villas

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