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We selected the 1578 homes worth renting in this location

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Home spotlights in Montalcino

Tuscan Rose

Tuscan Rose

  • 10 guests

  • 3 bedrooms

Terranuova Bracciolini, Arezzo

Tucked away in vineyards and verdant pastures as far as the eye can see, this home promises tranquillity with breathtaking views to boot. You'll find it tucked away in Terranuova Bracciolini, surrounded by natural beauty and just a thirty-minute drive from Arezzo.

The Green Jewel

The Green Jewel

  • 8 guests

  • 4 bedrooms

Marsciano, Perugia

Wander through the gardens of this traditional Umbrian home and you’ll find yourself in a haven of natural tranquillity. From the wisteria-covered pergola and private pool to the multiple seating areas and perfectly positioned hammock, every detail has been considered to inspire total relaxation.

The Olive Stone

The Olive Stone

  • 6 guests

  • 3 bedrooms

Gaiole in Chianti, Siena

Enjoying a secluded spot in the Chianti countryside, this traditional stone villa is packed with things to keep you entertained. The gardens are a delight, where olive groves provide a spot for a shady stroll, and vineyards tumble down the hillside around you.

Lavender & Jasmine

Lavender & Jasmine

  • 20 guests

  • 9 bedrooms

Asciano, Siena

Tucked away amid gentle hills in the picturesque Val d’Orcia, this home is perfect for large groups. The traditional Tuscan villa and its annex have been elegantly restored, blending rustic charm with modern amenities like a professional kitchen.


We selected the top 3% holiday homes in Montalcino Villas

Explore the 1578 most perfect homes in our collection

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Most popular homes in Montalcino

Rusticana Retreat

Rusticana Retreat

  • 14 guests

  • 7 bedrooms

Castiglione d'Orcia, Siena

My Chianti Heart

My Chianti Heart

  • 12 guests

  • 4 bedrooms

Gaiole in Chianti, Siena

Journey to Beauty

Journey to Beauty

  • 18 guests

  • 9 bedrooms

Buonconvento, Siena

A Sweet Symphony

A Sweet Symphony

  • 4 guests

  • 2 bedrooms

La Dogana, Cortona

Vine & Blossom

Vine & Blossom

  • 8 guests

  • 4 bedrooms

Barberino Tavarnelle, Florence

Gold Rush

Gold Rush

  • 18 guests

  • 9 bedrooms

Buonconvento, Siena

Brunello Beauty

Brunello Beauty

  • 14 guests

  • 7 bedrooms

Montalcino, Siena

The Lucia

The Lucia

  • 10 guests

  • 5 bedrooms

Cortona, Arezzo

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Frequently asked questions

Secure a luxury stay in one of the remarkable Villas in our Montalcino, Siena, Tuscany, Italy collection. Our quality and consistency is unmatched, with only the top 3% of homes making it onto our site. Our meticulous home experts test everything from shower pressure to a home's feel and atmosphere, so there really is no need to worry about a thing. Your chosen home is also guaranteed to be fully furnished, with an excellently-equipped kitchen, essential bathroom toiletries, and linens all included. Acquire the help of our friendly experts, on standby 24/7 and always eager to assist you in your hunt for the finest luxury Villa in the entirety of Montalcino.

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