Book Luxury Villas in Montalcino

We selected the 1598 homes worth renting in this location

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Home spotlights in Montalcino

Emerald Hills

Emerald Hills

  • 10 guests

  • 5 bedrooms

Monticiano, Siena

Formerly an olive mill, this Tuscan villa combines rustic charm with modern design elements. Just outside the small hamlet of Iesa, the villa is nestled in the serene Tuscan hills, surrounded by verdant countryside.

The Main Event

The Main Event

  • 10 guests

  • 5 bedrooms

Metelliano, Cortona

Dating back to the 18th century, this home provides the perfect setting for a dreamy Tuscan retreat – one that’s filled with the majestic beauty of the Italian countryside. And from the moment of arrival, you’ll want to pause to admire the unique charm of this setting.

A Sweet Symphony

A Sweet Symphony

  • 4 guests

  • 2 bedrooms

La Dogana, Cortona

Set amidst the verdant greenery of the Tuscan countryside, this elegant home invites you to experience the timeless charm of Italian living. And from the moment of arrival, the atmospheric presence of the villa feels inspiring.

Brunello Beauty

Brunello Beauty

  • 14 guests

  • 7 bedrooms

Montalcino, Siena

This villa has space for the whole family to spread out and get comfortable. With a games room and a private pool, there's never a dull moment here – and that's not even counting the many terraces where alfresco dining will no doubt be on the cards.


We selected the top 3% holiday homes in Montalcino Villas

Explore the 1598 most perfect homes in our collection

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Most popular homes in Montalcino

Hilltop Aria

Hilltop Aria

  • 14 guests

  • 7 bedrooms

Buonconvento, Siena

Thermae

Thermae

  • 4 guests

  • 2 bedrooms

San Miniato, Pisa

Journey to Beauty

Journey to Beauty

  • 18 guests

  • 9 bedrooms

Buonconvento, Siena

Umbrian Bliss

Umbrian Bliss

  • 2 guests

  • 2 bedrooms

Perugia, Umbria

Casa di Siena

Casa di Siena

  • 4 guests

  • 2 bedrooms

Torrita di Siena, Siena

Valley of Heaven

Valley of Heaven

  • 8 guests

  • 4 bedrooms

Castiglione d'Orcia, Siena

Lavender & Jasmine

Lavender & Jasmine

  • 20 guests

  • 9 bedrooms

Asciano, Siena

Never a Frown

Never a Frown

  • 20 guests

  • 10 bedrooms

Monte Castello di Vibio, Perugia

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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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