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We selected the 2084 homes worth renting in this location

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Home spotlights in Siena

Dreaming of Chianti

Dreaming of Chianti

  • 6 guests

  • 3 bedrooms

Castellina in Chianti, Tuscany

After a day touring world-class vineyards, this home is the perfect place to unwind with a glass of Chianti. Sure, there’s no air conditioning here, and the traditional interiors may not be to everyone’s taste, but there’s no denying the beauty of the outdoor space.

The Vine Song

The Vine Song

  • 8 guests

  • 4 bedrooms

Castelnuovo Berardenga, Siena

Accessible via an unpaved, cypress-lined road and perched on sloping, vineyard-covered hills, this stylish stone villa is Tuscany at its best. Whether you’re here for an intimate wedding or a big family holiday, the place will set your heart pounding.

The Tuscan Hills

The Tuscan Hills

  • 4 guests

  • 2 bedrooms

Gaiole in Chianti, Siena

Tucked away on the edge of San Regolo village, this is a perfect pad for two couples or a small family on an Italian stay. Sure, its traditional interiors may not be to everyone’s taste, but the outdoor space will be a popular spot with all.

Landscape Artist

Landscape Artist

  • 6 guests

  • 2 bedrooms

Monteroni d'Arbia, Siena

In years gone by, this building in the countryside surrounding Siena was a farmhouse. Today, however, those paying a visit to the address will find a really rather dreamy Tuscan getaway.


We selected the top 3% holiday homes in Siena Villas

Explore the 2084 most perfect homes in our collection

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Most popular homes in Siena

Chianti Sunrise

Chianti Sunrise

  • 4 guests

  • 2 bedrooms

Castelnuovo Berardenga, Siena

Tuscany on My Mind

Tuscany on My Mind

  • 10 guests

  • 5 bedrooms

Castelnuovo Berardenga, Siena

Sun of Splendour

Sun of Splendour

  • 15 guests

  • 7 bedrooms

Fonterutoli, Castellina in Chianti

The Olive House

The Olive House

  • 10 guests

  • 5 bedrooms

Murlo, Siena

A Tulip Moment

A Tulip Moment

  • 18 guests

  • 9 bedrooms

Monteroni d'Arbia, Siena

Chianti Views

Chianti Views

  • 6 guests

  • 3 bedrooms

Castelnuovo Berardenga, Siena

Tuscan Haven

Tuscan Haven

  • 2 guests

  • 2 bedrooms

Sovicille, Tuscany

A Rustic Reverie

A Rustic Reverie

  • 4 guests

  • 2 bedrooms

Sovicille, Tuscany

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Frequently asked questions

Secure a luxury stay in one of the remarkable Villas in our 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 Siena.

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