Siena Luxury Houses

Award-winning homes from £98

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Home spotlights in Siena

Sweet Tuscany

Sweet Tuscany

  • 2 guests

  • 1 bedrooms

Gaiole in Chianti, Siena

Tailor-made for two, this charming villa promises a tranquil escape in the Tuscan countryside. We love the character-packed interiors, where you’ll find everything needed to kick back and relax.

The Summer Harvest

The Summer Harvest

  • 14 guests

  • 7 bedrooms

Castelnuovo Berardenga, Siena

Nestled among hills dotted with olive groves and vineyards, this villa makes a comfortable base for large groups and family gatherings. Inside, you'll find two sitting rooms, two kitchens, and an array of cosy bedrooms.

Land of Beauty

Land of Beauty

  • 12 guests

  • 6 bedrooms

Castelnuovo Berardenga, Siena

Surrounded by olive and cypress trees, this home perfectly embodies the timeless charm of Tuscan living. Dating back to the 15th-century, it began its life as a monastery, transitioned into a farm and now exists as the ideal setting for an immersive Italian escape.

Chianti Sunrise

Chianti Sunrise

  • 4 guests

  • 2 bedrooms

Castelnuovo Berardenga, Siena

Nestled in a private estate overlooking the Chianti hills, this cottage sets the tone for a magical Italian stay. There’s a private terrace and outdoor seating for alfresco dining, while the rooms make it easy to switch off and unwind.


We selected the top 3% holiday homes in Siena Houses

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Most popular homes in Siena

Dreaming of Chianti

Dreaming of Chianti

  • 6 guests

  • 3 bedrooms

Castellina in Chianti, Tuscany

Tuscan Hills

Tuscan Hills

  • 4 guests

  • 2 bedrooms

Monte Sante Marie, Asciano

Vineyard Sunset

Vineyard Sunset

  • 6 guests

  • 3 bedrooms

Radda in Chianti, Tuscany

Tuscan Whisper

Tuscan Whisper

  • 2 guests

  • 1 bedrooms

Gaiole in Chianti, Siena

The Tuscan Farm

The Tuscan Farm

  • 14 guests

  • 7 bedrooms

Sovicille, Tuscany

Antipasti on the Patio

Antipasti on the Patio

  • 14 guests

  • 6 bedrooms

Monteriggioni, Siena

Being of Beauty

Being of Beauty

  • 18 guests

  • 9 bedrooms

Lilliano, Castellina in Chianti

Chianti Blush

Chianti Blush

  • 2 guests

  • 1 bedrooms

Gaiole in Chianti, Siena

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Frequently asked questions

All Plum Guide houses in Siena, Tuscany, Italy have been tested and approved by our team of independent home critics. These meticulous beings inspect everything –from the convenience of each house’s location right down to the art on the walls– so what you see really is what you get. Worried about thin curtains? Accessibility? Maybe wifi speed is your biggest concern? Rest assured, we obsessively check each house in Siena, Tuscany, Italy before approving it, so you can book with peace of mind.

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