Siena Luxury Homes

Award-winning homes from £98

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Home spotlights in Siena

A Glass of Brunello

A Glass of Brunello

  • 10 guests

  • 5 bedrooms

San Miniato, Pisa

This rural, pet-friendly villa offers equal amounts of elegance and tradition. Accessed through an electric gate and up an avenue of olive trees, you'll enjoy privacy and tranquillity on the outskirts of Siena.

Siena Charm

Siena Charm

  • 8 guests

  • 4 bedrooms

Siena, Tuscany

The quintessential Tuscan villa, this hillside four bedroom home looks out over the verdant Val d'Orcia. Ideal for families or friend groups seeking an authentic taste of Italian country life, the house sleeps eight and offers plenty of space for work, rest and play.

Sunset on the Landscape

Sunset on the Landscape

  • 8 guests

  • 4 bedrooms

Siena, Tuscany

Take a look at the amazing views of the Tuscan hills and Siena from this traditional home – they really do stop you in your tracks. The gardens are a dream as well – perfect for alfresco dining and drinks as the sun sets on the stunning landscape beyond.

The Tuscan Embrace

The Tuscan Embrace

  • 12 guests

  • 6 bedrooms

Siena, Tuscany

Nestled in the rolling Tuscan hills not far from Siena, this six-bedroom villa is packed with rustic character. The timber beams, exposed stonework, and other original features make staying here feel a little like stepping back in time – and we think that adds to the charm of the place.


We selected the top 3% holiday homes in Siena Homes

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Most popular homes in Siena

Antipasti on the Patio

Antipasti on the Patio

  • 14 guests

  • 6 bedrooms

Monteriggioni, Siena

Dreaming of Chianti

Dreaming of Chianti

  • 6 guests

  • 3 bedrooms

Castellina in Chianti, Tuscany

Chianti Sunrise

Chianti Sunrise

  • 4 guests

  • 2 bedrooms

Castelnuovo Berardenga, Siena

Tuscan Haven

Tuscan Haven

  • 2 guests

  • 2 bedrooms

Sovicille, Tuscany

Landscape Artist

Landscape Artist

  • 6 guests

  • 2 bedrooms

Monteroni d'Arbia, Siena

Super Tuscan

Super Tuscan

  • 14 guests

  • 7 bedrooms

Castelnuovo Berardenga, Siena

Terracotta & Vine

Terracotta & Vine

  • 6 guests

  • 3 bedrooms

San Sano, Gaiole in Chianti

Chianti Views

Chianti Views

  • 6 guests

  • 3 bedrooms

Castelnuovo Berardenga, Siena

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Frequently asked questions

All Plum Guide homes 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 home in Siena, Tuscany, Italy before approving it, so you can book with peace of mind.

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