Book a stay in one of the best homes in Siena

We selected the 3416 homes worth renting in this location

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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

  • 1 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.

Antipasti on the Patio

Antipasti on the Patio

  • 14 guests

  • 6 bedrooms

Monteriggioni, Siena

Just 11km outside of Siena, nestled on a hilltop in the Tuscan countryside, you'll find this idyllic villa. It's a gorgeous spot with over a thousand square metres of grounds to explore, and plenty of space for your friends and family to roam.

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

Explore the 3416 most perfect homes in our collection

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Most popular homes in Siena

Tranquil Days

Tranquil Days

  • 6 guests

  • 3 bedrooms

Carpineta, Monteriggioni

Tuscan Haven

Tuscan Haven

  • 2 guests

  • 2 bedrooms

Sovicille, Tuscany

Lavender Tower

Lavender Tower

  • 22 guests

  • 11 bedrooms

Sovicille, Tuscany

Super Tuscan

Super Tuscan

  • 14 guests

  • 7 bedrooms

Castelnuovo Berardenga, Siena

Dreaming of Chianti

Dreaming of Chianti

  • 6 guests

  • 3 bedrooms

Castellina in Chianti, Tuscany

Breathe The Green

Breathe The Green

  • 8 guests

  • 4 bedrooms

Sovicille, Tuscany

Tuscan Flow

Tuscan Flow

  • 4 guests

  • 2 bedrooms

Castelnuovo Berardenga, Siena

Siena on My Mind

Siena on My Mind

  • 12 guests

  • 6 bedrooms

Sovicille, Tuscany

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