The Best Homes in Siena

Award-winning homes from £98

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Home spotlights in Siena

Chianti Sunset

Chianti Sunset

  • 10 guests

  • 5 bedrooms

Radda in Chianti, Tuscany

Nestled in the Chianti countryside between Siena and Florence, this home has serenity running through its core. Sat atop a hill, surrounded by olive groves and vineyards (the site is actually an active organic winery), it’s impossible not to relax here.

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.

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.

Siena on My Mind

Siena on My Mind

  • 12 guests

  • 6 bedrooms

Sovicille, Tuscany

Families will love this stone villa. Featuring a main house, a studio apartment, and a separate cottage, you'll have plenty of space to chill out together or enjoy some quiet time alone.


We selected the top 3% holiday homes in Siena Best Homes

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Most popular homes in Siena

Chianti Dream

Chianti Dream

  • 4 guests

  • 2 bedrooms

San Sano, Gaiole in Chianti

The Tuscan Hills

The Tuscan Hills

  • 4 guests

  • 2 bedrooms

Gaiole in Chianti, Siena

A Rustic Reverie

A Rustic Reverie

  • 4 guests

  • 2 bedrooms

Sovicille, Tuscany

Tuscan Flow

Tuscan Flow

  • 4 guests

  • 2 bedrooms

Castelnuovo Berardenga, Siena

The Tuscan Embrace

The Tuscan Embrace

  • 12 guests

  • 6 bedrooms

Siena, Tuscany

Chianti Chic

Chianti Chic

  • 6 guests

  • 3 bedrooms

Castelnuovo Berardenga, Siena

Tuscany Magic

Tuscany Magic

  • 8 guests

  • 4 bedrooms

Castelnuovo Berardenga, Siena

Chianti Glow

Chianti Glow

  • 10 guests

  • 5 bedrooms

Gaiole in Chianti, Siena

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Frequently asked questions

Searching for your dream home in Siena, Tuscany, Italy? You've come to the right place: we’re the official selection of the world’s best homes. Our collection of homes in Siena, Tuscany, Italy come fully furnished with well-equipped kitchens, toiletries in bathrooms & all linen included. We obsessively check each home for you, so you can book a short or extended stay with peace of mind.

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