The Best Homes in Siena

Award-winning homes from £98

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

0

Pets

An extra fee may apply

0

Home spotlights in Siena

Chianti Breeze

Chianti Breeze

  • 10 guests

  • 5 bedrooms

Gaiole in Chianti, Siena

This 400-year-old luxury farmhouse sits in the Chianti hills between Florence and Siena. Up on a hilltop, the view over the forest-clad countryside is simply sublime, from secluded seating nooks around the garden and from the 12-person dining table on the patio.

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.

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.

Tuscan Delight

Tuscan Delight

  • 4 guests

  • 2 bedrooms

Castelnuovo Berardenga, Siena

Nestled on a hillside in Chianti with far-reaching views, this ground-floor apartment is part of a small resort. While it does lack natural light in some areas due to its history as a farm building, it’s comfortable and well-equipped for a restful retreat.


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

Explore the 3578 most perfect homes in our collection

View on map

Most popular homes in Siena

Chianti Views

Chianti Views

  • 6 guests

  • 3 bedrooms

Castelnuovo Berardenga, Siena

Tuscan Cypresses

Tuscan Cypresses

  • 10 guests

  • 7 bedrooms

Castelnuovo Berardenga, Siena

The Tuscan Muse

The Tuscan Muse

  • 14 guests

  • 7 bedrooms

Tregole, Tuscany

Land of Beauty

Land of Beauty

  • 12 guests

  • 6 bedrooms

Castelnuovo Berardenga, Siena

Antipasti on the Patio

Antipasti on the Patio

  • 14 guests

  • 6 bedrooms

Monteriggioni, Siena

Landscape Artist

Landscape Artist

  • 6 guests

  • 2 bedrooms

Monteroni d'Arbia, Siena

Tuscany Magic

Tuscany Magic

  • 8 guests

  • 4 bedrooms

Castelnuovo Berardenga, Siena

The Summer Harvest

The Summer Harvest

  • 14 guests

  • 7 bedrooms

Castelnuovo Berardenga, Siena

View all

Check upcoming rates & availability for Siena Best Homes


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.

Search Our Collection