Siena Guest Houses

We selected the 3506 homes worth renting in this location

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Adults

Age 13+

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Children

Age 1 to 12

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Home spotlights in Siena

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.

Escaping Time

Escaping Time

  • 7 guests

  • 3 bedrooms

Sovicille, Tuscany

Nestled in a sea of pea-green pastures, historic olive groves, and undulating hills, this home exudes Tuscan tranquillity. You'll find it in the little village of Brenna, just a forty-minute drive from Siena.

The Sweetest Life

The Sweetest Life

  • 32 guests

  • 16 bedrooms

Monteriggioni, Siena

Staying at this sprawling Tuscan estate is like having your own ancient borgo (small village). Hectares of grounds are dotted with cypress trees, dense woodland, ancient olive groves and gardens blossoming with flowers.

The Tuscan Muse

The Tuscan Muse

  • 14 guests

  • 7 bedrooms

Tregole, Tuscany

With majestic views across rolling hills and olive groves, this home makes it easy to enjoy the magic of Italy. Set within a working winery, you’ll be treated to an authentic taste of rural life along with all the essentials you could need to slow down and spend quality time together.


We selected the top 3% holiday homes in Siena Guest Houses

Explore the 3506 most perfect homes in our collection

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Most popular homes in Siena

A Rustic Reverie

A Rustic Reverie

  • 4 guests

  • 2 bedrooms

Sovicille, Tuscany

Tuscan Flow

Tuscan Flow

  • 4 guests

  • 2 bedrooms

Castelnuovo Berardenga, Siena

Super Tuscan

Super Tuscan

  • 14 guests

  • 7 bedrooms

Castelnuovo Berardenga, Siena

Tuscan Whisper

Tuscan Whisper

  • 2 guests

  • 1 bedrooms

Gaiole in Chianti, Siena

Dreaming of Chianti

Dreaming of Chianti

  • 6 guests

  • 3 bedrooms

Castellina in Chianti, Tuscany

Sunlight in Tuscany

Sunlight in Tuscany

  • 5 guests

  • 2 bedrooms

Siena, Tuscany

The Summer Harvest

The Summer Harvest

  • 14 guests

  • 7 bedrooms

Castelnuovo Berardenga, Siena

Tranquil Days

Tranquil Days

  • 6 guests

  • 3 bedrooms

Carpineta, Monteriggioni

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Frequently asked questions

Looking for guesthouse style accommodation in Siena, Tuscany, Italy? You've come to the right place: Our homes come fully furnished with well-equipped kitchens, toiletries in bathrooms & all linen included. Book today and enjoy a short or extended stay in the best guesthouse style accommodation that Siena, Tuscany, Italy has to offer. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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