Siena Guest Houses

We selected the 3810 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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Infants

Under 1

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Pets

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Home spotlights in Siena

Super Tuscan

Super Tuscan

  • 14 guests

  • 7 bedrooms

Castelnuovo Berardenga, Siena

Whether you're swimming laps in the pool, lounging in bed or sipping a sundowner in the garden, this country home serves up breathtaking views from almost every angle. Surrounded by olive groves, world-famous vineyards and just a short drive from Siena, it’s a picture-perfect base for exploring the Chianti region.

A Rustic Reverie

A Rustic Reverie

  • 4 guests

  • 2 bedrooms

Sovicille, Tuscany

For a taste of authentic Tuscan living, this holiday home is a great choice. This apartment is one of six, renovated from a 15th-century structure by a historically conscious architect.

The Tuscan Farm

The Tuscan Farm

  • 14 guests

  • 7 bedrooms

Sovicille, Tuscany

Whether you’re here for the famous landscapes, rich history, culture or cuisine, one thing’s for sure, if you want to experience Tuscany at its finest, this charming villa is the place to be. In an idyllic countryside location, this home is surrounded by luscious greenery, rolling hills and landscapes, making it the ideal spot for sunset views and stargazing.

Gioia Pura

Gioia Pura

  • 6 guests

  • 3 bedrooms

Vitignano, Castelnuovo Berardenga

If you’re in search of picture-perfect Tuscan views, this apartment could be the one for you. It sits within a beautifully restored rural building and overlooks the chianti vineyards.


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

Explore the 3810 most perfect homes in our collection

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Most popular homes in Siena

Tuscany Magic

Tuscany Magic

  • 8 guests

  • 4 bedrooms

Castelnuovo Berardenga, Siena

Chianti Views

Chianti Views

  • 6 guests

  • 3 bedrooms

Castelnuovo Berardenga, Siena

Chianti Sunrise

Chianti Sunrise

  • 4 guests

  • 2 bedrooms

Castelnuovo Berardenga, Siena

Breathe The Green

Breathe The Green

  • 8 guests

  • 4 bedrooms

Sovicille, Tuscany

Chianti Sunset

Chianti Sunset

  • 10 guests

  • 5 bedrooms

Radda in Chianti, Tuscany

The Vine Vineyard

The Vine Vineyard

  • 18 guests

  • 11 bedrooms

Castelnuovo Berardenga, Siena

Toscana Per Sempre

Toscana Per Sempre

  • 2 guests

  • 1 bedrooms

Gaiole in Chianti, Siena

Terracotta & Vine

Terracotta & Vine

  • 6 guests

  • 3 bedrooms

San Sano, Gaiole in Chianti

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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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