Siena Guest Houses

We selected the best homes worth renting in this location

Home spotlights

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.

Italian Rose Retreat

Italian Rose Retreat

  • 12 guests

  • 6 bedrooms

Cortona, Arezzo

Surrounded by stunning countryside, this traditional Italian villa is ideal for a rustic family escape or a friendly reunion. Whether you’re perched on one of the balconies upstairs or sunning yourself in the garden, you’ll have sprawling vistas to enjoy.

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.

Wild Onion

Wild Onion

  • 4 guests

  • 2 bedrooms

Fonterutoli, Castellina in Chianti

This cosy apartment is located in the heart of historic Fonterutoli, surrounded by beautiful Tuscan countryside. Spend your time visiting local vineyards and wineries, or take a day-trip to Siena.


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

Explore the 1 most perfect homes in our collection

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Most popular homes

Lilies in the Pond

Lilies in the Pond

  • 6 guests

  • 3 bedrooms

Migliarino Pisano, Vecchiano

The Olive Book

The Olive Book

  • 6 guests

  • 3 bedrooms

Foiano della Chiana, Tuscany

Life in Sepia

Life in Sepia

  • 4 guests

  • 2 bedrooms

Casole d'Elsa, Siena

A Tuscan Soul

A Tuscan Soul

  • 4 guests

  • 3 bedrooms

San Gimignano, Siena

Tuscan Haven

Tuscan Haven

  • 2 guests

  • 2 bedrooms

Sovicille, Tuscany

A Country Garden

A Country Garden

  • 10 guests

  • 6 bedrooms

Montepulciano, Siena

The Painted Rose

The Painted Rose

  • 15 guests

  • 9 bedrooms

Monte Argentario, Tuscany

Pisan Memoir

Pisan Memoir

  • 6 guests

  • 3 bedrooms

Pisa, Tuscany

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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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