Luxury Long Stay Rentals in Siena

We selected the best homes worth renting in this location

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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.

Rosemary & Olive

Rosemary & Olive

  • 2 guests

  • 1 bedrooms

Montalcino, Siena

For a taste of authentic Italian living, this stylish home opens its doors to the beauty of southern Siena. Located in the historic town of Montalcino (renowned for its Brunello wine), this is the perfect setting to experience the warmth and depth of Italian living.

A Midsummer Daydream

A Midsummer Daydream

  • 6 guests

  • 3 bedrooms

Barberino Tavarnelle, Florence

You might think that you have to pick between homes that respect tradition and those that embrace more contemporary design, but villas such as this one in the Florentine countryside show that you can have both if you choose wisely. Step behind the front door and you'll spot some of the rustic features common in the region's homes, be that wooden ceiling beams, stone archways or the large fireplace in the lounge.

Verdant Valley

Verdant Valley

  • 15 guests

  • 8 bedrooms

Poggibonsi, Siena

This elegant home in Tuscany is in a dreamy spot in a valley, in a countryside setting that leads to absolute relaxation. The villa is full of character, with antique furniture and wooden beams, in addition to mesmerising views.


We selected the top 3% holiday homes in Siena Long Stay Rentals

Explore the 1 most perfect homes in our collection

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Most popular homes

A Sweet Symphony

A Sweet Symphony

  • 4 guests

  • 2 bedrooms

La Dogana, Cortona

View From The Evening

View From The Evening

  • 4 guests

  • 2 bedrooms

Cortona, Arezzo

Tuscan Rose

Tuscan Rose

  • 10 guests

  • 3 bedrooms

Terranuova Bracciolini, Arezzo

The Legendary Giulia

The Legendary Giulia

  • 8 guests

  • 4 bedrooms

Cellai, Rignano sull'Arno

Soul of Lucca

Soul of Lucca

  • 4 guests

  • 2 bedrooms

Walled City, Lucca

A Rustic Reverie

A Rustic Reverie

  • 4 guests

  • 2 bedrooms

Sovicille, Tuscany

Aqua Olive

Aqua Olive

  • 8 guests

  • 4 bedrooms

Manciano, Grosseto

Sunflower Beams

Sunflower Beams

  • 3 guests

  • 2 bedrooms

Cortona, Arezzo

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Frequently asked questions

Explore our collection of luxury Extended Stay Rentals available for you to rent in Siena, Tuscany, Italy. Each and every home you'll find has been through a meticulous, multi-stage vetting process to ensure quality our guests can always count on. The Long Stay Rentals in our Siena, Tuscany, Italy collection come fully furnished with well-equipped kitchens, all linens, and essential bathroom toiletries included. And if you need any assistance, our friendly team of experts is always on hand to help plan your perfect stay.

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