Rent Luxury Self-Catering Apartments in Siena

We selected the 3256 homes worth renting in this location

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Home spotlights in Siena

Tuscan Hills

Tuscan Hills

  • 4 guests

  • 2 bedrooms

Monte Sante Marie, Asciano

This hilltop haven is perfect for those looking for a quiet, calm and restful stay in Tuscany. The villa can be found thirteen minutes outside of Asciano, with its medieval centre, amid stunning rolling countryside that catches the eye from every angle.

Dreaming of Chianti

Dreaming of Chianti

  • 6 guests

  • 3 bedrooms

Castellina in Chianti, Tuscany

After a day touring world-class vineyards, this home is the perfect place to unwind with a glass of Chianti. Sure, there’s no air conditioning here, and the traditional interiors may not be to everyone’s taste, but there’s no denying the beauty of the outdoor space.

My Chianti Heart

My Chianti Heart

  • 12 guests

  • 4 bedrooms

Gaiole in Chianti, Siena

Surrounded by vineyards tumbling down hillsides and towering trees, this stone villa sits in the heart of the Chianti Hills. The beautiful village of Lecchi with its ancient castle is just a six-minute drive away if you’re not too busy discovering the family-run wineries and vineyards on your doorstep.

Chianti Sunrise

Chianti Sunrise

  • 4 guests

  • 2 bedrooms

Castelnuovo Berardenga, Siena

Nestled in a private estate overlooking the Chianti hills, this cottage sets the tone for a magical Italian stay. There’s a private terrace and outdoor seating for alfresco dining, while the rooms make it easy to switch off and unwind.


We selected the top 3% holiday homes in Siena Self-Catering Apartments

Explore the 3256 most perfect homes in our collection

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Most popular homes in Siena

Chianti Views

Chianti Views

  • 6 guests

  • 3 bedrooms

Castelnuovo Berardenga, Siena

The Tuscan Farm

The Tuscan Farm

  • 14 guests

  • 7 bedrooms

Sovicille, Tuscany

Tuscan Flower

Tuscan Flower

  • 12 guests

  • 6 bedrooms

Castelnuovo Berardenga, Siena

Gioia Pura

Gioia Pura

  • 6 guests

  • 3 bedrooms

Vitignano, Castelnuovo Berardenga

The Sweetest Life

The Sweetest Life

  • 32 guests

  • 16 bedrooms

Monteriggioni, Siena

Siena on My Mind

Siena on My Mind

  • 12 guests

  • 6 bedrooms

Sovicille, Tuscany

Bellissima Casa

Bellissima Casa

  • 4 guests

  • 2 bedrooms

Sovicille, Tuscany

Chianti Dream

Chianti Dream

  • 4 guests

  • 2 bedrooms

San Sano, Gaiole in Chianti

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Frequently asked questions

Book luxury Self-Catering Apartments in Siena, Tuscany, Italy, and enjoy a memorable stay for all the right reasons. We leave no stone unturned in our pursuit of the most remarkable homes, vetting everything from shower pressure to design aesthetic. Every home in our collection of luxury Siena Self-Catering Rentals comes fully furnished with a well-equipped kitchen, all linens, and essential bathroom toiletries included. And should you need any help in finding the perfect home, our friendly experts are always on hand to help.

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