Rent Luxury Self-Catering Apartments in Siena

We selected the 3590 homes worth renting in this location

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Home spotlights in Siena

The Summer Harvest

The Summer Harvest

  • 14 guests

  • 7 bedrooms

Castelnuovo Berardenga, Siena

Nestled among hills dotted with olive groves and vineyards, this villa makes a comfortable base for large groups and family gatherings. Inside, you'll find two sitting rooms, two kitchens, and an array of cosy bedrooms.

Landscape Artist

Landscape Artist

  • 6 guests

  • 2 bedrooms

Monteroni d'Arbia, Siena

In years gone by, this building in the countryside surrounding Siena was a farmhouse. Today, however, those paying a visit to the address will find a really rather dreamy Tuscan getaway.

Tuscan Flow

Tuscan Flow

  • 4 guests

  • 2 bedrooms

Castelnuovo Berardenga, Siena

Nestled in the heart of the Tuscan countryside, this charming cottage offers a tranquil retreat for families or small groups. Set on a resort, if you’re not enjoying the privacy of the cottage garden or hot tub, you can take a refreshing dip in the shared pool, just a short stroll away, or challenge your friends to a game on the tennis court.

Beneath The Autumnal Sun

Beneath The Autumnal Sun

  • 10 guests

  • 5 bedrooms

Castelnuovo Berardenga, Siena

Sitting proudly in the Chianti landscape, surrounded by woods, olive trees and row upon row of vines – this ancient farmhouse is the dream. It’s located in the prestigious setting of the Tolaini organic winery, one of the most esteemed in the area and produces delicious extra virgin olive oil and a fine selection of wines exported worldwide.


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

Explore the 3590 most perfect homes in our collection

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Most popular homes in Siena

Chianti Sunset

Chianti Sunset

  • 10 guests

  • 5 bedrooms

Radda in Chianti, Tuscany

Sun of Splendour

Sun of Splendour

  • 15 guests

  • 7 bedrooms

Fonterutoli, Castellina in Chianti

Toscana Per Sempre

Toscana Per Sempre

  • 2 guests

  • 1 bedrooms

Gaiole in Chianti, Siena

Tuscan Cypresses

Tuscan Cypresses

  • 10 guests

  • 7 bedrooms

Castelnuovo Berardenga, Siena

The Tuscan Farm

The Tuscan Farm

  • 14 guests

  • 7 bedrooms

Sovicille, Tuscany

Dreaming of Chianti

Dreaming of Chianti

  • 6 guests

  • 3 bedrooms

Castellina in Chianti, Tuscany

A Rustic Reverie

A Rustic Reverie

  • 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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