Luxury Holiday Villas in Siena
With its striking red-brick architecture and magnificent medieval square, booking a luxury holiday villa in Siena puts you at the absolute heart of classic Tuscany. It’s iconic Piazza del Campo plays host to the Siena Palio twice a year. It’s also home to the Duomo with its black-and-white-striped Gothic facade and the 102-metre-tall Torre del Mangia.
We have hand-selected a premium collection of luxury holiday villas and spacious apartments throughout the province of Siena. Whether you want a quiet farmhouse overlooking the olive groves or a larger luxury villa within easy driving distance of the region’s famous wine towns, our team is here to help you plan the perfect luxury Italian holiday.
These luxury Siena villas are all within the Siena province of Tuscany.
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Where to stay for your luxury holiday in Siena
The province of Siena is massive and covers some of the most famous landscapes in Italy. Depending on what you want to see on your luxury holiday to Siena, a few areas stand out.
The Chianti Hills (Chianti Senese)
Just north of the city, the landscape rises into the vineyard-covered hills of Chianti. Staying in a luxury holiday villa in villages like Castellina or Radda in Chianti gives you a wonderfully traditional base. It is the premier spot for wine lovers who want to spend their days touring historic cellars and enjoying long, unhurried lunches in sun-drenched squares, all while keeping Siena just a short drive away.
The Crete Senesi and Asciano
To the south and east of Siena lies the Crete Senesi, a unique landscape of grey clay hills, isolated oak trees, and stunning ridges. Staying in a luxury holiday villa near a village like Asciano gives you peace and quiet. The views here are spectacular, changing colour from deep green in the spring to rich golden-brown in the hot summer months.
The Val d’Orcia borderlands
Further south in the province lies the UNESCO-protected Val d’Orcia, home to famous hilltop towns such as Pienza and Montalcino. Choosing a luxury holiday villa in this area places you among the most photographed landscapes in Italy. It is a brilliant base for food enthusiasts who want to try local pecorino cheeses, sample world-famous Brunello wines, and explore quiet, fortified villages at a relaxed pace.
Premium amenities for a luxury holiday in Siena
Our Siena luxury villa collection is designed to make group travel easy, balancing shared fun with plenty of personal space.
Luxury villas in Siena with pools
After a morning spent walking the steep stone streets of Siena, returning to your own private swimming pool is the ultimate luxury. Our luxury holiday villas feature beautifully positioned pools set within large, private gardens. Properties like Villa Conti offer wide pool decks with incredible views over the surrounding hills, perfect for cooling off in the afternoon.
Pet-friendly luxury holiday villas in Siena
We believe a family holiday is better when everyone can come along, including your dogs. Many of our luxury holiday villas feature large, enclosed gardens and shaded terraces. A large majority of our luxury villas offer ample, safe, private outdoor space for your pets to explore while you enjoy an alfresco meal on the veranda.
Luxury holiday villas in Siena for large groups
If you are planning a trip with an extended family or a big group of friends, space and privacy are essential. Our portfolio includes luxury holiday villas and shared estates that offer independent living quarters or separate guest cottages, alongside large outdoor dining tables, allowing everyone to holiday together comfortably.
Things to do on a luxury holiday in Siena
The city of Siena itself is astonishingly beautiful. It centres on the Piazza del Campo, home to the 102-metre-tall Torre del Mangia, along with the striking black-and-white-striped Gothic facade of the Duomo. Arguably, it is the Siena Palio that the city is most well known for, though. The Palio takes place twice a year: once on 2 July, the Palio of Provenzano, and once on 16 August, when the city hosts the Palio of the Assumption.
As much as we love Siena itself, we’re big fans of rural living over city life. As a result, in our opinion, driving through the Siena countryside is pretty much a perfect way to spend a day in this part of Tuscany during a luxury holiday. As you explore, take the opportunity to stop in at a winery, park up in one of the Medieval villages or enjoy a wonderful passeggiata through this idyllic landscape.
And, of course, you can use a stay in one of our luxury holiday villas in Siena as a base to explore the rest of Tuscany too. Enjoy our guide to the top 60 things to do in Tuscany for added inspiration on what to see and do during your Tuscany villa holiday.
Frequently asked questions about booking a luxury holiday in Siena
What is the Palio di Siena, and can we watch it?
The Siena Palio takes place twice a year on 2 July – the Palio of Provenzano – and 16 August – the Palio of the Assumption. It is possible to watch the palio from the centre of the Piazza del Campo for free. But be warned: it does get incredibly busy, so you’ll need to arrive extremely early to have any chance of seeing the action! Much more comfortable seating is available around the perimeter of the piazza, but prices for these top spots vary. There is no official box office to purchase tickets, but our trusted partners in Tuscany can help you to secure a seat.
Is Siena a good base for exploring the rest of Tuscany?
Yes, Siena is an excellent base, particularly for exploring the southern half of Tuscany. Located near the Chianti, Val d’Orcia, and Crete Senesi regions, it’s perfectly situated to access Tuscany’s iconic hilltop towns and picture-postcard landscapes. Just an hour by car to Tuscany’s capital city – Florence – and a similar distance from Arezzo, it’s also within two hours of Pisa, allowing guests to also tick off the region’s major landmarks.
Can your team help us book wine tastings or private chefs?
We certainly can. In fact, we wholeheartedly recommend you enjoy a wine tasting or private chef experience during your luxury holiday in Siena. Our sommeliers will bring the region’s iconic wines to life, whilst our recommended chefs will treat you to a veritable Tuscan feast.
