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SienaTuscanyItaly

Discover our holiday villas in Siena

Siena stops you in your tracks. A medieval square, a cathedral, and a city that has held onto itself for centuries. Our curated luxury rentals place you at the heart of it, close to the city, yet entirely your own.

Villas with pool in Siena

Explore our Holiday Villas in Siena

Our luxury villas near Siena with private pool sit out in the surrounding countryside, scattered through Chianti and the hills that ring the city. Close enough to reach Siena for a long lunch and an afternoon in the Campo, far enough to spend the evening with nothing but the cicadas for company.

Our Villas for Rent in Siena

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Pet Friendly
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Camporempoli
10 Guests6 Bedrooms
  • Overflow pool with views across Chianti's hills
Starting fromPer night€563
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SienaTuscanyItaly
Campassole
10 Guests5 Bedrooms
  • Walk to Radda from your private Tuscan retreat
Starting fromPer night€1,529
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SienaTuscanyItaly
Fontanelle
16 Guests8 Bedrooms
  • Magazine-featured villa among Brunello vineyards
Starting fromPer night€1,350
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Family Friendly
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Pozza Di Volpaia
11 Guests6 Bedrooms
  • Wine estate villa with complimentary tours
Starting fromPer night€472
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A tailored stay for you

We’re here to make travel feel easy. From the first inquiry to the smallest detail, every stay is centred on what matters to you. The right home, the right services, and thoughtful care that make each journey feel personal.

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Handpicked Villas With Character

We only list the homes that speak to us. Gardens for long lunches, pools for lazy mornings, living rooms that invite lingering. Each home selected with intent.
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Travel Advisors Who Listen

Tell us your story. Whether it’s a birthday, a reunion, or a long-overdue escape, our advisors match you with the right home and take care of every detail.
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Local Knowledge, Unlocked

Our team lives where you travel. We know the rhythm of the seasons, the best tables in town, and the details that turn a good stay into a great one.
SienaTuscanyItaly

About Siena

Create lasting Memories in our Holiday Villas in Siena

Siena does not ease you in gently. You arrive, you climb, and suddenly you are standing in the Campo — one of the great medieval squares in Europe — and the city announces itself all at once. The striped marble of the cathedral, the towers visible from every street, the terracotta rooftops that seem to have been arranged rather than built. It is a city with a strong sense of its own identity, and that identity has been carefully kept. What you see today is not a reconstruction or a preservation project. It is simply Siena, more or less as it has always been.
Few places in Italy wear their past as naturally as Siena does. The Palio — the famous horse race held twice a year in the Campo — is not a tourist event that happens to involve locals. It is the other way around: a deeply felt civic ritual that the city organises for itself, and that visitors are welcome to witness. The seventeen contrade, or city districts, each with their own colours, traditions, and loyalties, divide the city in ways that still matter to the people who live here. Understanding even a little of this adds a layer to a visit that most cities simply cannot offer.
Our team has been active in this part of Tuscany since 1984. That means we know the properties inside and out, we know the families who own them, and we have a real feel for which villas are close to Siena while still offering a true countryside experience. If you’re unsure which villa near Siena is the best fit for you, just tell us what you have in mind and we’ll be happy to help you get started.
Siena is often visited as a day trip from Florence, which is understandable and also a shame. The city changes when the day visitors leave. Evenings in the Campo, with a glass of Chianti and the square gradually quietening, are among the better things Tuscany has to offer. Mornings are good too: the cathedral before the crowds, breakfast in a bar where the clientele is mostly local, streets that feel like they belong to the neighbourhood rather than the itinerary. If you are staying nearby, an evening in Siena should be part of the plan.
Collections

The Siena collections

Our Siena collections bring together homes made for connection and calm. Family villas with space to gather, places where pets are welcome. All chosen for the way they make time here feel well spent.

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Family Friendly

Family Friendly

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Pet friendly

Pet friendly

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Siena Highlights

Explore the city

Siena rewards those who stay long enough to see it on its own terms. A medieval cityscape that has remained largely unchanged for centuries, a civic culture that runs deeper than most visitors realise, and a square that is simply one of the finest in Europe. Discover what makes Siena one of Tuscany's most distinctive and enduring cities.

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Piazza del Campo

Piazza del Campo

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The Duomo

The Duomo

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The Palio

The Palio

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Palazzo Salimbeni

Palazzo Salimbeni

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Travel with us

We believe great trips begin with understanding what matters to you. Our team helps you find the right home, plan the details, and make the most of every moment. Because in the end, travel is about more than places — it’s about time well spent.

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Let's plan your escape

Tell us what you're dreaming of—we'll take care of the rest. Our Travel Advisors will handpick the perfect villas and experiences for your next unforgettable trip.