Best Siena villas, inspected and handpicked for you

Your perfect holiday, in the perfect villa

Discover the beauty and comfort of our villas paired with excellent service. If any of the below resonates with you, you're in the perfect spot!

• Love comfort and convenience? Our curated villas in Tuscany, Puglia, the Amalfi Coast and around the country provide a luxurious haven for relaxation after your Italian adventures.
• Appreciate personalized service? From booking to departure, we offer expert local insights and customized assistance to ensure your stay is flawless.
• Planning a family holiday or a wedding? Whether it’s a family getaway or a special celebration, our concierge team takes the stress away and makes organising your trip effortless and enjoyable.
• Prefer a stress-free experience? With Villa Finder managing all the nitty-gritty, you can relax and focus on creating unforgettable memories in beautiful Italy.

Val d'Orcia, in southern Tuscany, is renowned for its iconic rolling hills, picturesque cypress trees, and rustic farmhouses. A UNESCO World Heritage site, it offers breathtaking views that have inspired countless artists and photographers. Explore historic towns like Pienza, famous for its Renaissance architecture, or Bagno Vignoni, known for its thermal baths dating back to Roman times.

Montalcino is a hilltop town surrounded by vineyards that produce Italy's renowned Brunello wine. Wine enthusiasts can visit prestigious wineries for tastings and tours and learn about the meticulous winemaking process that defines this region. The town is charming, with mediaeval walls and narrow streets lined with shops offering local specialities like pecorino cheese and artisanal goods.

Chianti Classico, located between Florence and Siena, is synonymous with the quintessential Tuscan landscape—rolling hills, vineyards, and olive groves. Villas here are close to picturesque villages like Greve in Chianti, where visitors can indulge in wine tastings at historic cellars or explore the weekly markets filled with fresh produce and local crafts. The region is also ideal for hiking and cycling enthusiasts.

San Gimignano is a UNESCO World Heritage site that transports visitors back in time. The town's well-preserved architecture and historic centre provide a glimpse into Tuscany's mediaeval past. Beyond its towers, San Gimignano offers charming squares, artisan workshops, and panoramic views from its ancient walls, making it a cultural gem amidst the Tuscan countryside.

Siena City immerses visitors in its rich history and vibrant culture. The city's historic centre, a UNESCO World Heritage site, features the magnificent Piazza del Campo, where the Palio horse race occurs annually. Visitors can explore the Gothic marvels of the Siena Cathedral (Duomo di Siena), with its intricate façade and stunning interior, or wander through narrow alleys lined with artisan shops and local trattorias.

Pienza is celebrated for its harmonious architecture and serene atmosphere. Designed by Pope Pius II as a model Renaissance town, Pienza boasts elegant palaces, beautiful churches, and panoramic viewpoints overlooking the Val d'Orcia. Visitors can savour Pecorino cheese, a local speciality, visit artisan workshops, or enjoy the town's peaceful ambience while strolling through its well-preserved streets.

Staying in a Siena villa offers families a unique blend of comfort, space, and cultural immersion. One of the primary reasons families choose villas is the ample space they provide. Unlike cramped hotel rooms, villas offer multiple bedrooms, spacious living areas, and often private gardens or pools where kids can roam freely. This space allows everyone to relax, unwind, and enjoy quality time together without feeling crowded.

Another critical advantage of villa stays is the home-like comfort they offer. Families can enjoy meals together at their own pace with fully-equipped kitchens, dining areas, and cosy living spaces. Whether preparing a hearty breakfast before exploring or winding down with a homemade dinner after sightseeing, the flexibility adds to the overall comfort and convenience.

For families who love outdoor activities, many villas in Siena boast expansive gardens or terraces where children can play safely while parents relax and soak in the Tuscan sunshine. These outdoor spaces also provide a perfect setting for family gatherings, whether it's a barbecue evening or simply enjoying a glass of local wine under the stars.

Cultural immersion is another highlight of staying in a Siena villa. Many villas are situated in or near historic towns or amidst picturesque vineyards, offering a genuine experience of local life and traditions. You can explore nearby attractions at your leisure, visit local markets, or participate in cultural events while enjoying the comfort and privacy of your villa retreat.

Moreover, staying in a villa can be cost-effective for families, especially larger groups. Villas often provide better value for money compared to booking multiple hotel rooms, as you pay for the entire villa rather than per person. This makes villas attractive for families looking to maximise their budget without compromising on comfort or amenities.

Whether you're seeking space, comfort, outdoor adventures, cultural experiences, flexibility in dining, or cost-effectiveness, staying in a Siena villa offers all these benefits and more, ensuring a memorable and enjoyable family vacation in the heart of Tuscany.

With Villa Finder, explore a curated collection of over 45 handpicked villas in Siena, each offering luxurious amenities and breathtaking views of the Tuscan landscape. Whether you're drawn to a modern villa with sleek interiors or a rustic farmhouse steeped in history, our diverse selection ensures a perfect retreat for every taste and occasion.

At Villa Finder, quality is paramount. Our handpicked selection extends across 4,000 villas globally, spanning Asia, Europe, and the Caribbean. Each property meets stringent criteria for comfort, style, and location, ensuring a memorable stay wherever you unwind.

Experience personalised service from start to finish with Villa Finder. Our dedicated location experts are here to tailor every aspect of your stay, from villa selection to additional services, ensuring your individual preferences are met with care and attention.

Say goodbye to hidden costs with Villa Finder. We offer transparent pricing with no extra fees, providing clarity and confidence in your booking process. Rest assured with our price match guarantee, ensuring you receive the best value for your luxury villa experience in Siena and beyond.

Choose Villa Finder for your next villa getaway and discover why discerning travellers trust us to deliver exceptional service and unforgettable stays worldwide.