Book Luxury Holiday Rentals in Montalcino

Award-winning homes from £98

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Home spotlights in Montalcino

The Olive House

The Olive House

  • 10 guests

  • 5 bedrooms

Murlo, Siena

This villa is a rural oasis just south of Siena in the peaceful countryside, surrounded by woodlands and hills with panoramic views of Montalcino and Monte Amiata. You're just 24km from the charming city, while the Tuscan coast and Florence are also just over an hour's drive away, making it the ideal destination for those wanting to explore the area.

A Rustic Reverie

A Rustic Reverie

  • 4 guests

  • 2 bedrooms

Sovicille, Tuscany

For a taste of authentic Tuscan living, this holiday home is a great choice. This apartment is one of six, renovated from a 15th-century structure by a historically conscious architect.

The Terracotta Sun

The Terracotta Sun

  • 6 guests

  • 4 bedrooms

Arezzo, Tuscany

Surrounded by olive groves and ancient woods, this traditional farmhouse welcomes you to an authentic stay in the heart of Tuscany. Located on Pomaio hill with sweeping views across the countryside, this is a wonderful setting to retreat into the heart of nature.

Green in Bloom

Green in Bloom

  • 10 guests

  • 5 bedrooms

Buonconvento, Siena

Boasting traditional Tuscan charm, this countryside villa welcomes up to ten guests, making it an excellent choice for a family or group of friends looking for a restful getaway. Inside, there’s plenty of space for the group to spread out, then come together for meals in the garden.


We selected the top 3% holiday homes in Montalcino Holiday Rentals

Explore the 2342 most perfect homes in our collection

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Most popular homes in Montalcino

Artistic Grapes

Artistic Grapes

  • 2 guests

  • 1 bedrooms

Montalcino, Siena

Casa Rosana

Casa Rosana

  • 4 guests

  • 2 bedrooms

Castiglione d'Orcia, Siena

Trip To Tuscany

Trip To Tuscany

  • 12 guests

  • 7 bedrooms

Castiglione d'Orcia, Siena

Little Hills

Little Hills

  • 14 guests

  • 7 bedrooms

Sarteano, Siena

Thermae

Thermae

  • 4 guests

  • 2 bedrooms

San Miniato, Pisa

Arches & Enclaves

Arches & Enclaves

  • 16 guests

  • 8 bedrooms

Buonconvento, Siena

Brother Sun

Brother Sun

  • 6 guests

  • 3 bedrooms

Montalcino, Siena

Blue Umber

Blue Umber

  • 4 guests

  • 1 bedrooms

Seggiano, Grosseto

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Montalcino, Siena, Tuscany, Italy. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that Montalcino, Siena, Tuscany, Italy has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.

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