Book Luxury Holiday Rentals in Montalcino

Award-winning homes from £98

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Home spotlights in Montalcino

Artistic Retreat

Artistic Retreat

  • 8 guests

  • 4 bedrooms

Castiglione d'Orcia, Siena

Old collides with new at this secluded villa in the middle of the south Tuscan hills. Days can be spent hopping between the vineyards of the Val d’Orcia or day-tipping to the UNESCO village of Castiglione d'Orcia, a short drive away.

The Legendary Giulia

The Legendary Giulia

  • 8 guests

  • 4 bedrooms

Cellai, Rignano sull'Arno

Head into the Tuscan hills just outside the charming village of Cellai and keep an eye out for an imposing villa with its own bell tower. Almost unbelievably, this stunning property will be your home from home for however long you decide to stay.

The Rosso

The Rosso

  • 8 guests

  • 4 bedrooms

Radda in Chianti, Tuscany

Perched on the slopes of the Chianti hills, this stone villa effortlessly blends traditional Tuscan farmhouse charm with modern comforts. Since children under six aren’t permitted here, this villa is a perfect spot for a group seeking a retreat amongst sprawling gardens.

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 2220 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

Blue Umber

Blue Umber

  • 4 guests

  • 1 bedrooms

Seggiano, Grosseto

Bria

Bria

  • 6 guests

  • 3 bedrooms

Castel del Piano, Grosseto

Fairytale in Fresco

Fairytale in Fresco

  • 2 guests

  • 1 bedrooms

Certaldo, Florence

The Terracotta Sun

The Terracotta Sun

  • 6 guests

  • 4 bedrooms

Arezzo, Tuscany

The Maestro's Retreat

The Maestro's Retreat

  • 2 guests

  • 1 bedrooms

San Quirico d'Orcia, Siena

Brother Sun

Brother Sun

  • 6 guests

  • 3 bedrooms

Montalcino, Siena

Gold Rush

Gold Rush

  • 18 guests

  • 9 bedrooms

Buonconvento, Siena

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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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