Book Luxury Holiday Rentals in Montalcino

Award-winning homes from £98

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Home spotlights in Montalcino

Trip To Tuscany

Trip To Tuscany

  • 12 guests

  • 7 bedrooms

Castiglione d'Orcia, Siena

This sprawling estate in Tuscany is the stuff that dreams are made of. Composed of the main farmhouse, two outbuildings, and a shared hall, along with plenty of outdoor space, it's perfect for large groups planning an escape to the Italian countryside.

Valley of Heaven

Valley of Heaven

  • 8 guests

  • 4 bedrooms

Castiglione d'Orcia, Siena

Fall in love with the timeless charm of Tuscany from this home perched on the hills of Val D’Orcia. Outside, days can be spent by the saltwater pool and lounging under ancient oak trees.

Tuscan Twilight

Tuscan Twilight

  • 2 guests

  • 1 bedrooms

Arcidosso, Grosseto

With views as far as the Mediterranean coast on a clear day, it’s not hard to see why this traditional, semi-detached villa made it into our collection. We love the invitation to outdoor living here – after all, how can you resist sunny alfresco meals on the private terrace, or soaking up the sun from in or beside the communal pool?

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 2344 most perfect homes in our collection

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Most popular homes in Montalcino

Rosemary & Olive

Rosemary & Olive

  • 2 guests

  • 1 bedrooms

Montalcino, Siena

Bria

Bria

  • 6 guests

  • 3 bedrooms

Castel del Piano, Grosseto

The Olive House

The Olive House

  • 10 guests

  • 5 bedrooms

Murlo, Siena

Cracked Black Pepper

Cracked Black Pepper

  • 3 guests

  • 1 bedrooms

Suvereto, Livorno

Charming Countryside Villa

Charming Countryside Villa

  • 15 guests

  • 8 bedrooms

Murlo, Siena

Arches & Enclaves

Arches & Enclaves

  • 16 guests

  • 8 bedrooms

Buonconvento, Siena

Brother Sun

Brother Sun

  • 6 guests

  • 3 bedrooms

Montalcino, Siena

Il Mugnaio

Il Mugnaio

  • 6 guests

  • 3 bedrooms

Castel del Piano, 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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