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Pienza Luxury Rentals

We selected the 538 homes worth renting in this location

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Home spotlights in Pienza

The Masterpiece

The Masterpiece

  • 20 guests

  • 9 bedrooms

Trequanda, Siena

This incredible Tuscan villa dates back to the 1600s and has been lovingly transformed into an organic and eco-sustainable farm. The landscape surrounding this home is impressive too – especially from the panoramic pool – as it's situated in Val d'Orcia, a UNESCO World Heritage Site.

The Pienza

The Pienza

  • 10 guests

  • 5 bedrooms

Pienza, Siena

Offering panoramic valley views over the surrounding olive groves, this countryside spot invites guests to experience rural Tuscany at its finest. Just a short drive from Monticchiello, you'll have easy access to the town's shops and restaurants despite your countryside location.

Follow the Moment

Follow the Moment

  • 4 guests

  • 2 bedrooms

Gavorrano, Grosseto

Just a sort drive from the beach at Follonica, this home is ideally located for a laidback coastal getaway. You’ll also have access to a communal swimming pool with beautiful views across the neighbouring 18-hole golf course.

The Sweet Heart

The Sweet Heart

  • 2 guests

  • 1 bedrooms

Porto Santo Stefano, Tuscany

Perched on the edge of Monte Argentario, this adults-only retreat sets the tone for blissful Italian getaway. Occupying the first floor, the apartment boasts stunning views which you can admire from the large terrace.

We selected the top 3% holiday homes in Pienza Luxury Rentals

Explore the 538 most perfect homes in our collection

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Most popular homes in Pienza

The Tuscan Moon

The Tuscan Moon

  • 10 guests

  • 5 bedrooms

Castellina in Chianti, Tuscany

Italian Grove

Italian Grove

  • 14 guests

  • 7 bedrooms

San Casciano dei Bagni, Tuscany

The One Light

The One Light

  • 12 guests

  • 6 bedrooms

Montalcino, Siena

The Old Watermill

The Old Watermill

  • 14 guests

  • 7 bedrooms

Montepulciano, Siena

The Hilltop Dream

The Hilltop Dream

  • 12 guests

  • 6 bedrooms

Radda in Chianti, Tuscany

Trasimeno Treasure

Trasimeno Treasure

  • 6 guests

  • 3 bedrooms

Passignano sul Trasimeno, Perugia

Peaceful Love

Peaceful Love

  • 10 guests

  • 5 bedrooms

Bucine, Arezzo

Forever Light

Forever Light

  • 12 guests

  • 6 bedrooms

Valverde, Sarteano

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A handpicked selection of the best luxury homes in Pienza, Siena, Tuscany, Italy, as chosen by the experts who've visited and vetted thousands of the city's homes. Luxurious interiors, sumptuous bedrooms and prime city centre locations. Available for short and extended stays.

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