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We selected the 1404 homes worth renting in this location

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Home spotlights in Cortona

Upon a Golden Dream

Upon a Golden Dream

  • 8 guests

  • 4 bedrooms

Cortona, Arezzo

Whether you're splashing about in the private pool, admiring the Tuscan scenery from the patio or dining on Italian delicacies in the setting sun, this charming villa is the perfect place to call home. Inside, every room oozes traditional character – stone walls here, wooden-clad ceilings there – creating a cosy, comfortable sanctuary.

Gardenia Farmhouse

Gardenia Farmhouse

  • 14 guests

  • 7 bedrooms

Cortona, Arezzo

For a taste of authentic Tuscany, look no further than this former farmhouse, just a fifteen-minute drive from Cortona and less than an hour from Arezzo. The home includes two independent apartments, so it’s perfect for families staying together or those seeking more privacy.

Rosemary Breeze

Rosemary Breeze

  • 12 guests

  • 6 bedrooms

Cortona, Arezzo

In the folds of the hills, this home is all about those Tuscan sunsets. Catch the golden hour, as the sun dips below the forest-clad hills, from the terrace where curtains frame the view and dining by candlelight is a delight.

The Valley of Angels

The Valley of Angels

  • 14 guests

  • 7 bedrooms

Cortona, Arezzo

If you’re in search of a rustic getaway, this 18th-century home ticks all the right boxes. Surrounded by trees, the garden offers beautiful views, as well as a swimming pool (open seasonally), a barbecue and a wood-burning pizza oven.


We selected the top 3% holiday homes in Cortona Villas

Explore the 1404 most perfect homes in our collection

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Most popular homes in Cortona

A Sweet Symphony

A Sweet Symphony

  • 4 guests

  • 2 bedrooms

La Dogana, Cortona

Pietra House

Pietra House

  • 13 guests

  • 7 bedrooms

Camucia, Cortona

A Triumph in Tuscany

A Triumph in Tuscany

  • 6 guests

  • 3 bedrooms

Cortona, Arezzo

The Scent of Hydrangeas

The Scent of Hydrangeas

  • 12 guests

  • 6 bedrooms

Arezzo, Tuscany

La Tranquillità

La Tranquillità

  • 8 guests

  • 4 bedrooms

Cortona, Arezzo

By and By

By and By

  • 10 guests

  • 5 bedrooms

Fratticciola, Cortona

Il Sogno

Il Sogno

  • 4 guests

  • 2 bedrooms

Cortona, Arezzo

Museum of Light

Museum of Light

  • 20 guests

  • 9 bedrooms

Ferretto, Castiglione del Lago

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Frequently asked questions

Secure a luxury stay in one of the remarkable Villas in our Cortona, Arezzo, Tuscany, Italy collection. Our quality and consistency is unmatched, with only the top 3% of homes making it onto our site. Our meticulous home experts test everything from shower pressure to a home's feel and atmosphere, so there really is no need to worry about a thing. Your chosen home is also guaranteed to be fully furnished, with an excellently-equipped kitchen, essential bathroom toiletries, and linens all included. Acquire the help of our friendly experts, on standby 24/7 and always eager to assist you in your hunt for the finest luxury Villa in the entirety of Cortona.

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