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We selected the 1478 homes worth renting in this location

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Home spotlights in Cortona

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.

Now and Forever

Now and Forever

  • 18 guests

  • 9 bedrooms

Castiglion Fiorentino, Arezzo

A traditional Tuscan villa nestled in the pristine countryside just a thirty-five-minute drive from Arezzo, this home is every bit as magical as it looks. Steeped in history and packed with period features and antiques, it's a slice of old-world romance that's suitable for a large group holiday or a special celebration.

Tuscan Sunflower

Tuscan Sunflower

  • 8 guests

  • 4 bedrooms

Cortona, Arezzo

A few kilometres from Cortona, this old farmhouse makes a rustic retreat for families. With a private pool, sprawling gardens, and a panoramic terrace, you'll have plenty of time to enjoy the Tuscan sun.

Tuscany in Bloom

Tuscany in Bloom

  • 18 guests

  • 9 bedrooms

Cortona, Arezzo

Made for outdoor living and large family gatherings, this home is sure to jump high up on your wishlist. We love the space this home has, and with two apartments independent from the main villa, it’s perfect for extended families where two couples are seeking a bit of added privacy.


We selected the top 3% holiday homes in Cortona Villas

Explore the 1478 most perfect homes in our collection

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Most popular homes in Cortona

The Main Event

The Main Event

  • 10 guests

  • 5 bedrooms

Metelliano, Cortona

A Tranquil Place

A Tranquil Place

  • 4 guests

  • 2 bedrooms

Cortona, Arezzo

A Touch Of Ivy

A Touch Of Ivy

  • 7 guests

  • 3 bedrooms

Cortona, Arezzo

La Tranquillità

La Tranquillità

  • 8 guests

  • 4 bedrooms

Cortona, Arezzo

Old Tuscan Farmhouse

Old Tuscan Farmhouse

  • 8 guests

  • 3 bedrooms

Castiglion Fiorentino, Arezzo

Pietra House

Pietra House

  • 13 guests

  • 7 bedrooms

Camucia, Cortona

The Etruscan Lady

The Etruscan Lady

  • 17 guests

  • 8 bedrooms

Cortona, Arezzo

The Softest Crimson

The Softest Crimson

  • 8 guests

  • 4 bedrooms

Le Corchie, Cortona

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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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