Book Luxury Monthly Rentals in Cortona

We selected the 2168 homes worth renting in this location

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Home spotlights in Cortona

A Touch Of Ivy

A Touch Of Ivy

  • 7 guests

  • 3 bedrooms

Cortona, Arezzo

Like many traditional homes in Tuscany, this gorgeous old farmhouse is full of rustic elegance, with ivy and vines creeping over the exterior, beautifully matching it to its country surroundings. With traditional wooden floors boasting large woollen rugs and thick wooden beams on the ceilings, there’s no mistaking this home's authentic and historic character.

The Lucia

The Lucia

  • 10 guests

  • 5 bedrooms

Cortona, Arezzo

This quintessentially Italian home is nestled in the countryside just 5 kilometres from the beautiful town of Cortona. Days here can be spent hiking, cycling and exploring the historic hilltop towns of Tuscany.

A Tranquil Place

A Tranquil Place

  • 4 guests

  • 2 bedrooms

Cortona, Arezzo

Set in the foothills fringing the medieval town of Cortona and surrounded by olive and fir trees, the setting of this traditional cottage couldn't be more Tuscan if it tried. The interiors may be too rustic for some, but they would perfectly suit a small family or group of friends looking for a fuss-free stay.

A Triumph in Tuscany

A Triumph in Tuscany

  • 6 guests

  • 3 bedrooms

Cortona, Arezzo

This contemporary villa set on the edge of Terontola in southern Tuscany is just the ticket for those seeking a serene escape away from it all. Boasting modern interiors, a private pool and sun-kissed terraces, it’s a real gem.


We selected the top 3% holiday homes in Cortona Monthly Rentals

Explore the 2168 most perfect homes in our collection

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Most popular homes in Cortona

Garden Oasis Retreat

Garden Oasis Retreat

  • 2 guests

  • 1 bedrooms

Cortona, Arezzo

Tuscan Sunflower

Tuscan Sunflower

  • 8 guests

  • 4 bedrooms

Cortona, Arezzo

Vineyard Vistas

Vineyard Vistas

  • 6 guests

  • 3 bedrooms

Cortona, Arezzo

Il Sogno

Il Sogno

  • 4 guests

  • 2 bedrooms

Cortona, Arezzo

Wild Rosemary

Wild Rosemary

  • 10 guests

  • 5 bedrooms

Castiglion Fiorentino, Arezzo

Upon a Golden Dream

Upon a Golden Dream

  • 8 guests

  • 4 bedrooms

Cortona, Arezzo

Fresco Fantastico

Fresco Fantastico

  • 6 guests

  • 3 bedrooms

Cortona, Arezzo

View From The Evening

View From The Evening

  • 4 guests

  • 2 bedrooms

Cortona, Arezzo

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Frequently asked questions

Discover the ultimate collection of luxury Monthly Rentals in Cortona, Arezzo, Tuscany, Italy, and say goodbye to all your travel troubles. Here at Plum Guide, it is our promise that each and every home in our range is in the top 3% of homes in its location, so there is no doubting the consistent quality we are able to offer. Secure your extended or short stay today and enjoy the trip of a lifetime in your fully furnished home, with every property on our site including all linens, essential bathroom toiletries, and a perfectly-equipped kitchen. Our meticulous home critics test everything from Wifi speed to a home's design, so you really can trust our judgement. Rent your perfect Cortona Monthly Apartment today with the help of our team of experts, on standby 24/7 to assist you with absolutely anything.

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