Book Luxury Monthly Rentals in Cortona

We selected the 2594 homes worth renting in this location

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Home spotlights in Cortona

Valley Vista Villa

Valley Vista Villa

  • 10 guests

  • 5 bedrooms

Cortona, Arezzo

Located just one mile from the hilltop town of Cortona, this Tuscan villa is made up of two apartments in one charming and traditional farmhouse. Both apartments have their own separate entrances, making this a great choice for large groups.

The Main Event

The Main Event

  • 10 guests

  • 5 bedrooms

Metelliano, Cortona

Dating back to the 18th century, this home provides the perfect setting for a dreamy Tuscan retreat – one that’s filled with the majestic beauty of the Italian countryside. And from the moment of arrival, you’ll want to pause to admire the unique charm of this setting.

The Softest Crimson

The Softest Crimson

  • 8 guests

  • 4 bedrooms

Le Corchie, Cortona

Built as a farm at the end of the 19th century, this rural home has oodles of charm and Tuscan character. We're swooning over the original terracotta-vaulted ceilings, the exposed cork beams and the huge fireplace, which is the perfect spot to snuggle up with a cup of tea on wintery nights.

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.


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

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Most popular homes in Cortona

Garden Oasis Retreat

Garden Oasis Retreat

  • 2 guests

  • 1 bedrooms

Cortona, Arezzo

Sweetness of Time

Sweetness of Time

  • 14 guests

  • 5 bedrooms

Cortona, Arezzo

The Etruscan Lady

The Etruscan Lady

  • 17 guests

  • 8 bedrooms

Cortona, Arezzo

By and By

By and By

  • 10 guests

  • 5 bedrooms

Fratticciola, Cortona

Vineyard Vistas

Vineyard Vistas

  • 6 guests

  • 3 bedrooms

Cortona, Arezzo

Museum of Light

Museum of Light

  • 20 guests

  • 9 bedrooms

Ferretto, Castiglione del Lago

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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