Book Luxury Monthly Rentals in Cortona

We selected the 2320 homes worth renting in this location

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Home spotlights in Cortona

Wrapped in Jasmine & Aloe

Wrapped in Jasmine & Aloe

  • 12 guests

  • 6 bedrooms

Castiglion Fiorentino, Arezzo

Nestled quietly in the countryside, this beautiful home will enchant you from the moment you first set eyes on it. With views over the Val di Chiana and Cortona, this home has it all – stunning stonework, exposed beams, comfortable furnishings and rich gardens.

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.

Olive Tree Embrace

Olive Tree Embrace

  • 14 guests

  • 7 bedrooms

Tuoro sul Trasimeno, Perugia

This villa, surrounded by vineyards and verdant hills, is guaranteed to sweep you off your feet. Whether you're looking for a quiet escape where you can truly relax or a base for your adventures in the Italian countryside, it's the ideal place to settle in and call home.

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.


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

Explore the 2320 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

A Tranquil Place

A Tranquil Place

  • 4 guests

  • 2 bedrooms

Cortona, Arezzo

Vineyard Vistas

Vineyard Vistas

  • 6 guests

  • 3 bedrooms

Cortona, Arezzo

The Ancient Stone

The Ancient Stone

  • 11 guests

  • 5 bedrooms

Cortona, Arezzo

The Valley of Angels

The Valley of Angels

  • 14 guests

  • 7 bedrooms

Cortona, Arezzo

Upon a Golden Dream

Upon a Golden Dream

  • 8 guests

  • 4 bedrooms

Cortona, Arezzo

The Bello

The Bello

  • 4 guests

  • 2 bedrooms

Cortona, Arezzo

Noah's Son

Noah's Son

  • 2 guests

  • 1 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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