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We selected the 2794 homes worth renting in this location

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Home spotlights in Cortona

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.

Pietra House

Pietra House

  • 13 guests

  • 7 bedrooms

Camucia, Cortona

Found in the rolling Tuscan countryside, only minutes away from Cortona, this beautiful villa exemplifies the best of both worlds. Bask in the peace and tranquillity the secluded location of this home offers, but find a bit of hustle Arezzo, Perugia, or even Florence at the end of a road trip.

Blossom & Shutter

Blossom & Shutter

  • 18 guests

  • 9 bedrooms

Cortona, Arezzo

This 17th-century Tuscan villa boasts a large private pool, lovely views, and a private chapel on its expansive grounds. The interior is traditional and elegant, and perhaps won't be to everyone's taste.

Fresh As a Vine

Fresh As a Vine

  • 11 guests

  • 6 bedrooms

Montecchio, Castiglion Fiorentino

Overlooking the lush Chiana Valley, this former farmhouse boasts views you won’t be forgetting any time soon. There are plenty of spots to sit back and soak it all in, but the pergola’s one of our favourites, perched right next to the pool and offering plenty of room for dining alfresco.


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

Explore the 2794 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

Old Tuscan Farmhouse

Old Tuscan Farmhouse

  • 8 guests

  • 3 bedrooms

Castiglion Fiorentino, Arezzo

A Sweet Symphony

A Sweet Symphony

  • 4 guests

  • 2 bedrooms

La Dogana, Cortona

Tuscan Stone & Olive Trees

Tuscan Stone & Olive Trees

  • 2 guests

  • 1 bedrooms

Cortona, Arezzo

Secret Calm

Secret Calm

  • 12 guests

  • 6 bedrooms

Cortona, Arezzo

Il Sogno

Il Sogno

  • 4 guests

  • 2 bedrooms

Cortona, Arezzo

Fresco Fantastico

Fresco Fantastico

  • 6 guests

  • 3 bedrooms

Cortona, Arezzo

Sunflower Beams

Sunflower Beams

  • 3 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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