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Book Family Friendly Rentals in Cortona

We selected the 1966 homes worth renting in this location

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Home spotlights in Cortona

Gramophones & Gazebos

Gramophones & Gazebos

  • 15 guests

  • 6 bedrooms

Castiglion Fiorentino, Arezzo

Stand on the flower festooned balcony of this large, stone-built farmhouse in the rolling Tuscan countryside and just take a few moments. With idyllic views over the estate's olive grove to the forest-clad hills beyond, we're sure you'll feel inspired.

La Tranquillità

La Tranquillità

  • 8 guests

  • 4 bedrooms

Cortona, Arezzo

This quaint redbrick villa with its duck-egg-blue shutters and intoxicating gardens is an enchanting escape in the south of Tuscany. Bordered by thick, leylandii hedges, the hectare of grounds is a symphony of colour, with blooming flowers and lush Mediterranean verdure.

The Ancient Stone

The Ancient Stone

  • 11 guests

  • 5 bedrooms

Cortona, Arezzo

Perched on the hills overlooking the Val di Chiana, this beautiful home seamlessly blends rustic charm with elegant Tuscan style to create a truly unforgettable stay. Less than a fifteen–minute walk from the centre of Cortona, the owners have thoughtfully restored this traditional farmhouse into a welcoming space that exudes charm.

The Angelico

The Angelico

  • 12 guests

  • 6 bedrooms

Cortona, Arezzo

Travel can fill us with a sense of wonder, openness and possibility. And this elegant villa is the perfect setting to discover the timeless beauty of Tuscany.


We selected the top 3% holiday homes in Cortona Family Friendly Rentals

Explore the 1966 most perfect homes in our collection

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Most popular homes in Cortona

By and By

By and By

  • 10 guests

  • 5 bedrooms

Fratticciola, Cortona

Blossom & Shutter

Blossom & Shutter

  • 18 guests

  • 9 bedrooms

Cortona, Arezzo

Old Tuscan Farmhouse

Old Tuscan Farmhouse

  • 8 guests

  • 3 bedrooms

Castiglion Fiorentino, Arezzo

A Tranquil Place

A Tranquil Place

  • 4 guests

  • 2 bedrooms

Cortona, Arezzo

The Softest Crimson

The Softest Crimson

  • 8 guests

  • 4 bedrooms

Le Corchie, Cortona

Sunflowers

Sunflowers

  • 4 guests

  • 2 bedrooms

Cortona, Arezzo

Timeless in Tuscany

Timeless in Tuscany

  • 8 guests

  • 4 bedrooms

Cortona, Arezzo

A Triumph in Tuscany

A Triumph in Tuscany

  • 6 guests

  • 3 bedrooms

Cortona, Arezzo

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Frequently asked questions

Discover the ultimate collection of luxury Family Friendly Rentals in Cortona, Arezzo, Tuscany, Italy. Here at Plum Guide, we prioritise customer satisfaction over everything, which is why we are so meticulous in what we do. Every home in our collection has been put through a vigorous 150-step vetting process, so we promise consistent quality you can count on. Each rental also comes fully furnished will essential bathroom toiletries, an excellently-equipped kitchen, and all linen included. Rent Cortona Family Friendly Homes now and secure yourself a trip to remember for all the right reasons. And call on the help of our friendly team, on standby night and day to ensure that your decision process is made as straightforward as possible.

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