Rent Cortona Homes with Swimming Pools

We selected the 1626 homes worth renting in this location

Who's coming along?

Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

An extra fee may apply

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Home spotlights in Cortona

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.

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.

Tuscan Sunflower

Tuscan Sunflower

  • 8 guests

  • 4 bedrooms

Cortona, Arezzo

A few kilometres from Cortona, this old farmhouse makes a rustic retreat for families. With a private pool, sprawling gardens, and a panoramic terrace, you'll have plenty of time to enjoy the Tuscan sun.

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.


We selected the top 3% holiday homes in Cortona Homes with Swimming Pools

Explore the 1626 most perfect homes in our collection

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Most popular homes in Cortona

The Ancient Stone

The Ancient Stone

  • 11 guests

  • 5 bedrooms

Cortona, Arezzo

Fresh As a Vine

Fresh As a Vine

  • 11 guests

  • 6 bedrooms

Montecchio, Castiglion Fiorentino

Tuscany in Bloom

Tuscany in Bloom

  • 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 Valley of Angels

The Valley of Angels

  • 14 guests

  • 7 bedrooms

Cortona, Arezzo

Tuscany Soul

Tuscany Soul

  • 6 guests

  • 3 bedrooms

Cortona, Arezzo

Museum of Light

Museum of Light

  • 20 guests

  • 9 bedrooms

Ferretto, Castiglione del Lago

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Check upcoming rates & availability for Cortona Homes with Swimming Pools


Frequently asked questions

You've certainly come to the right place if you are hoping to find one of the finest Holiday Homes with Swimming Pools in Cortona, Arezzo, Tuscany, Italy. Our exclusive collection consists solely of homes that have passed our thorough 150-step vetting process with flying colours, so you can book with true peace of mind, knowing that everything from decibel levels in the bedroom to a room's intangible atmosphere has been tested and approved. We don't list a huge number of homes one our site, just the right ones. Each property in our collection comes fully furnished and ready to welcome you, with a fully-equipped kitchen, essential bathroom toiletries, and all linen included. Contact our dedicated team of experts to find the perfect luxury Cortona Home to Rent with a Swimming Pool today, and set up a holiday to remember.

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