Rent Cortona Homes with Swimming Pools

We selected the 1656 homes worth renting in this location

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

0

Pets

An extra fee may apply

0

Home spotlights in Cortona

Fairytale in Cortona

Fairytale in Cortona

  • 8 guests

  • 3 bedrooms

Cortona, Arezzo

Nestled in the vibrant Tuscan landscape, surrounded by traditional beauty lies this home. Whether you're lounging by the private pool or going for a swim to stay active as the kids play in the garden, or you're getting some last-minute remote work done at the dining table, you'll find it easy to make the most of your holiday here.

Tuscan Garden

Tuscan Garden

  • 12 guests

  • 6 bedrooms

Castiglion Fiorentino, Arezzo

Tucked away in Val di Chiana in the heart of the Tuscan countryside, this home promises an escape from it all. Ideal for larger groups, the main villa sleeps eight guests across four bedrooms.

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.

Tuscany in Bloom

Tuscany in Bloom

  • 18 guests

  • 9 bedrooms

Cortona, Arezzo

Made for outdoor living and large family gatherings, this home is sure to jump high up on your wishlist. We love the space this home has, and with two apartments independent from the main villa, it’s perfect for extended families where two couples are seeking a bit of added privacy.


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

Explore the 1656 most perfect homes in our collection

View on map

Most popular homes in Cortona

Wrapped in Jasmine & Aloe

Wrapped in Jasmine & Aloe

  • 12 guests

  • 6 bedrooms

Castiglion Fiorentino, Arezzo

Museum of Light

Museum of Light

  • 20 guests

  • 9 bedrooms

Ferretto, Castiglione del Lago

The Etruscan Lady

The Etruscan Lady

  • 17 guests

  • 8 bedrooms

Cortona, Arezzo

Now and Forever

Now and Forever

  • 18 guests

  • 9 bedrooms

Castiglion Fiorentino, Arezzo

A Tranquil Place

A Tranquil Place

  • 4 guests

  • 2 bedrooms

Cortona, Arezzo

Pietra House

Pietra House

  • 13 guests

  • 7 bedrooms

Camucia, Cortona

The Main Event

The Main Event

  • 10 guests

  • 5 bedrooms

Metelliano, Cortona

Tuscan Shadows

Tuscan Shadows

  • 10 guests

  • 5 bedrooms

Castiglion Fiorentino, Arezzo

View all

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.

Search Our Collection