20 of the Best CoolStays in Italy

20 of the Best CoolStays in Italy

14th January 2019

Italy is fantastic destination for lovers of history, art, food and wine. From the sun drenched beaches of Puglia to the lush hillsides of Tuscany, the dramatic Amalfi coastline, to the beautiful island of Sicily, we have a fantastic collection of accommodation for you to choose from. You can stay in boutique apartments set in a vineyard, airstreams near Rome, palatial villas, and even an entire hamlet.

Trullo Sereno

Ostuni - Brindisi

Sleeps 7

A traditionally styled stone trullo in beautiful gardens with pool and sun terrace – it’s all you could wish for in a luxury Italian villa

Villa Fantese

Ostuni - Puglia

Sleeps 10

A captivating trullo house set deep in the beautiful Istira Valley with pretty pool and lovely gardens

Contrada Fantese 1

Ostuni - Puglia

Sleeps 6

An exquisite trullo in the captivating Puglia region, right in the heart of the Itria Valley.


Alessano - Puglia

Sleeps 3

A rural masseria with a modern design concept, complete with a private terrace and heated plunge pool…

Beach Villa

Marina di Pulsano - Taranto

Sleeps 12

An exclusive, sea-front villa on Italy’s sun-kissed Puglia coast…just moments from the sparkling sea and a white sandy cove…

Chiesa del Carmine

La Bruna - Umbria

Sleeps 14

Lovingly restored 11th century church and 18th century farmhouse set in rich Umbrian countryside

Mirror Houses

Bolzano - Italy

Sleeps 2+2 per house

Two luxurious holiday homes with Modern, striking designs, swimming pool, and traditional Italian surroundings.

Airstreams Rome

Via Flaminia - Rome

Sleeps 4

After a day exploring Rome retire back to this peaceful campsite with great pool and stylish, luxurious Airstream trailers

La Dimora del Castelluccio

Castiglione di Sicilia - Sicily

Sleeps 2-4 people

Take in the best of Italy's culture and history while nestled in the foothills of the majestic Mount Etna at La Dimora del Castelluccio

Casa Mariavittori

Massa Lubrense - Sorrento Coast

Sleeps 5

Make this home in the hills with a view your base for trips to Sorrento, Pompeii and across the Amalfi Coast.

La Cuccagna

Gubbio - Perugia

Sleeps 2-15

A charming B&B and self catering cottage nestled on a pretty Umbrian hilltop, offering spectacular views of the countryside and an authentic Italian experience!

Villa Mori

Lucca - Tuscany

Sleeps 28 (12 in the villa + 16 in the Farmhouse)

Close to historic Lucca, beautiful Villa Mori is set amid the Tuscan countryside and includes a spa, wine cellar and pool.

Vedetta Lodges

Scarlino - Tuscany

Sleeps 2

Located in the countryside on the south east coastline of Tuscany, come and stay at Vedetta Lodges and enjoy glamping that truly gives a 5-star experience.

La Collina del Sole

Castelnuovo Di Garfagnana - Tuscany

Sleeps 10

Gorgeous Tuscan Farmhouse with a sparkling infinity pool that offers stunning views of the Carrara Mountains whilst you swim

Podere Palazzo

Trevinano - Lazio

Sleeps 10 adults + 2 children

Savour the delights of authentic, Italian life at this 18th century farmhouse in the Tuscan and Umbrian hillsides….

Poggio al Casone

Crespina - Tuscany

Sleeps 2-6

Stunning boutique apartments in a breathtaking Tuscan vineyard setting with wonderful views.

Castello Di Postignano

Sellano - Perugia

Sleeps 28

A unique and fantastical village in the Umbrian hills, given a new lease of life by visionary Italian architects.

Villa Chic

Cortona - Arezzo

Sleeps 2-8

Two chic, designer villas in Italy’s rich Tuscan landscape, with private pools and stunning country vistas….

Villa Lena

Palaia - Pisa

Sleeps 29

Hang out with the artists in residence on this spectacular Tuscan estate.

Podere Toscana

Volterra - Pisa

Sleeps 2-6 per property

Rustic boutique chic; Four gorgeous properties set in an Etruscan valley of outstanding natural beauty with breathtaking views over an iconic Tuscan landscape

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