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20 of the Best CoolStays in Italy

Published: 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

Trullo Sereno

Ostuni - Brindisi

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

Sleeps 7

From 214/night

Villa Fantese

Villa Fantese

Ostuni - Puglia

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

Sleeps 10

From 286/night

Contrada Fantese 1

Contrada Fantese 1

Ostuni - Puglia

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

Sleeps 6

From 214/night

Sigh

Sigh

Alessano - Puglia

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

Sleeps 3

From 106/night

Beach Villa

Beach Villa

Marina di Pulsano - Taranto

An exclusive, sea-front villa on Italys sun-kissed Puglia coastjust moments from the sparkling sea and a white sandy cove

Sleeps 12

From 198/night

Chiesa del Carmine

Chiesa del Carmine

La Bruna - Umbria

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

Sleeps 14

From 622/night

Mirror Houses

Mirror Houses

Bolzano - Italy

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

Sleeps 2+2 per house

From 168/night

Airstreams Rome

Airstreams Rome

Via Flaminia - Rome

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

Sleeps 4

From 92/night

La Dimora del Castelluccio

La Dimora del Castelluccio

Castiglione di Sicilia - Sicily

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

Sleeps 2-4 people

From 141/night

Casa Mariavittori

Casa Mariavittori

Massa Lubrense - Sorrento Coast

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

Sleeps 5

From 176/night

La Cuccagna

La Cuccagna

Gubbio - Perugia

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!

Sleeps 2-15

From 88/night

Villa Mori

Villa Mori

Lucca - Tuscany

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

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

From 1985/night

Vedetta Lodges

Vedetta Lodges

Scarlino - Tuscany

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.

Sleeps 2

From 66/night

La Collina del Sole

La Collina del Sole

Castelnuovo Di Garfagnana - Tuscany

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

Sleeps 10

From 308/night

Podere Palazzo

Podere Palazzo

Trevinano - Lazio

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

Sleeps 10 adults + 2 children

From 511/night

Poggio al Casone

Poggio al Casone

Crespina - Tuscany

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

Sleeps 2-6

From 106/night

Castello Di Postignano

Castello Di Postignano

Sellano - Perugia

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

Sleeps 28

From 140/night

Villa Chic

Villa Chic

Cortona - Arezzo

Two chic, designer villas in Italys rich Tuscan landscape, with private pools and stunning country vistas.

Sleeps 2-8

From 220/night

Villa Lena

Villa Lena

Palaia - Pisa

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

Sleeps 29

From 132/night

Podere Toscana

Podere Toscana

Volterra - Pisa

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

Sleeps 2-6 per property

From 85/night

Author:
Claire Wills
Claire is the International Editor for CoolStays. It's her mission to scout the globe for new amazing places to show you. You can follow her on Twitter, @clairelewills

New to CoolStays?

CoolStays showcases unique and unusual places to stay across the UK, Europe and worldwide. Accommodation includes glamping options such as gypsy caravans, shepherds huts, tipis, yurts, tents and cabins; luxury tree houses and cave houses; cool conversions such as planes, trains, boats, buses, churches, windmills, lighthouses and deluxe beach huts; as well as the coolest quintessential cottages, villas, B&Bs and boutique hotels.

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