Top 20 CoolStays in Italy

Top 20 CoolStays in Italy

9th January 2020

Italy is a dream destination - think food, art, wine, glorious beaches, beautiful mountains and stunning cities. To inspire you, we've chosen 20 of our favourite Italian holiday properties - from gorgeous traditional farmhouses with huge pools, to incredible villas with their own private beaches, to ancient converted churches in olive groves. Find your sun-soaked dolce vita at one of these 20 amazing Italian holiday getaways.

Villa Fantese

Ostuni - Puglia

Sleeps 10

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

Lamia del Riccio

Ostuni (BR) - Apulia

Sleeps 6+2

Traditional Italian farmhouse in the Ostuni countryside with a pool and an outdoor kitchen, perfect for large families or group trips.

Villa Borgo Gerlino

Ambra - Tuscany

Sleeps 18+2

Enjoy the perfect lazy Tuscan holiday at this superb traditional villa with large pool and views for miles.


Porto Santo Stefano - Tuscany

Sleeps 16

An architect-designed Tuscan villa that will take your breath away - with a private beach, 18 metre infinity pool and glorious views.

Poggio al Casone

Crespina - Tuscany

Sleeps 2-6

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


Bibbiena - Tuscany

Sleeps 2 up to 50

Forage for truffles, learn Italian, make pasta or enjoy a picnic by the river before retiring to this gorgeous Tuscan holiday retreat.

Villa i Pinoni

Lucca - Tuscany

Sleeps 14

Majestic hillside Tuscan Villa with pool, private gardens, incredible views and stunning original architectural features.

BeVedetta Lodges

Scarlino - Tuscany

Sleeps 2

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

Villa San Savino

nr Perugia - Umbria

Sleeps 8

A spectacular 14th-century converted church on an ancient estate of woodland and olive groves in central Umbria

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….

Casa San Gabriel

Pierantonio - Umbria

Sleeps 2-4

Three rustic cool villas with jaw dropping views of Umbria - Perfect to explore Italy’s beautiful cultural soul.

Casale Cocca

Lazio - Central Italy

Sleeps 9

Tucked into the hills, on the borders of Lazio, Tuscany and Umbria, is where you'll find the lovely stone villa of Casale Cocca.

Chiesa del Carmine

La Bruna - Umbria

Sleeps 14

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

Odles Lodge

Brixen - Italy

Sleeps 13

Architecturally fascinating contemporary chalet lodge in the Dolomites with panoramic mountain views and mountain tranquility.

Glamping Canonici

San Marco - Venice

Sleeps 4-6 per tent

Decadent glamping tents in the grounds of a stunning house outside Venice, part of an exclusive high-end resort.

The Red House

Venice - Veneto

Sleeps 6

Live as the locals do at The Red House, an elegant apartment for up to six in central Venice. Its own terrace looks out on the street, where you can dine and chat until late

The Venetian Penthouse

Venice - Veneto

Sleeps 4

After a day out exploring the city, sit on your terrace with a glass of wine and watch the sun set behind the rooftops of Venice.

Airstreams Procida

Procida - Naples

Sleeps 2-4

Boutique Airstream glamping park on the unspoiled Neapolitan Procida Island

The Cliff

Mazzaforno - Cefalu

Sleeps 10

Get ready to fall in love with the wonders of northern Sicily from this stunning designer villa with ocean-facing terraces, perfect for al fresco living.

Casa Bellevue

Positano - Amalfi Coast

Sleeps 7

A gorgeous casa in Positano on the Amalfi coast with inspiring views of the sea and the rugged mountainous coastline

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