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Top 20 CoolStays in Italy

Published: 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

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

Lamia del Riccio

Lamia del Riccio

Ostuni (BR) - Apulia

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

Sleeps 6+2

From 317/night

Villa Borgo Gerlino

Villa Borgo Gerlino

Ambra - Tuscany

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

Sleeps 18+2

From 1030/night

Favoloso

Favoloso

Porto Santo Stefano - Tuscany

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

Sleeps 16

From /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

Novanta

Novanta

Bibbiena - Tuscany

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

Sleeps 2 up to 50

From 22/night

Villa i Pinoni

Villa i Pinoni

Lucca - Tuscany

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

Sleeps 14

From 477/night

BeVedetta Lodges

BeVedetta Lodges

Scarlino - Tuscany

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.

Sleeps 2

From 132/night

Villa San Savino

Villa San Savino

nr Perugia - Umbria

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

Sleeps 8

From 499/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

Casa San Gabriel

Casa San Gabriel

Pierantonio - Umbria

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

Sleeps 2-4

From 62/night

Casale Cocca

Casale Cocca

Lazio - Central Italy

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

Sleeps 9

From 323/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 692/night

Odles Lodge

Odles Lodge

Brixen - Italy

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

Sleeps 13

From 167/night

Glamping Canonici

Glamping Canonici

San Marco - Venice

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

Sleeps 4-6 per tent

From 132/night

The Red House

The Red House

Venice - Veneto

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

Sleeps 6

From 220/night

The Venetian Penthouse

The Venetian Penthouse

Venice - Veneto

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.

Sleeps 4

From 282/night

Airstreams Procida

Airstreams Procida

Procida - Naples

Boutique Airstream glamping park on the unspoiled Neapolitan Procida Island

Sleeps 2-4

From 128/night

The Cliff

The Cliff

Mazzaforno - Cefalu

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.

Sleeps 10

From 502/night

Casa Bellevue

Casa Bellevue

Positano - Amalfi Coast

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

Sleeps 7

From 337/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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