Italy

We found 50+ CoolStays
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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
  • Bedrooms: 4

A secluded 600 year old farmhouse that has been beautifully restored in the heart of the Umbrian countryside.

Live Availability
  • Sleeps: 12
  • Bedrooms: 6

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

Live Availability
  • Sleeps: 2-4
  • Bedrooms: 2

Beautiful rural views await at this restored country house in Italy’s lush Umbrian hills.

Live Availability
  • Sleeps: 6
  • Bedrooms: 3

Perfect Italian getaway - Relax by the pool admiring breathtaking views or visit nearby vineyards, picturesque medieval towns and stunning seaside spots.

Live Availability
  • Sleeps: 14
  • Bedrooms: 6

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

  • Sleeps: 28
  • Bedrooms: 2

The 15th and 21st centuries meet in a modern apartment within a historic gothic palace. Explore Venice from a location in the heart of the city.

Live Availability
  • Sleeps: 6
  • Bedrooms: 3

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

Live Availability
  • Sleeps: 7
  • Bedrooms: 3

Stylish, spacious family apartment in the Dorso Duro area of Venice.

Live Availability
  • Sleeps: 5
  • Bedrooms: 2

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.

Live Availability
  • Sleeps: 4
  • Bedrooms: 2

Modern, stylish apartment inside a late Gothic palace in the heart of Venice.

Live Availability
  • Sleeps: 3
  • Bedrooms: 2

Relax with a glass of wine on your giant roof terrace and watch as the sun sets behind the rooftops of Venice.

Live Availability
  • Sleeps: 9
  • Bedrooms: 5

Compact Venetian apartment for couples or small groups, perfectly positioned in the heart of the magical city of Venice.

Live Availability
  • Sleeps: 4
  • Bedrooms: 2

A 16th century village fortress on a secluded, Tuscan hillside, with an exclusive, sun-kissed pool and views across the lush, Italian countryside…

Live Availability
  • Sleeps: 12
  • Bedrooms: 7

Uncover the mystery and romance of Italy’s lush Basilicata region at these rustic-luxe apartments with B&B option hidden amongst the hills…

Live Availability
  • Sleeps: 2-4 per apartment
  • Bedrooms: 1 per apartment

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

Live Availability
  • Sleeps: 28 (12 in the villa + 16 in the Farmhouse)
  • Bedrooms: 14

Featured in Architectural Digest, this Italian ski chalet in the Piedmontese Alps is a rare and beautiful thing.

  • Sleeps: 18
  • Bedrooms: 6

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

Live Availability
  • Sleeps: 10
  • Bedrooms: 5

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

Live Availability
  • Sleeps: 14
  • Bedrooms: 8

Delightful guesthouse overlooking the protected Ispica valley and necropolis of Calicantone, Casa al Castello is exclusive and fascinating.

  • Boutique Hotel with 6 rooms.

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

  • Sleeps: 29
  • Bedrooms: 15

Beautifully styled boutique hotel right on Venice’s grand canal " live an opulent Art Deco lifestyle within minutes of the sights

  • Boutique Hotel with 18 rooms.

Overlooking the historic Sardinian village of Bitti, extra-special Su Lithu is a charming poolside retreat with fine local cuisine and captivating views

  • Boutique Hotel with 18 rooms.

A stunning renovation of an 1850s Sardinian lighthouse, now offering boutique Mediterranean living on the island’s southern coast

  • Boutique Hotel with 6 rooms.

Gorgeous triple-cone trullo in the heart of Puglia, Southern Italy " designer style, rustic character, true relaxation

Live Availability
  • Sleeps: 9
  • Bedrooms: 3

Beautiful 5-bedroom villa in the Perugian hills, with outdoor pool and stunning gardens " the perfect place to experience the wonder of rural Italy

Live Availability
  • Sleeps: 12
  • Bedrooms: 5

A 16th century palazzo in the centre of Renaissance Florence, with three bohemian suites just moments from the Duomo…

  • Boutique Hotel with 3 rooms.

A boutique bed & breakfast in the heart of rural Sardinia that captures the romance of a bygone era…

  • Boutique Hotel with 4 rooms.

Take a step back and live for the moment at this boutique farm hotel in rural Tuscany….

  • Boutique Hotel with 8 rooms.

A boutique Sicilian hotel on the dramatic Mt Etna slopes, with chic-rustic interiors and a rich, local heritage…

  • Boutique Hotel with 8 rooms.

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

Live Availability
  • Sleeps: 2-6
  • Bedrooms: 10

A quirky B&B in a medieval Umbrian village, where themed rooms look out over the majestic Italian landscapes…

  • Sleeps: 20
  • Bedrooms: 8

A restored 13th-century monastery in breathtaking Umbria, now with 7 glorious apartments, a pool and more

  • Sleeps: 30
  • Bedrooms: 9

Enjoy sea views from this stylish apartment in the centre of Sorrento, the perfect base for exploring the Amalfi Coast.

Live Availability
  • Sleeps: 7
  • Bedrooms: 3

17th century mansion in the Italian Lakes, recently renovated to inject luxury and technology while maintaining all the period architectural details, with stunning results.

Live Availability
  • Sleeps: 8
  • Bedrooms: 4

Indulge in Italy! Stay at this large and luxurious villa for eight that comes with a huge garden with art installations, a swimming pool and space to eat and relax outdoors at the foot of the Euganean Hills.

Live Availability
  • Sleeps: 9
  • Bedrooms: 4

A designer hotel in the centre of ancient Rome that blends its endless loves of the arts with an ageing grandeur…

  • Boutique Hotel with 10 rooms.

Stylish in the city; these selection of rooms and apartments in central Rome have it all, including chic furniture, wide windows to let in all the light and huge, comfortable beds.

  • Boutique Hotel with 9 rooms.
Multiple Units Available

Three family-friendly apartments in Italy’s lush Umbrian landscape, packed with enchanting play areas for kids of all ages….

Live Availability
  • Sleeps: 4-5 per apartment
  • Bedrooms: 2 per apartment

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

  • Sleeps: 2-8
  • Bedrooms: 1-3 per property

Get ready to relax with a trip to this indulgent hotel with a spa, a pool and even a life coach...and all in the middle of the Italian countryside.

  • Boutique Hotel with 24 rooms.

Tradition, exclusivity and an exquisite attention to detail and quality: everything you could ask for at Puglia's beautiful Paringa!

Live Availability
  • Sleeps: 8
  • Bedrooms: 3

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

Live Availability
  • Sleeps: 9
  • Bedrooms: 5
Multiple Units Available

A magical Tuscan retreat - Four properties, from couples retreats through to a family villa - in the quiet seclusion of the hills above Florence.

Live Availability
  • Sleeps: 2 to 15
  • Bedrooms: 5

Truly unique and beautiful suites nestled in some of Italy’s most serene countryside - wander the vineyards, swim in the pool and enjoy some spectacular cuisine

  • Sleeps: 2-4
  • Bedrooms: 6

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

Live Availability
  • Sleeps: 5
  • Bedrooms: 2

Spectacular coastal views, private pool and access to some of Italy’s most sought after destinations - Relax and unwind in this stunning cutting edge villa

Live Availability
  • Sleeps: 12
  • Bedrooms: 6

Huge swimming pool, fabulous coastal views and a private beach mere moments away, relax an unwind at this spectacular traditional villa near Naples and Pompeii

Live Availability
  • Sleeps: 10
  • Bedrooms: 4

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

Live Availability
  • Sleeps: 7
  • Bedrooms: 3

Palatial Italian villa perfect for large groups looking to escape to the Amalfi Coast

Live Availability
  • Sleeps: 15
  • Bedrooms: 8
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