Italy

We found 50+ CoolStays
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  • Sleeps: 2-4 people
  • Bedrooms: 2
Multiple Units Available

"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"

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  • Sleeps: 4
  • Bedrooms: 1

"Iconic trailers with beautiful natural surroundings the perfect place to relax before heading out to explore the magical, enchanting city of Venice."

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  • Sleeps: 4
  • Bedrooms: 2

"Explore the city of venice on foot or on the water before relaxing in your decadent, comfortable, and stylish Venetian apartment."

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  • Sleeps: 4
  • Bedrooms: 1

"Gorgeous apartment in the heart of Venice with it’s own pretty roof terrace offering wonderful views of the city - the perfect spot for a morning coffee."

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  • Sleeps: 5
  • Bedrooms: 2

"Putting you centre-stage in beautiful Venice, this 3rd-floor apartment boasts canal views and stylish interiors " making the most glamorous of city breaks for up to five guests"

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  • Sleeps: 6
  • Bedrooms: 3

"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."

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  • Sleeps: 14
  • Bedrooms: 8

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

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  • Sleeps: 7
  • 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"

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  • Sleeps: 5
  • Bedrooms: 2

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

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  • Sleeps: 4
  • 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."

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  • Sleeps: 3
  • Bedrooms: 2

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

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  • Sleeps: 9
  • Bedrooms: 5

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

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  • Sleeps: 4
  • Bedrooms: 2

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

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  • Sleeps: 12
  • Bedrooms: 7

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

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

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

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  • Sleeps: 18
  • Bedrooms: 6

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

  • 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.

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

  • 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 4 rooms.

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

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

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

  • Boutique Hotel with 3 rooms.

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

  • Boutique Hotel with 18 rooms.

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

  • Boutique Hotel with 24 rooms.

"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."

  • Sleeps: 8
  • Bedrooms: 3

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

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  • Sleeps: 9
  • Bedrooms: 5

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

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  • Sleeps: 2 to 15
  • 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."

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  • Sleeps: 14
  • Bedrooms: 6
 (1 review)

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

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  • Sleeps: 2-4
  • Bedrooms: 6

"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: 5
  • Bedrooms: 2

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

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  • Sleeps: 2-4
  • Bedrooms: 2

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

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  • Boutique Hotel with 9 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 10 rooms.

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

  • Sleeps: 12
  • Bedrooms: 5

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

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  • Sleeps: 9
  • 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."

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  • Sleeps: 8
  • Bedrooms: 4

"Fabulous Italian villa with lovely pool, picturesque gardens and a rustic, yet modern and luxurious interior."

  • Sleeps: 8
  • Bedrooms: 4

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

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  • Sleeps: 12
  • Bedrooms: 6

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

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  • Sleeps: 29
  • Bedrooms: 15

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

  • Boutique Hotel with 6 rooms.

"Escape to the Italian countryside at this Puglian retreat with swimming pool, spa and seductive surroundings... Ocean views included"

  • Sleeps: 2-3 per room
  • Bedrooms: 5

"Charm and luxury combine at Tenuta Cammarana, an historic Italian country house with stunning views across the island of Sicily."

  • Sleeps: 28
  • Bedrooms: 2

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

  • Sleeps: 2-5
  • Bedrooms: 10

"Centred around a lush Mediterranean garden, the inspired rooms of Casa Talia enjoy the finest views of historic Modica " all within easy reach of the coast"

  • Sleeps: 10
  • Bedrooms: 4

"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: 6
  • Bedrooms: 2

"Peacefully located in a small coastal village, The Olive Tree is close to Cefalù, has room for six and is full of Sicilian style"

  • Boutique Hotel with 12 rooms.

"Charming and spectacular place to stay in the heart of the romantic and historic city of Florence."

  • Sleeps: 2-6 per property
  • Bedrooms: 1-2 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"

  • Boutique Hotel with 8 rooms.

"Masseria Alchimia - Spectacular views and access to some breathtaking Puglia countryside as well as the inspiring Adriatic Coast."

  • Sleeps: 10 adults + 2 children
  • Bedrooms: 5

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

Live Calendar
  • Sleeps: 6
  • Bedrooms: 3
 (1 review)

"Luxurious, romantic residence with private four-season pool, spa and wine cellar perched on cliff with a majestic view of a fertile Umbrian valley."

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