Italy

We found 50+ CoolStays
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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: 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: 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: 2
  • Bedrooms: 1

"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: 2-5
  • 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: 14
  • Bedrooms: 8

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

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."

Live Calendar
  • 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."

Live Calendar
  • Sleeps: 3
  • Bedrooms: 2

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

Live Calendar
  • 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…"

Live Calendar
  • 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."

Live Calendar
  • Sleeps: 18
  • Bedrooms: 6

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

  • 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"

Live Calendar
  • 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"

  • Sleeps: 8
  • Bedrooms: 3

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

Live Calendar
  • 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."

  • Boutique Hotel with 4 rooms.

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

  • 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."

Live Calendar
  • Sleeps: 12
  • Bedrooms: 5

"The perfect coastal Italian getaway for large groups - relax in the infinity pool gazing at the heart stopping sea views."

Live Calendar
  • 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."

Live Calendar
  • 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: 2-8
  • Bedrooms: 1-3 per property

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

  • Sleeps: 4-5 per apartment
  • Bedrooms: 2 per apartment
Multiple Units Available

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

Live Calendar
  • 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"

  • Sleeps: 2-4
  • Bedrooms: 2

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

Live Calendar
  • 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"

Live Calendar
  • Sleeps: 28
  • Bedrooms: 2

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

  • 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."

Live Calendar
  • Sleeps: 6
  • Bedrooms: 2

"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"

Live Calendar
  • 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: 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: 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."

Live Calendar
  • Sleeps: 6
  • Bedrooms: 3

"An historic, characterful town villa with a private wine cellar, heated pool and hot tub with space to dine outside against a stunning backdrop."

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