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Italy

50+ CoolStays.

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  • Sleeps: 3
  • Bedrooms: 1

"Stunning high ceilinged apartment in the heart of Venice with exposed rafters and high-end amenities."

Live Calendar
  • Sleeps: 4
  • Bedrooms: 2

"Fabulous two bedroom apartment in Venice by Saint Mark’s square in private palazzo with courtyard, lobby and concierge service."

Live Calendar
  • Sleeps: 4 (+2)
  • Bedrooms: 2

"Stylish contemporary apartment in the heart of Venice for up to six guests with a concierge service."

Live Calendar
  • Sleeps: 2 (+2)
  • Bedrooms: 1

"Luxury Venice apartment in the Palazzo Molin with views over the private courtyard, a stone's throw from St Mark's square."

Live Calendar
  • Sleeps: 15 adults + 2 babies
  • Bedrooms: 7
Multiple Units Available

"The ultimate family friendly getaway - An authentic, Italian farmhouse in rural Puglia that's just a short drive from the sea…"

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"

Live Calendar
  • Sleeps: 10
  • Bedrooms: 5

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

Live Calendar
  • Sleeps: 6
  • Bedrooms: 3

"An exquisite trullo in the captivating Puglia region, right in the heart of the Itria Valley."

Live Calendar
  • 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."

Live Calendar
  • 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."

Live Calendar
  • Sleeps: 14
  • Bedrooms: 8

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

Live Calendar
  • 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."

Live Calendar
  • Sleeps: 5
  • Bedrooms: 2

"Stunning, comfy, and wonderfully rustic converted Italian apartment in the heart of Ortygia, the Syracusan gem."

  • Sleeps: 2-4 per room
  • Bedrooms: 6
Multiple Units Available

"Gorgeously renovated bed and breakfast in this 18th Century farmhouse in the Piedmont region of Italy."

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"

  • Boutique Hotel with 4 rooms.

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

  • 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."

  • 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 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!"

Live Calendar
  • 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: 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."

  • 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: 5
  • Bedrooms: 2

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

Live Calendar
  • 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: 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: 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: 12
  • Bedrooms: 6

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

Live Calendar
  • Sleeps: 29
  • Bedrooms: 15

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

  • Sleeps: 8
  • Bedrooms: 4

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

  • Sleeps: 10
  • Bedrooms: 5

"Stay under the stone cone roof of your own Puglian trulli… in beautiful gardens with a 12m pool, and moments from historic Locorotondo"

  • 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: 3
  • Bedrooms: 1

"A rural masseria with a modern design concept, complete with a private terrace and heated plunge pool…"

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: 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

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

Live Calendar
  • Sleeps: 12
  • Bedrooms: 6

"Enjoy the beautiful Italian island of Sicily at Villa La Luna, a six-bedroom property positioned right on the seafront in the popular resort of Fontane Bianche."

Live Calendar
50+ CoolStays. Please use the filters to narrow your search.
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