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Italy

93 CoolStays.

  • Sleeps: 2-6
  • Bedrooms: 10

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

  • 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: 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: 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."

Live Calendar
  • Sleeps: 4
  • Bedrooms: 2

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

Live Calendar
  • 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: 5
  • Bedrooms: 2

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

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: 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"

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: 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
  • 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: 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: 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: 4 (+2)
  • Bedrooms: 2

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

Live Calendar
  • Sleeps: 30
  • Bedrooms: 9

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

  • Sleeps: 3
  • Bedrooms: 1

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

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: 12
  • Bedrooms: 6

"An exclusive, sea-front villa on Italy’s sun-kissed Puglia coast…just moments from the sparkling sea and a white sandy cove…"

Live Calendar
  • Boutique Hotel with 8 rooms.

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

  • 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"

  • 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
  • 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: 10
  • Bedrooms: 4

"Sublime Italian villa sat high up on the hill with heart-stopping coastal views and a fabulous private pool."

Live Calendar
  • Boutique Hotel with 6 rooms.

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

  • 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: 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: 6

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

Live Calendar
  • Sleeps: 7
  • Bedrooms: 3

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

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
  • Boutique Hotel with 6 rooms.

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

  • Sleeps: 4
  • Bedrooms: 1

"Nordisk and Venetian design combine to offer a relaxing, stylish place to stay on the outskirts of Venice."

Live Calendar
  • 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"

  • Boutique Hotel with 8 rooms.

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

  • Sleeps: 2+2 per house
  • Bedrooms: 1 per house

"Two luxurious holiday homes with Modern, striking designs, swimming pool, and traditional Italian surroundings."

  • Boutique Hotel with 7 rooms.

"Enjoy the beautiful Ragusa Ibla area in Italy at Sabbinirica, a luxury guest house set right in the centre of the old town."

  • Sleeps: 12
  • Bedrooms: 5

"Escape to the Italian countryside in this stunning 400-year-old converted farmhouse perfect for large groups."

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: 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."

Live Calendar
  • Sleeps: 20
  • Bedrooms: 8

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

  • Sleeps: 7
  • Bedrooms: 3

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

Live Calendar
  • 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
  • Sleeps: 12
  • Bedrooms: 6

"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 Calendar
  • Sleeps: 2-4
  • Bedrooms: 1

"Boutique Airstream glamping park on the unspoiled Neapolitan Procida Island"

Live Calendar
  • 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: 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
  • 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
  • Boutique Hotel with 12 rooms.

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

  • Boutique Hotel with 3 rooms.

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

  • 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: 10
  • Bedrooms: 5

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

  • 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"

  • 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 4 rooms.

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

  • 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 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: 14
  • Bedrooms: 6

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

Live Calendar
  • Sleeps: 10
  • Bedrooms: 4

"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 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
  • Bedrooms: 1

"High end tent accommodation on Procida, a hidden gem half an hour from Naples."

Live Calendar
  • Sleeps: 2 up to 50
  • Bedrooms: 15

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

Live Calendar
  • Boutique Hotel with 10 rooms.

"Italian rural charm meets luxury living at Wine Relais Feudi Del Pisciotto, a beautifully restored farm offering spectacular views across the surrounding vineyards."

  • 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: 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

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

  • 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: 28
  • Bedrooms: 2

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

  • 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"

  • 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
  • Sleeps: 5
  • Bedrooms: 2

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

  • Sleeps: 3
  • Bedrooms: 1

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

Live Calendar
  • 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: 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: 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
  • 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: 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
  • Sleeps: 15
  • Bedrooms: 8

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

Live Calendar
  • Sleeps: 6
  • Bedrooms: 3

"Experience life within the walls of an ancient castle villa, with beautiful gardens, pool and a summer house kitchen."

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…"

  • Sleeps: 4
  • Bedrooms: 1

"After a day exploring Rome retire back to this peaceful campsite with great pool and stylish, luxurious Airstream trailers"

  • Sleeps: 2-6 people
  • Bedrooms: 3
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
  • 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: 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: 4-6
  • Bedrooms: 2
Multiple Units Available

"A gorgeous, family friendly renovated farmhouse in Umbria - the green heart of Italy"

Live Calendar
  • Sleeps: 9
  • Bedrooms: 3

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

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: 8
  • Bedrooms: 3

"Spacious, luxury Puglian villa with pool, jacuzzi, chef and sea view to delight the senses"

  • Sleeps: 29
  • Bedrooms: 15

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

  • Sleeps: 6
  • Bedrooms: 3

"Luxury Italian villa with panoramic views - Sit by the pool and gaze down at the sea over olive trees and villages."

  • Sleeps: 6
  • Bedrooms: 2

"Stylish apartment in the heart of the charming Italian town of Orvieto with great access to Tuscany and Umbria."

Live Calendar
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