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Italy

100+ CoolStays

  • Boutique Hotel with 4 suites rooms.
Multiple Units Available

"Four beautifully styled suites in a 19th Century Italian palace in the heart of Turin, perfect for romantic city breaks."

Live Calendar
  • Sleeps: 14
  • Bedrooms: 8

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

Live Calendar
  • 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: 16
  • Bedrooms: 8

"An architect-designed Tuscan villa that will take your breath away - with a private beach, 18 metre infinity pool and glorious views."

Live Calendar
  • Sleeps: 6+2
  • Bedrooms: 3

"Traditional Italian farmhouse in the Ostuni countryside with a pool and an outdoor kitchen, perfect for large families or group trips."

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  • Boutique Hotel with 8 rooms.

"Enjoy the quiet serenity of the countryside and sprawling views of the Piedmont hills in this luxury Italian villa."

  • Sleeps: 2-6
  • Bedrooms: 10

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

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  • 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"

  • 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: 13
  • Bedrooms: 6 in 4 suites

"Architecturally fascinating contemporary chalet lodge in the Dolomites with panoramic mountain views and mountain tranquility."

  • Sleeps: 4-6 per tent
  • Bedrooms: 2-3

"Delightful Italian glamping site situated in the Venetian Lagoon's countryside, surrounded by a XVII Century villa."

  • 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
  • Sleeps: 9
  • Bedrooms: 3

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

Live Calendar
  • 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: 2-4 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: 2
  • Bedrooms: 1

"Located in the countryside on the south east coastline of Tuscany, come and stay at BeVedetta Lodges and enjoy adults-only glamping that truly gives a 5-star experience."

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  • Sleeps: 25
  • Bedrooms: 12

"Gorgeous and giant villa in southern Italy with marvellous sea views, stylish design and pretty outdoor spaces."

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  • 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
  • Sleeps: 2-8
  • Bedrooms: 1-3 per property
 (1 review)

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

  • 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: 2-4
  • Bedrooms: 1

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

Live Calendar
  • 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: 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: 2-4
  • Bedrooms: 1

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

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."

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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"

Live Calendar
  • 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."

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  • 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: 21
  • Bedrooms: 8

"Beautiful country estate located in the heel of Italy with huge gardens, an infinity pool and accommodation options to suit any trip."

Live Calendar
  • Sleeps: 3
  • Bedrooms: 1

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

Live Calendar
  • Sleeps: 3
  • Bedrooms: 2

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

"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

"Stylish, spacious family apartment in the Dorso Duro area 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

"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: 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: 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: 19
  • Bedrooms: 7

"Hillside Tuscan Villa with luxury pool and breathtaking views offering a wonderful spot for a break in the sun"

  • 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
  • Sleeps: 14
  • Bedrooms: 6

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

Live Calendar
  • Sleeps: 18
  • Bedrooms: 8

"This incredible Tuscan villa has huge outdoor spaces, characterful interiors and great facilities - all minutes from Foiano della Chiana."

Live Calendar
  • Sleeps: 6
  • Bedrooms: 2

"Peacefully located in a small coastal village, The Olive Tree is close to Cefalu00f9, has room for six and is full of Sicilian style"

  • Sleeps: 12
  • Bedrooms: 5

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

Live Calendar
  • Sleeps: 5
  • Bedrooms: 2

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

  • Sleeps: 8
  • Bedrooms: 3

"Enjoy rolling rural views and a private pool at this gorgeous traditional Tuscan country house."

Live Calendar
  • Sleeps: 12
  • Bedrooms: 6

"History and luxury combine at Villa Cretole - a 200-year-old country house that has been renovated to the highest spec."

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: 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: 15
  • Bedrooms: 8

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

Live Calendar
  • 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: 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: 10+3
  • Bedrooms: 5

"This marvellous villa with gorgeous pool is situated in a beautiful part of Tuscany and offers relaxation and tranquility"

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"

  • Sleeps: 18
  • Bedrooms: 6

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

  • Sleeps: 18+2
  • Bedrooms: 9

"Enjoy the perfect lazy Tuscan holiday at this superb traditional villa with large pool and views for miles."

Live Calendar
  • Sleeps: 11
  • Bedrooms: 3

"Luxurious villa with pool overlooking the breathtaking Tuscan landscape offering a traditional and peaceful break for all the family."

  • 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
  • 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: 6
  • Bedrooms: 2

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

Live Calendar
  • Sleeps: 70
  • Bedrooms: 30

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

  • 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: 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
  • Boutique Hotel with 8 rooms.

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

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  • 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."

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  • Sleeps: 10
  • Bedrooms: 5

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

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  • 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."

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  • Sleeps: 2
  • Bedrooms: 1

"This comfy treehouse is a romantic retreat in the Piedmont countryside with offers spectacular views."

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: 30
  • Bedrooms: 9

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

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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."

  • Sleeps: 6
  • Bedrooms: 3

"A sophisticated, stylish apartment with a private terrace, within walking distance of the world-famous artistic and architectural treasures of Florence"

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  • Sleeps: 2-4 per studio
  • Bedrooms: 4

"Stay in one of these stunning apartments on offer at Riva Lofts - which sit in front of Florence's Cascine Park and Arno River."

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  • Sleeps: 10
  • Bedrooms: 5

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

Live Calendar
  • Sleeps: 8
  • Bedrooms: 4

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

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  • Sleeps: 16
  • Bedrooms: 8

"Castello Perugia in the Umbrian countryside has been luxuriously renovated and restored to provide the holiday of a lifetime."

Live Calendar
  • 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"

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  • Boutique Hotel with 6 rooms.

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

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  • Sleeps: 8
  • Bedrooms: 3

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

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  • 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."

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  • Boutique Hotel with 12 rooms.

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

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  • 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: 6

"A hillside rural retreat with a stunning pool in the Umbrian countryside in Italy."

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."

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  • Boutique Hotel with 8 rooms.

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

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  • 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"

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  • Boutique Hotel with 8 rooms.

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

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  • Boutique Hotel with 6 rooms.

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

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  • Boutique Hotel with 4 rooms.

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

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

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

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  • 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: 20
  • Bedrooms: 8

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

  • 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..."

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  • Boutique Hotel with 3 rooms.

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

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  • 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: 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: 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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