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We found 44 CoolStays for you.Use the filters to narrow your selection.Ordered by: Recommended.
Gorgeous Tuscan Farmhouse with a sparkling infinity pool that offers stunning views of the Carrara Mountains whilst you swim
Three family-friendly apartments in Italy’s lush Umbrian landscape, packed with enchanting play areas for kids of all ages….
Two chic, designer villas in Italy’s rich Tuscan landscape, with private pools and stunning country vistas….
Uncover the mystery and romance of Italy’s lush Basilicata region at these rustic-luxe apartments with B&B option hidden amongst the hills…
A charming B&B and self catering cottage nestled on a pretty Umbrian hilltop, offering spectacular views of the countryside and an authentic Italian experience!
A truly tranquil Sicilian haven - Lounge around the pool, watch movies beneath the stars and explore the fabulous nearby beaches
Über stylish trullo with Eastern-influenced decor and lush gardens, perfect for a romantic and relaxing holiday.
Lovingly restored 11th century church and 18th century farmhouse set in rich Umbrian countryside
Three rustic cool villas with jaw dropping views of Umbria - Perfect to explore Italy’s beautiful cultural soul.
Beautiful rural views await at this restored country house in Italy’s lush Umbrian hills.
Delightful guesthouse overlooking the protected Ispica valley and necropolis of Calicantone, Casa al Castello is exclusive and fascinating.
Hang out with the artists in residence on this spectacular Tuscan estate.
Beautifully styled boutique hotel right on Venice’s grand canal – live an opulent Art Deco lifestyle within minutes of the sights
Overlooking the historic Sardinian village of Bitti, extra-special Su Lithu is a charming poolside retreat with fine local cuisine and captivating views
A stunning renovation of an 1850s Sardinian lighthouse, now offering boutique Mediterranean living on the island’s southern coast
Gorgeous triple-cone trullo in the heart of Puglia, Southern Italy – designer style, rustic character, true relaxation
A secluded 600 year old farmhouse that has been beautifully restored in the heart of the Umbrian countryside.
Beautiful 5-bedroom villa in the Perugian hills, with outdoor pool and stunning gardens – the perfect place to experience the wonder of rural Italy
A 16th century palazzo in the centre of Renaissance Florence, with three bohemian suites just moments from the Duomo…
A boutique bed & breakfast in the heart of rural Sardinia that captures the romance of a bygone era…
Take a step back and live for the moment at this boutique farm hotel in rural Tuscany….
A boutique Sicilian hotel on the dramatic Mt Etna slopes, with chic-rustic interiors and a rich, local heritage…
Stunning boutique apartments in a breathtaking Tuscan vineyard setting with wonderful views.
A quirky B&B in a medieval Umbrian village, where themed rooms look out over the majestic Italian landscapes…
A restored 13th-century monastery in breathtaking Umbria, now with 7 glorious apartments, a pool and more
Enjoy sea views from this stylish apartment in the centre of Sorrento, the perfect base for exploring the Amalfi Coast.
17th century mansion in the Italian Lakes, recently renovated to inject luxury and technology while maintaining all the period architectural details, with stunning results.
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.
A designer hotel in the centre of ancient Rome that blends its endless loves of the arts with an ageing grandeur…
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.
Explore flourishing Alpine landscapes or magical winter scenes at this Italian chalet in the majestic Dolomite hills…
A hillside rural retreat with a stunning pool in the Umbrian countryside in Italy.
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.
Tradition, exclusivity and an exquisite attention to detail and quality: everything you could ask for at Puglia's beautiful Paringa!
Tucked into the hills, on the borders of Lazio, Tuscany and Umbria, is where you'll find the lovely stone villa of Casale Cocca.
A magical Tuscan retreat - Four properties, from couples retreats through to a family villa - in the quiet seclusion of the hills above Florence.
Perfect Italian getaway - Relax by the pool admiring breathtaking views or visit nearby vineyards, picturesque medieval towns and stunning seaside spots.
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
Make this home in the hills with a view your base for trips to Sorrento, Pompeii and across the Amalfi Coast.
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
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
A gorgeous casa in Positano on the Amalfi coast with inspiring views of the sea and the rugged mountainous coastline
Palatial Italian villa perfect for large groups looking to escape to the Amalfi Coast
Stunning contemporary villa with an amazing infinity pool in a jaw dropping Sicilian setting complete with outdoor cinema.