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The Best Coolstays in Italy
Published 15th January 2024
Is Italy the greatest holiday destination ever? It's got iconic landscapes, incredible culture, rich history and - best of all - fantastic, mouthwatering food.
Here are some of the most gorgeous Italian villas, apartments and glamping spots from which to enjoy it. Think sunbaked Tuscan farmhouses, cool and shady trulli and canal-front pied-a-terres in Venice. Che bella!
Live la dolce vita. See our full collection of Italian escapes. Coolstays in Italy
Terre di Bea
Cefalu - Sicily
Sleeps 5
Traditional Sicilian cottage with a pool and panoramic views out to sea, perfect for relaxing and romantic Mediterranean escapes.
Villa Toji
Bracciano - Roma
Sleeps 12
Striking villa set in large gardens in the Bracciano Hills, an hour north of Rome, perfect for a relaxing Italian holiday.
Capitolare Tower
Portovenere - Italy
Sleeps 2
Beautifully restored 12th century tower overlooking the sea on Italy’s Ligurian coast, perfect for a romantic escape.
Villa Itria
Locorotondo - Bari
Sleeps 6
Complete with private pool, gymnasium and covered terrace, this stunning three bedroom luxury villa in Puglia combines minimal design with traditional Italian flair.
Trullo San Michele
Ceglie Messapica - Puglia
Sleeps 6
Traditional and stunning Trullo with swimming pool and beautiful grounds, perfect for an Italian adventure in Puglia.
Palazzina Canal Apartment
Venice - Veneto
Sleeps 10
Grand five-bedroom Venetian apartment overlooking one of the main canals, perfect for families looking for an authentic taste of the city.
Lamia del Riccio
Ostuni (BR) - Apulia
Sleeps 6+2
Traditional Italian farmhouse in the Ostuni countryside with a pool and an outdoor kitchen, perfect for large families or group trips.
Chiesa del Carmine
La Bruna - Umbria
Sleeps 14
Lovingly restored 11th century church and 18th century farmhouse set in rich Umbrian countryside
Villa Heart
Massa Lubrense - Sorrento Coast
Sleeps 10
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
Casa Bea
Lipari - Sicily
Sleeps 13
Set on the Aeolian Island of Lipari, just north of Sicily, this stunning villa boasts a swimming pool and its own private access beach.
Diddy's Country
San Vito dei Normanni - Brindisi
Sleeps 15 adults + 2 babies
The ultimate family friendly getaway - An authentic, Italian farmhouse in rural Puglia that's just a short drive from the sea…
Villa Borgo Gerlino
Ambra - Tuscany
Sleeps 18+2
Enjoy the perfect lazy Tuscan holiday at this superb traditional villa with large pool and views for miles.
Palazzo Nianu
Neviano - Lecce
Sleeps 6
Beautifully restored palazzo in the heart of Neviano with roof garden, pool, BBQ, fire pit and pretty views of the village in Salento, Italy.
Ca’ Garzoni Moro -Salina
Venice - San Marco
Sleeps 6
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.
Villa Collombroso
Porano - Umbria
Sleeps 12
Escape to the Italian countryside in this stunning 400-year-old converted farmhouse perfect for large groups.
Novanta
Bibbiena - Tuscany
Sleeps 2 up to 50
Forage for truffles, learn Italian, make pasta or enjoy a picnic by the river before retiring to this gorgeous Tuscan holiday retreat.
Casa Talia
Modica - Sicily
Sleeps 2-5
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
Quattro Fontane
Roma - Rome
Sleeps 10
Live it up Italian-style at Quattro Fontane, a five-bed apartment hosting eleven guests in the depths of Rome, one of Europe's most historic cities.
Villa Montemaggio
Radda In Chianti - Tuscany
Sleeps 6
Ancient Tuscan cottage nestled in the heart of the Chianti district of central Italy, with outdoor swimming pool and views of the vineyards.
Airstreams Venice
Cavallino-Treporti - Venice
Sleeps 4
Iconic trailers with beautiful natural surroundings the perfect place to relax before heading out to explore the magical, enchanting city of Venice.
Casa San Gabriel
Pierantonio - Umbria
Sleeps Villas sleeping 2-4
Three rustic cool villas with jaw dropping views of Umbria - Perfect to explore Italy’s beautiful cultural soul.
Casa Mariavittori
Massa Lubrense - Sorrento Coast
Sleeps 5
Make this home in the hills with a view your base for trips to Sorrento, Pompeii and across the Amalfi Coast.
Villa Gaudia
Rignano Sullarno - Firenze
Sleeps 10
Relax in style at your luxury Italian villa in the heart of the rolling Tuscan hills with a hot tub, pool and incredible views.
Ursino Roof Garden Penthouse
Catania - Sicily
Sleeps 5
Contemporary penthouse just minutes from glorious sandy beaches in Catania, Sicily, with central location, perfect for couples or families.
Felder Alpin
Villanders - South Tyrol
Sleeps 6
Newly renovated, luxurious 11th-century farmhouse in South Tyrol with Finnish sauna and sweeping mountain views.
Cocotrullo
Ostuni - Italy
Sleeps 8
Unique artistic rural retreat in Ostuni with infinity pool, chromotherapy jacuzzi, a wonderful covered terrace and lots of luxury extras.
Attico Terrazza
Venice - Veneto
Sleeps 4
Live like a local at this beautiful open-planned terrace apartment, set right in the heart of Venice's bustling Castello district
Villa Lena
Palaia - Pisa
Sleeps 70
Hang out with the artists in residence on this spectacular Tuscan estate.