The Best Coolstays in Italy

The Best Coolstays in Italy

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.


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.


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.

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