Coolstays Blog

Round-ups

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!

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.

Live la dolce vita. See our full collection of Italian escapes.
Coolstays in Italy

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.

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 Lena

Palaia - Pisa

Sleeps 70

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

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.

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

Villa Collombroso

Porano - Umbria

Sleeps 12

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

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

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.

Felder Alpin

Villanders - South Tyrol

Sleeps 6

Newly renovated, luxurious 11th-century farmhouse in South Tyrol with Finnish sauna and sweeping mountain views.

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.

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.

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.

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 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.

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.

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.

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.

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.

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.

Capitolare Tower

Portovenere - Italy

Sleeps 2

Beautifully restored 12th century tower overlooking the sea on Italy’s Ligurian coast, perfect for a romantic escape.

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.

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.

Chiesa del Carmine

La Bruna - Umbria

Sleeps 14

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

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.

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.

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.

Type a location to get started

Coolstays Blog

Round-ups