ROUND-UPS
24 Gorgeous Italian Escapes
Published 9th March 2022
Just picture yourself by the pool with sunglasses and a cold negroni, living la dolce vita at one of these gorgeous Italian getaways. We've chosen some of our favourite stays - sun drenched Tuscan villas, stylish masserias with good food and even better wine and chic city apartments with beautiful rooftop views. Ciao bella.
See our full collection of Coolstays in Italy.Italian Coolstays
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.
Giarvino - Exclusive B&B
Acqui Terme - Piedmont
Sleeps 1-3 per room
Enjoy the quiet serenity of the countryside and sprawling views of the Piedmont hills in this luxury Italian villa.
Villa Capanne
San Giovanni del Pantano - Umbria
Sleeps 12
A secluded 600 year old farmhouse that has been beautifully restored in the heart of the Umbrian countryside.
LOOK TO Suite & Breakfast
Torino - Italy
Sleeps 2-3 per suite
Four beautifully styled suites in a 19th Century Italian palace in the heart of Turin, perfect for romantic city breaks.
Poggio al Casone
Crespina - Tuscany
Sleeps 2-6
Stunning boutique apartments in a breathtaking Tuscan vineyard setting with wonderful views.
Ventinove
Spoleto - Perugia
Sleeps 8
Beautiful villa set in the hills of central Italy, with a large swimming pool, olive grove and spectacular views.
Villa Roncovisi
Monsummano Terme - Tuscany
Sleeps 19
Hillside Tuscan Villa with luxury pool and breathtaking views offering a wonderful spot for a break in the sun
Masseria Moroseta
Ostuni - Puglia
Sleeps 2-14
Escape to the Italian countryside at this Puglian retreat with swimming pool, spa and seductive surroundings... Ocean views included
Villa Paola
Tropea - Italia
Sleeps 25
Gorgeous and giant villa in southern Italy with marvellous sea views, stylish design and pretty outdoor spaces.
Masseria Don Salvatore
Ostuni - Brindisi
Sleeps 6 +2
Olive grove views from the private pool at this stunning Southern Italian Villa.
Masseria Mongio
Otrand - Puglia
Sleeps 1-4 per suite
By the crystal clear waters of Baia dei Turchi in the Southern Italy's Salento is the beautiful and relaxing Masseria Mongio.
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.
Trullo Fico
Ostuni - Puglia
Sleeps 9
Gorgeous triple-cone trullo in the heart of Puglia, Southern Italy - designer style, rustic character, true relaxation
Villa dell'Angelo
Monsummano Terme - Tuscany
Sleeps 11
Luxurious villa with pool overlooking the breathtaking Tuscan landscape offering a traditional and peaceful break for all the family.
Casa San Gabriel
Pierantonio - Umbria
Sleeps 2-4
Three rustic cool villas with jaw dropping views of Umbria - Perfect to explore Italy’s beautiful cultural soul.
Chiesa del Carmine
La Bruna - Umbria
Sleeps 14
Lovingly restored 11th century church and 18th century farmhouse set in rich Umbrian countryside
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.
Villa Carrisi Salento
Parabita - Puglia
Sleeps 6
Three bedroom villa in the heart of rural Puglia, with a pool, two acres of orchards, and optional bespoke experiences
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.
Langhe Country House
Neive - Piedmont
Sleeps 2-4 per room
Gorgeously renovated bed and breakfast in this 18th Century farmhouse in the Piedmont region of Italy.
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
Three Terraces
Venice - Veneto
Sleeps 4
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.
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.