24 Gorgeous Italian Escapes
Round-ups

24 Gorgeous Italian Escapes

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.

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.

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 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.

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.

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.

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

Trullo Fico

Ostuni - Puglia

Sleeps 9

Gorgeous triple-cone trullo in the heart of Puglia, Southern Italy - designer style, rustic character, true relaxation

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 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.

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.

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.

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.

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.

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 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.

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.


See our full collection of Coolstays in Italy.

Italian Coolstays


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

Type a location to get started