24 Gorgeous Italian Escapes

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.

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.


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


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.

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