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How to Find the Perfect Vacation Home for Your Trip to Italy

Take a look at what to expect from one region to the next with this expert guide to the Italian vacation market.


Positano coastline, Italy

Vibrant and architectural metropolises, wild and rural landscapes, magical multi-coloured towns perched on the coast, calm lakeside living - Italy has it all. Each region within the sunkissed country has its own vibe and quirks waiting to be discovered. Although it is such a varied landscape, there are some undeniable qualities that the regions share and that you’ll find wherever you stay: a passion for food, stunning views, and the lust for “La Dolce Far Niente”. This Italian phrase roughly translates as ‘the sweetness of doing nothing’ and celebrates the bliss of enjoying the present moment.

Trips in Italy can be as slow or busy as you like. They can be culturally focused, or you could just follow the trail of food - the beauty of Italy is its variety. Most travellers will spend a few days at several different must-see destinations in the country, as part of a bigger trip to get a real taste for each region.

There are some over-arching things to know about vacations (and vacation homes) in Italy. Generally speaking, air conditioning is commonplace, especially in the south of Italy where the temperatures are higher, as well as in busier cities like Venice, Florence, Milan and Rome which can get humid during summer months. The size of vacation rentals in Italy is on the smaller side, especially in densely populated cities (although not as small as elsewhere in Europe such as Paris). If you are staying outside a big town or city, you will need a car to get around. Local public transportation around smaller centres isn't great, so it's worth hiring a car for the ease of exploring. In city vacation homes, don't expect the biggest range of amenities and entertainment (but that's because there's so much to get out and explore). Apart from Milan, the decor of vacation homes within cities is relatively basic – you'll find more design-focused places on the outskirts.

Now, it's time to build your perfect trip with help from our regional breakdown below. We’ve recommended our hero locations to travel to, along with a selection of Plum Guide homes to stay in.


Settle in Tuscany for arguably the finest wine and culture the country has to offer. Florence is considered the birthplace of renaissance art and has unrivalled museums and galleries housing some of the world’s most incredible art. Expect to see Michelangelo’s “David” sculpture, Botticelli’s Birth of Venus, and works by Leonardo Da Vinci and Raphael. Plum Guide home The Old Ford is a stylish central bolthole and has a priceless view, looking directly out onto the Ponte Vecchio, one of the city’s most famous sights. It’s the oldest bridge in Florence and was the only way to cross the river until 1218. Now it’s lined with shops and provides the perfect backdrop for an evening stroll gazing out across the river.

For a more rural setting and painting-like views for days, the Chianti region is an excellent destination choice. It’s bursting with beautiful vineyards, olive groves, and huge Castellos. There’s plenty of vineyard and cellar tours available in the area for you to sample the regional wine. Chianti is an ideal destination if you're looking for a high-end, luxury vacation.

Siena is a medieval town famous worldwide for its horse race, the Palio. This takes place in the Piazza del Campo, twice a year on 2 July and 16 August. There are countless traditional bars and restaurants surrounding the piazza to blissfully while away the hours in, as well as historical buildings to explore. Villa Vin Santo is serenity personified and the perfect base for exploring the area. It has a pool overlooking the rolling hills of Tuscany’s Chianti region.

Plum homes in the area range from £83 per night


If you’re captivated by sea views and prefer wild and unpredictable natural scenery, then the South is definitely for you. For island getaways, choose between Sicily or Sardinia. Compared to the bustling and vibrant areas found in other parts of Italy, these locations are more rustic and earthy. In the south, you'll notice a big trend around converting stables and farmhouses into vacation homes, hotels and holiday resorts, especially in the Apulia region.

Over 2,000km of coastline awaits travellers in Sardinia, as well as thousands of unusual Bronze Age dome ruins, called ‘nuraghi’. The beaches are truly stunning, rivaled only by neighboring Sicily, the largest island in the Mediterranean Sea. Plum home Emerald Isle has breathtaking views of the sea and lots of opportunities for alfresco dining - very much the Sardinian way. In Sicily, archaeological sites and sunbathing opportunities aplenty pepper the landscape, while Europe’s highest active volcano, Mount Etna, towers above the east coast of the city. The region also offers a fantastic selection of organic wine. In the hilltop town of Taormina, an exclusive film festival dating back to 1955 is held annually.

Emerald Isle, Plum Guide home in Sardinia

Emerald Isle, Plum Guide home in Sardinia

The Amalfi Coast is the more glamorous of the Southern hotspots, famous for seafood, lemons, and surreal, beyond-beautiful views. This is popular for those looking to enjoy a traditional European holiday, with lots of American travellers paying a visit. The only way to sensibly get around is by water taxi, to enable you to easily hop between Capri, Amalfi, Positano, and Sorrento. Sorrento faces the stunning Mt Vesuvius and gazes out to the Bay of Naples. There’s plenty of charming narrow streets and cobbled squares to explore. Take a seat and people-watch while drinking a spritz or eating gelato.

The real gem in the Amalfi Coast crown is Positano, a remarkable village stacked in the hillside and meandering down to the sea. It’s renowned for its vibrant nightlife and has attracted the A-list elite for decades. Gaze out to sea from multicoloured buildings, eat the freshest seafood, and enjoy the glow of the deep blue sea on a sunny day. Local delicacies include grilled octopus, fresh clam spaghetti, and unusual native bites such as mozzarella wrapped in lemon leaves. Plum Guide home Terracotta Sunset is situated conveniently between Positano and Sorrento, offering you easy access to both charming towns, while By the Sea in Sicily is practically on the beach, allowing you to be fully immersed in the natural surroundings.

Plum homes in the area range from £179 per night


Crystal clear lakes meet huge mountainsides within this awe-inspiring region, while wild, imposing scenery is scattered with dozens of tiny villages, vineyards, and historical monuments to explore. Lake Como is very much the glamorous and luxe Italian lake resort, favoured by the Hollywood elite; the Clooneys own a home there and it has a starring role in a James Bond film. Plum Guide home Silver Olive looks right out onto the lake and is located on the shores of Moltrasio, Como town is not far by car - travel here for churches, museums, and pretty gardens.

Silver Olive, Plum Guide home in Moltrasio

Silver Olive, Plum Guide home in Moltrasio

If you’re looking for a larger lake, you should settle in Lake Garda - the largest lake in Italy. Many travellers head to Sirmione, a peninsula that juts out in the centre of the lake for picturesque sunbathing, family watersports, and historical castles and ruins. The water-side hotels and accommodation do make it popular with families, but couples seeking peace also flock to the shores of the lake. It’s the perfect location to spend a few nights, usually for a short break of less than a week. Milan and Verona also aren’t far, in case you want to hop around. Enjoying the views, relaxing, and eating well are very much championed in the region - Plum Guide home Castelletto Cleanse echoes this mantra and prioritizes downtime. Its highlights include a spa, sauna, and an outdoor pizza oven. Other homes in the region include Olive Branch, which is surrounded by a 1000-year-old vineyard and a breathtaking infinity pool overlooking Lake Garda.

Plum homes in the area range from £115 per night


Northern cities (with the exception of Venice, steeped in tradition) tend to me more modern than southern cities. Head north to Veneto for romance and Italian history, or Lombardy for sophistication and modernism. Veneto houses Venice and Verona - the former, the country’s famous city-on-water, and the latter where ‘Romeo and Juliet’ is infamously based. Both cities have stunning architecture to explore. In Venice, there’s the floating houses and buildings - a sight to behold in themselves - but also world-renowned architectural triumphs such as St Mark's Basilica. In Verona, you must see the 1st-century amphitheatre.

The cities also share a love for the arts. The Verona amphitheatre hosts the Verona Arena Festival and regular opera performances, while in Venice they host an annual Venice Carnival - the unique costumes and masks of which can be viewed year-round in local shops. Plum home A Touch of Sparkle, in nearby Treviso within Venice, provides a good base to explore the city and its nearby waterways. It’s also situated right by the colourful town of Burano - its buildings are a shocking pop of colour compared to the warm orange hues of Venice’s buildings. Both cities can be explored in a few days and are often best tagged onto the end or beginning of a week-long trip, which can include the lakes region as well.

A Touch of Sparkle, Plum Guide home in Treviso

A Touch of Sparkle, Plum Guide home in Treviso

If you’re looking for a more modern destination in Italy, Milan is the place for you. The fashion and design capital of the country, it’s renowned for its high-class shops and luxe restaurants, from Michelin-starred eateries to designer cafes. Plum Guide home Walls of Shekvati, near Piazza Missori, has a breathtaking view of central Milan and you’ll be right in the action should you stay there. Domus Alba, near Sforza Castle, is a work of art in itself and is a cross between a hall of mirrors and a reconstruction of a Roman temple.

Plum homes in the area range from £72 per night

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