Amazing gastronomy, fabulous wine, picturesque vineyards and spectacular surrounding scenery equal an ideal vacation for wine lovers. With vineyards that extend to all regions of the country — from Alpine vineyards in the far north to the volcanic terroir of Sicily in the south — and its more than 400 varieties of native grape varieties, Italy is one of the oldest and most famous wine-growing countries in the world. The wine regions in Italy are diverse and authentic, representing different and very unique winemaking traditions and heritage. Combining top-quality wines with natural splendour, cultural heritage, and rich gastronomy, Italy ranks as one of the most favourite travel destinations for wine lovers.
We have selected some of the best vacation rentals and luxury villas to rent in Italy for wine and food lovers. Set within great natural and scenic richness and often situated near or on a vineyard, these villas to rent in Italy on vineyards and wine-producing estates allow you to indulge your palate and enjoy the best of the local terroir on your Italian holiday.
LUXURY VILLAS TO RENT IN TUSCANY
A luxury vineyard villa in Tuscany to rent with private pool
Stay on the beautiful Tuscan hills in this luxury vineyard villa to rent in Italy for an extraordinary holiday experience. With stunning views, stylish elegance and peaceful surroundings, this Italy villa is sure to grab your attention.
Nestled in a haven of countryside splendour, the luxury villa to rent in Tuscany sits between luxuriant hills and medieval villages in the middle of the sublime wine landscapes — so there is postcard-perfect scenery in every direction. From its privileged vantage point, you can take in miles of unfolding vistas — waves of greens punctuated by cream-stone buildings.
Decorated with taste and flair, the estate represents a seductive blend of discerning Italian and French style, classic timelessness and stylish modern charisma. Washed wooden floors, traditional exposed beams and arched windows give the house a premium level of luxury, quality and comfort. The distinctive hues are bold yet with a sophisticated restraint. With an appealing ambience of welcoming elegance, the wonderful holiday home features a choice of comfortable living and dining spaces along with six bedrooms, sleeping up to 14 guests.
Conceived to reflect that incredibly desirable al fresco lifestyle, the awe-inspiringly beautiful outdoor area is sure to wow. Set on sprawling private grounds of 10 hectares amidst Leonardo da Vinci’s landscapes of glorious vineyards and gently rolling hills, the holiday villa is a place of utter beauty and tranquillity. Idyllically immersed in the lush greenery of its extensive grounds, the stunning swimming pool forms the centrepiece of the welcoming outdoor oasis. It features a wonderful dining area, a summer kitchen, lovely lounging areas, a Jacuzzi and a vegetable garden.
Located between Florence and Lucca, the estate is close to some of Italy’s most famous landmarks, such as Rome, Naples, Venice and Milano.
Surrounded by nature amidst idyllic vineyards, this wonderful Italian villa for rent in Tuscany is the ideal retreat for wine enthusiasts.
A luxury Tuscan villa rental in the heart of the Chianti wine district
For a luxury Tuscan holiday, renting this luxury villa in the Chianti is the perfect chance to embrace the immensely desirable Dolce Vita lifestyle. Tucked away in the glorious pastoral countryside of Tuscany, enveloped in lush greenery and true privacy, this historic countryside villa holiday rental in Chianti is the ideal getaway for those looking to unwind in beauty and style.
Sublimely positioned, it is a charming, panoramic villa in the rolling hills of Radda in Chianti, Tuscany, that looks out over the vineyards and olive groves. The property boasts a wine cellar, where you can sample wines from the estate. The Carleone wines of the vineyard have been awarded numerous prizes, and its olive oil is known for its delectable taste.
With sprawling grounds of privacy and peacefulness, the aesthetically pleasing property is endowed with immense natural beauty and country charm. The stunning building is gorgeously adorned with a quintessential stone facade and elegantly crafted arched windows. The 19th-century property has preserved its original authentic characteristics and Tuscan charm, while fine injections of stylish modernity and tasteful flair complete the picture. Dazzling with its classy timelessness and quiet elegance, it is conducive to fabulous socialising, lounging and relaxing.
With 900m2 of space galore – accommodating up to 10 guests – the alluringly spacious villa offers days full of delight and privacy. There are five double bedrooms, complemented with elegant living areas and a dining room with seating for up to 12 guests. The impressive chef’s fully equipped kitchen up to the highest gourmet standards with top-of-the-line appliances and impeccable details that impress at every turn. It boasts direct access to a patio designed for outside dining, where you will enjoy gorgeous vistas. The country home also comes with all the comforts and luxuries for fine living, including a mobile bar, Turkish baths, a fully-equipped gym and a caretaker.
Sublimely positioned, the charming property sits in a splendid setting overlooking the wondrous and evocative landscapes of Tuscany. With lovely gardens, shaded corners, sunny terraces and beautiful loggia, there are impressive outdoor spaces for sunbathing, relaxation and socialising. Surrounded by verdant foliage, the delightful, heated pool features plenty of sun loungers and umbrellas. Al fresco dining areas, a barbecue and a pizza oven, are the ingredients for memorable evenings spent enjoying the local delicacies, whether cooked by the guests or by one of the professional chefs. The children’s play area ensures huge amounts of recreational fun for the younger ones.
It is located near the charming town of Radda in Chianti, at the heart of Tuscany’s wine region. Radda is the historical village of Chianti Classico and is a magnificent medieval town. From there, you can easily explore the unique regions of Florence, Siena, San Gimignano and Chianti.
All the most significant Tuscan and Umbrian cities are a two to three hours drive (Lucca, Pisa, Volterra, Arezzo, Cortona, Urbino, Perugia, Assisi, Orvieto, Pienza, Montepulciano, San Gimignano, Vinci, Certaldo….) not to mention the endless number of quaint towns, medieval and Renaissance castles, all within 20 kilometres.
As one of the best county houses in Chianti to rent, it offers a unique opportunity to experience Tuscany’s legendary beauty all year round with family and friends.
LUXURY VILLAS TO RENT IN UMBRIA
Luxury villa to rent in Umbria on a wine estate
A stunning country hideaway, in the idyllic quintessentially Umbrian landscape, amongst gently rolling hills with views of nearby medieval hilltop towns, awaits you at this outstanding wine property in Italy. This elegant holiday villa rental in Umbria is a hymn to all things tasteful and beautiful. Representing the perfect place for an incredible villa holiday in Italy, it is truly a relaxing, heavenly place to savour and enjoy.
The long driveway, dramatically lined with stately cypress trees, leads up to the splendid vacation villa. Guests will marvel at the classic exterior’s impressive stone facade and lovely porches while taking in the breathtakingly beautiful vistas. The wine cellar adds an extra dimension to the villa’s overall attractiveness and desirability. Here, guests can taste a selection of the estate’s site-specific wine releases.
The superbly presented interior exudes a feeling of quiet refinement and restrained elegance in a contemporary yet timeless style. Oversized windows not only blur the lines between indoors and the scenic outdoors but also bring in loads of natural light, creating an incredible sense of luminosity and airiness. With a warm, welcoming ambience to every corner of the home, the understated luxury is evident throughout the villa’s gorgeous living and dining area and six bedrooms, sleeping up to 12 guests. Here, living well is effortless — and always done in tasteful style.
Tucked within the Umbrian countryside, the incredible holiday home is surrounded by gently rolling hills and sweeping vistas of Perugia and lush vineyards. Expansive outdoor spaces encircle the property, including a panoramic sunbathing deck and a sensational infinity pool. Swim a few refreshing morning laps or take a dip at sunset, overlooking uninhibited views of the verdant landscape and vineyards. There are several alfresco areas – including numerous terraces and patios – for entertaining and enjoying quiet moments, all magically beautiful and idyllic.
As far as the eye can see, there is row after row of lush vines in the estate’s vineyards stretching across 65 hectares. It cultivates a variety of grapes for its exclusive wine collection.
Delivering an atmosphere of elegant repose for that truly Italian experience, this stunning wine vacation rental in Umbria successfully unifies the intrinsic beauty of nature with genuine luxury and comfort.
Luxury wine estate villa to rent in Umbria with private pool
Boasting a magically panoramic setting among endless rows of vines, this luxury villa rental in Umbria represents the quintessence of Italy and its timeless beauty.
Encompassed by sprawling grounds and blissful tranquillity, the villa enjoys a privileged position within the 57-hectare wine estate of Decugnano dei Barbi, a leading winery in Umbria. It affords a breathtaking outlook of the wide open expanse of the dazzling surrounding landscape, the Umbrian hills and vineyards. Here the natural splendour is nothing short of postcard-perfect.
A beautiful synthesis of elegance and style, the splendid country estate is impressive in both its generous proportions and timeless distinction. With a genuine sense of history and grandeur, the imposing stone fireplace, the antique furniture, the beamed ceilings and all the details of decorative ironwork add to the immense appeal of the exclusive villa. The light-filled and beautifully presented reception rooms are well suited to fine living and dining. Sleeping up to 10 guests, each of the five en-suite bedrooms provides a private retreat and comfort. You will appreciate thoughtful touches such as bedspreads made of pure cashmere, a choice of different pillow types and Bulgari toiletries.
With emerald lawns and sweeping vineyards, the inviting outdoors captures the perks of a casual and carefree lifestyle. Several sublime al fresco areas offer abundant outdoor living with unlimited socialising, relaxation and dining options. Sit at the loggia with a glass of local wine, savouring the beautiful sunsets and prepare an al fresco feast on the barbecue. The large, dazzling pool, its waters reflecting the blue Umbrian sky, offers serenity and an elevated feeling of luxury. The oversized sun deck is the perfect place for comfort and relaxation, encouraging a sense of escapism.
Situated just outside historic center of Orvieto, one of the most beautiful medieval cities in Italy, and only 90 minutes from Rome and Florence, here premium luxury and a blissful panoramic location are fused into one highly desirable luxury holiday rental in Umbria.
LUXURY VILLAS TO RENT IN SICILY
Luxury Sicily villa for rent for wine enthusiasts
Embraced by the pristine beauty of Sicily’s pastoral landscape, with far-reaching views over the surrounding scenic vineyards and enchanting olive groves, this luxury vacation rental in Sicily provides the irresistible backdrop of Italy’s quintessential dolce vita lifestyle that is so celebrated.
Spreading across idyllic grounds, amongst 10 hectares of vineyards and organic olive groves, the finely crafted home provides an oasis of beauty, bliss and luxury. Abounding in character and comfort, it honours the tradition of historic Italian country properties’ timeless architectural appeal and everlasting beauty. Sympathetically renovated to superb standards, it balances an elegant version of rusticity with the virtues of luxury living. Full of authentic allure and traditional good looks, it is brimming with originality and charisma throughout every turn.
Infused with atmospheric elegance, the good-looking interior is bedecked with a number of gorgeous character features. The home’s arched doorways, exposed wood beams, lovely stone floors, an impressive fireplace and thick stone walls are paired with modern comforts.
With 600m² of aesthetic pleasure and visual tastefulness, the large country home rental in Sicily features a large lounge with a dining room and five lounges furnished with refined Sicilian antiques, ideal for relaxing, dining and socialising. A wood-burning oven adds authenticity and a warm atmosphere to the large kitchen. With space galore, there are 12 beautiful bedrooms for sleeping up to 30 people in comfort.
The holiday villa is available for rent on a self-catering basis. The holiday villa in Sicily can be booked with a private chef, who will use some of the freshest produce from the property’s stunning vegetable garden.
Designed for rest, relaxation and indulging in life’s true pleasures with a calm contemplation, the attractive country house sits idyllically on expansive grounds of 6,000m2, complete with relaxing gardens, terraces, colourful orchards and a magnificent vegetable garden. Providing a sublime escape and serene inspiration, this perfect outdoor environment is highlighted by hypnotising views of the blissful countryside. The fabulous outdoor lifestyle is further enhanced by a lovely swimming pool that is surrounded by lush lawns and plenty of sun loungers. The dreamy sun terrace, embedded in glorious greenery, boasts a backdrop of orange and lemon trees that enrich the magical atmosphere.
Nestled in privacy and beauty within Sicily’s sublimely scenic landscape, the incredible country house for rent in Italy is embraced by a far-reaching panorama with unforgettable views over the surrounding pastoral countryside. It offers guests a break from everyday life, an authentic Sicilian holiday and a perfect base for excursions, relaxation, long leisurely lunches or dinners under the starry sky. The villa’s beautiful surroundings are ideal for taking in captivating vistas while enjoying a glass of wine.
This perfect villa for rent is an ideal getaway for those seeking complete privacy and tranquillity to unwind and revel in peaceful settings. Moreover, it is an excellent base from which to explore some of the best places to visit in Sicily, including its stunning Baroque cities and golden, sandy beaches. Nestled in the countryside of southeastern Sicily, the holiday villa is just a few kilometres away from Ragusa Ibla, Modica, Scicli and Punta Secca.
Then there are many of Sicily’s top must-see sites — and historic towns such as Syracuse, Catania, Taormina, Agrigento or Caltagirone — within easy reach that will make for enjoyable and fascinating day trips. From the villa, guests can enjoy various walking or cycling routes amid the natural beauty of the countryside.
Offering a peaceful, joyful and enchanting experience, this large country house rental in Sicily gives its guests an authentic feeling of luxury, comfort and contentment.
Indulge in a wine lover’s paradise with our curated collection of the best vineyard villas to rent in Italy. Immerse yourself in the rich tapestry of Italian winemaking as you wake up to breathtaking vineyard views, explore historic cellars, and sample exquisite wines. From Tuscany’s rolling hills to the sun-kissed shores of Sicily, each villa offers a unique blend of luxury, comfort, and the allure of Italy’s wine regions. Whether you seek a romantic getaway or a group escape, these exceptional villas provide an unforgettable experience where the art of winemaking and the beauty of the Italian countryside converge. Book your luxury villa rental from Villanovo today and embark on a journey of wine, luxury, and pure indulgence.