Home to an array of UNESCO World Heritage Sites, rich culture, mouth-watering cuisine and stunning coastlines – it’s no wonder Italy is the 5th most visited country in the world! So, whether you want to explore historical monuments some days and catch a tan the next, there’s something for everyone here. And it gets better, our luxury villas in Italy can take your Italian escape to new heights. If you’re in need of sun in Sicily, a villa with a pool in Puglia or a tremendous Tuscan view; our top 10 popular villas in Italy won’t disappoint – bellisima! 

1. Villa La Ganza, Sicily

Villa La Ganza - Sicily - Oliver's TravelsThe uber-modern Villa La Ganza is perched on a quiet hill with gorgeous panoramic views of Sicily’s coastline – perfect for soaking up from the privacy of your very own pool. Once you’ve had your fix of sun and scenery, take a day trip down to the UNESCO World Heritage Sites of Ragusa, Modic and Scicli. Then, when you’ve tired yourself out from exploring, come back home and kick back in the hot tub with a glass of red – you deserve it!

Sleeps: 8-12

Price from: £47pppn

2. Casa Fiastrone, Le Marche

Casa FiastroneA classic countryside retreat, Casa Fiastrone is surrounded by lush green vistas and boasts a stunning backdrop of the Sibillini Mountains. Its 1.5 hectares of private countryside allows little ones to head off on their own adventures while the adults relax by the pool, while the lovely dining spaces allow you all to come together for an alfresco barbeque.

The villa interior encourages those bonding moments too, featuring an open-plan design with bright and airy spaces – ideal for those large group getaways! However, if you really need an hour or so to yourself, grab a book and head to the hammocks, soaking up the sun as you truly decompress.

Sleeps: 14

Price from: £26pppn

3. Tenuta Montanaro, Puglia

Tenuta MontanaroSurrounded by vineyards and manicured gardens, Tenuta Montanaro is designed in the traditional conical shape of Puglia. When you arrive, you’ll find some chilled bottles of local white wine waiting for you – the perfect way to begin your Italian adventure.

Once you’ve settled in, feel free to ask the owner for some local tips on how to make the most of your stay. However, here’s one from us first: picture-perfect Locorotondo is only 4km away, and it’s a great place to spend an afternoon winding around laneways of whitewashed houses, cafes and charming churches.  

Sleeps: 6

Price from: £32pppn

4. Villa Dania, Tuscany

Villa Dania

This family-friendly home is one of our most popular villas in Italy and invites connection and conversation. Sit with friends by that irresistible pool, under the arbour, or inside under a fresco (yes, really). All that’s missing is a glass of good Tuscan wine. Thankfully that can be found in the village with a couple of shops and places to eat, just a short stroll from the villa itself… that’s if you can tear yourself away from the incredible vineyard views from the terrace.

Sleeps: 13

Price from: £66pppn

5. La Dolce Vita, Sicily

La Dolce VitaThis 19th century farmhouse has remained in the hands of one Sicilian family for generations. While it may have been recently renovated, all the traditional character remains, boasting a vast terrace, stone structure and carved ceilings. Our favourite thing to do here is enjoy breakfast beneath the shade of the many fruit trees, dining alfresco as you look out over the surrounding countryside. 

Don’t miss the chance to visit nearby Modica, Scicli and Noto, plus many of Sicily’s archaeological treasures that are just waiting to be uncovered.

Sleeps: 16

Price from: £19pppn

6. Villa Cecconi, Tuscany

Villa CecconiBring all of your closest friends and family together in this former 14th century watchtower. Perfectly placed for exploring nearby Siena and Florence, this elegant home is lined with cypress trees and rose bushes – but that’s just the start. You’ll also enjoy sweeping views over the surrounding vineyards, stretching all the way to San Gimignano.

When you’re ready to head inside, choose from three separate buildings so that everyone can have their own space to unwind, coming together again at the large dining table on the lawn.

Sleeps: 14-24

Price from: £50pppn

7. Villa Todari, Umbria

Villa TodariThis traditional 19th century villa is the ultimate Italian countryside retreat; surrounded by gardens, olive groves and rolling hills but still only 45 minutes from Rome, it offers the best of both worlds. Stone walls, stylish furnishings and terracotta tiles adorn the interiors, contributing plenty of character. Meanwhile the private swimming pool overlooks the gorgeous surrounding countryside – perfect for taking in over sunset cocktails.

Sleeps: 6-10

Price from: £56pppn

8. Masseria Monte Piccinnu, Puglia

Masseria Monte PiccinnuThis recently renovated Puglian home is found in the serene countryside of Italy’s heel. With a modern-meets-traditional aesthetic, it’s surrounded by luscious olive groves and boasts light, airy living spaces – perfect for getting together each evening. Our favourite features include the bio-pool, which is purified by plants, plus the alfresco terrace.

When you’re ready to venture a little further, drive just 5 minutes away to find the charming ancient town of Ceglie Messapica. Cobbled streets and characterful cafes await you, making it easy to spend an afternoon aimlessly ambling.

Sleeps: 10-14

Price from: £89pppn

9. La Tenuta, Venice & Veneto

La Fiorita

Not far from magical Venice, this villa is stylishly decorated and comes equipped with state-of-the-art facilities – all while retaining its traditional charm. Boasting a heated swimming pool, high-tech gym, wellness spa with Turkish bath and sauna, this is our number one wellness pick. If you can tear yourself away for an afternoon, take a trip to the region of Veneto – it’s well-known for wine-tasting, cycling, hiking and golf.

Sleeps: 8

Price from: £220pppn

10. Villa Diadema, Puglia

Villa DiademaThis enchanting villa in the Puglian countryside is surrounded by beautiful nature – private woodlands, olive groves, Mediterranean plants and even a natural underground grotto! It’s ideal for children who love exploring and letting their imaginations run wild, while adults can enjoy the outdoor pool and sunken pool bar. Hire a Michelin-starred chef from one of the nearby restaurants to enjoy top-quality cuisine from the comforts of home, or take a short walk to dine in for an authentic experience.

Sleeps: 12

Price from: £47pppn

If you’re heading off to Italy soon, be sure to check out our guide to gorgeous towns and villages in Tuscany, and our local’s guides to Umbria and Sicily. Of course, these properties are just the tip of the iceberg, we’ve got loads more incredible villas in Italy to choose from! If you need some advice on choosing, give our concierge team a call to point you in the right direction.

Are you already dreaming of your 2024 villa holiday? You should check out our trending destinations here:

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