The Best Villas in Italy for Multi-Generational Summers

0203 1891381

9 of the best Italian

villas

for a long, lazy summer with the family

There’s an unmistakable pull to Italy each summer—the kind that has people flocking from all over, craving the sun-drenched landscapes, rich history, and, of course, the food. For many, the dream is to take over an Italian villa, letting the whole family indulge in La Dolce Vita.

From Tuscany’s undulating hills to the dramatic coastlines of the Amalfi Coast, Italy offers villas with the perfect balance of space and luxury, where every member of the family, from toddlers to grandparents, can escape, unwind, and connect.

Italy is, without question, a country that welcomes large families — with villas that offer the room to gather, yet enough quiet corners for personal space. In Tuscany, you’ll find villas nestled among vineyards that stretch to the horizon, their ancient facades still holding the whispers of centuries gone by. But beyond the familiar, there are hidden gems: lesser-known regions where the landscapes remain untouched and the crowds few, giving you an opportunity to experience the real Italy, away from the buzz of the tourist trail.

Across the country, from Sicily to Sardinia, the variety of villas is striking. You’ll find everything from grand palazzos with sweeping views of the Mediterranean to traditional farmhouses, beautifully restored, with stone walls that tell stories of generations past. Whether you’re drawn to the grandeur of an aristocratic estate or the charm of a smaller, intimate retreat, Italy’s villas offer a host of possibilities, each with its own unique allure.

What elevates a villa holiday is the chance to make it entirely yours. Imagine starting your day with a breakfast prepared by a private chef using only the freshest ingredients from local markets, followed by a leisurely tour of the region with a local historian who’ll share fascinating insights. For those who like a little adventure, a cycling guide can show you secret paths through olive groves, while personal trainers ensure you’re feeling your best with tailored sessions designed to refresh and recharge. And if a glass of wine while overlooking the hills sounds tempting, a private sommelier could be at hand to guide you through the best local selections.

At Swords Travel, we curate every detail of your Italian villa experience, from bespoke culinary experiences to expert-led excursions, ensuring that your family’s needs and desires are met with precision. These are a few of our favourite villas, perfect for your well-deserved long, lazy summer…

1. Villa La Querce,

Castelfalfi

LOCATION:

Tuscany

SLEEPS:

10

Set high in the hills of Florentine Chianti, Villa La Querce is a sophisticated villa that brings together the best of Tuscany’s timeless charm with modern design. Renovated with exceptional attention to detail, the villa showcases a seamless blend of wood and stone, creating a warm yet contemporary feel that invites relaxation and connection.

Inside, the spacious living areas offer both comfort and style — whether you’re curled up by the fire in one area or enjoying a film on the large screen in another. The state-of-the-art kitchen is perfect for those wanting to indulge in Tuscan cuisine, whether you’re preparing your own feast or taking a cooking class with local ingredients. For a little fun and friendly competition, there’s a playroom with a billiard table and table football to keep everyone entertained.

Outside, the infinity pool mirrors the villa’s grand façade, offering panoramic views over the surrounding golf course and the majestic Castle of Castelfalfi. Accommodating up to 10 guests, Villa La Querce features four spacious double bedrooms, each with an en suite bathroom, as well as a twin bedroom with a private bathroom. Whether you’re lounging by the infinity pool or enjoying family time in the heart of Tuscany, this villa offers an unforgettable stay.

2. Villa Musa,

Lake Como

LOCATION:

Lake Como

SLEEPS:

12

Nestled on the west shore of Lake Como, Villa Musa offers over 700 sqm of elegant space, perfect for family and friends seeking a luxurious lakeside escape. The villa’s prime location offers stunning views over the lake and easy access to the natural beauty of the region, along with day trips to Como and Milan.

The standout feature is the panoramic swimming pool, where you can swim or relax while soaking in the, quite-frankly, jaw-dropping scenery. For extra indulgence, a Jacuzzi offers the perfect spot to unwind. Alfresco dining areas, where meals are prepared by a local chef, complete the experience.

Accommodating up to 12 guests, the villa has 6 double bedrooms with en-suite bathrooms. Two bedrooms are on the ground floor, along with a living area with a TV, pool table, and bar corner. The first floor features a fully equipped kitchen, dining room, and living room opening onto a terrace with lake views. The remaining four bedrooms are on the second floor.

With its stunning pool, gorgeous views, and luxurious design, Villa Musa offers the ultimate Lake Como getaway.

3. Casa Colonica,

Florence

LOCATION:

Tuscany & Florence

SLEEPS:

10

Casa Colonica offers the privacy of a standalone villa with all the perks of Villa La Massa, a storied Medici-era estate turned five-star resort on the banks of the Arno. Just outside Florence, this is where Renaissance charm meets contemporary luxury, with grand architecture, lush gardens, and a sense of timeless elegance.

The villa itself is steeped in history—during restoration, a 16th-century oven was uncovered, a quiet reminder of Tuscany’s rich past. Today, it’s a sophisticated retreat with four stylish suites (sleeping up to 10 guests), blending rustic terracotta floors and wrought-iron details with warm, elegant interiors. The private courtyard is perfect for al fresco dining, while the villa’s kitchen allows for relaxed, home-style meals.

Guests of Casa Colonica have full access to Villa La Massa’s exclusive amenities, including a serene riverside pool, an indulgent spa infused with local botanicals, and gourmet dining showcasing the best of Tuscan produce. For those craving adventure, there’s white truffle hunting, Chianti wine tastings, and medieval towns like San Gimignano just a short drive away.

4. Masseria Pettolecchia,

Puglia

LOCATION:

Puglia

SLEEPS:

10

Tucked away in the olive-strewn landscapes of Puglia, Masseria Pettolecchia is where countryside charm meets understated luxury. Originally built in 1800 as a noble retreat, this five-suite estate has been transformed into a sophisticated hideaway, offering everything from a private heated pool to complimentary access to Pettolecchia Il Lido, an exclusive beach club.

Wake up to the scent of ancient olive trees, pick fresh produce from the estate’s organic garden, or take a morning cycle along the coast with the villa’s complimentary bikes. Days here are effortlessly indulgent—whether it’s lounging by the L-shaped pool, dining al fresco beneath a shaded pergola, or heading to the beach in your private Lexus. Inside, the five individually designed suites blend heritage details with modern comfort, each featuring a double bed, en suite bathroom, and walk-in wardrobe. The villa sleeps up to 10 guests, plus one additional toddler, with ground-floor suites opening onto the terrace and first-floor bedrooms offering sweeping garden views.

From Romanesque cathedrals to whitewashed hilltop towns, Masseria Pettolecchia puts Puglia’s best within easy reach—though with dedicated staff on hand and space to truly unwind, you might not want to leave.

5. Casale Cetena,

Siena

LOCATION:

Tuscany

SLEEPS:

16

Set amid rolling vineyards and olive groves near Siena, Casale Cetena is the ultimate Tuscan retreat for larger gatherings. Whether it’s a milestone birthday, an intimate wedding, or a sun-drenched family reunion, this beautifully restored farmhouse provides the perfect setting for a celebration in the heart of Tuscany.

Designed for togetherness, the villa’s central living and dining areas open onto a pergola made for long, leisurely meals under the Tuscan sky. A professional-grade kitchen invites culinary experiences—whether it’s a private chef-prepared feast or a hands-on cooking class. Outside, the heated infinity pool offers breathtaking countryside views, while the landscaped gardens provide endless spaces to gather and unwind.

Casale Cetena sleeps up to 16 guests across eight spacious en suite bedrooms, split between two buildings for added privacy. The main house features an elevator connecting all three floors, making it easily accessible for all generations. With ample room to spread out yet plenty of inviting communal spaces, this is the perfect villa for multi-generational escapes where lifelong memories are made.

6. Villa Settefrati,

Sicily

LOCATION:

Sicily

SLEEPS:

12

Set above Sicily’s northern coast with sweeping sea views, Villa Settefrati is a serene escape designed for laid-back living and those long, lazy summers we all dream of. Overlooking Cefalù and the shimmering Tyrrhenian Sea, this beautifully restored villa blends timeless charm with contemporary comfort.

The main house sleeps up to 8 guests across four en suite double bedrooms, while a separate annex, 150 metres away, offers space for 4 more, making it perfect for groups who may want a little extra privacy. Inside, elegant yet modern interiors contrast with the villa’s traditional façade, featuring bright spaces, a cosy lounge with a fireplace, a fully equipped kitchen, and striking ceramic flooring.

Outside, a panoramic terrace with incredible views sets the scene for al fresco dining, while a private stepped path leads to the sea, where guests can enjoy both an accessible beach and a secluded sandy cove. A swimming pool, shaded patio, and spacious lounge complete this stunning escape—perfectly placed for exploring Cefalù, Palermo, and the wild beauty of Madonie National Park.

7. Villa Santa Croce,

Umbrio

LOCATION:

Umbrio

SLEEPS:

6

Perched atop Mont Santa Croce, Villa Santa Croce offers a serene and stylish retreat, ideal for smaller groups or a family looking to escape the everyday. With sweeping views over the Umbrian countryside, the villa is designed for relaxed, al fresco living. The impressive infinity pool and multiple terraces set the stage for days spent soaking up the sun, reading a book, or planning your next adventure.

Nestled within a private country estate, Villa Santa Croce is the perfect base to explore the beauty of Umbria. You’re within reach of hiking, cycling, and fishing, and for a truly authentic experience, enjoy a cooking class, pizza-making session, or wine tasting. Alternatively, take advantage of the villa’s fully-equipped kitchen to whip up your own meals or opt for a private chef to prepare something special while you dine outdoors and take in the view.

The interiors are understated yet chic, featuring a neutral color palette that complements the natural surroundings. The villa sleeps up to six guests across three spacious en suite bedrooms, all with king-sized beds and fine cotton linen. The master suite features a four-poster bed and a private balcony with views of the valley.

Outside, the panoramic infinity pool awaits, with pool heating available on request. Unwind in the superb teak hammock or enjoy a meal under the pergola. With all the comforts you need for a truly relaxing stay—air conditioning, Wi-Fi, concierge service, and a 20% discount at the estate’s championship golf course—Villa Santa Croce is the perfect haven for those seeking peace and privacy.

8. Villa Braga,

Lake Como

LOCATION:

Lake Como

SLEEPS:

16

Villa Braga is a captivating 19th-century property that blends historical grandeur with modern comforts, offering a private and peaceful retreat on the shores of Lake Como. The villa’s elegant interiors are warm and romantic, with spacious living areas that invite relaxation and celebration. Its beautifully landscaped gardens, featuring terraced flower beds and a serene natural waterfall, create a tranquil atmosphere that perfectly complements the panoramic views of the lake.

The villa boasts a heated swimming pool and outdoor jacuzzi, providing the ideal space for relaxation while soaking in the stunning lake views. Guests can also enjoy the convenience of private boat moorings, allowing for lake exploration at their leisure. For a more active experience, the villa offers stand-up paddleboarding and access to a pathway leading to the charming village of Torno.

Villa Braga accommodates up to 16 guests across 9 bedrooms—7 in the main villa and 2 in the guesthouse. Each bedroom is beautifully appointed with en-suite or private bathrooms, ensuring privacy and comfort for all. The villa features two fully equipped kitchens, ideal for preparing meals or enjoying a private cooking class in the comfort of your own home. The living areas are designed for comfort, with panoramic views, and are complemented by a gym, game room, table tennis, and pool table to keep everyone entertained.

9. Casale Gioconda,

Chianti

LOCATION:

Tuscany

SLEEPS:

22

Casale Gioconda is a spacious, family-friendly retreat nestled in the rolling hills of the Chianti countryside, where rows of vineyards produce the villa’s own wine, stored in a private cellar for your enjoyment. The villa blends traditional Tuscan charm with modern comforts, featuring wooden beam ceilings and exposed stonework that give it a timeless, welcoming feel. It’s the perfect spot to unwind with loved ones, enjoy local wines, and immerse yourself in the beauty of the Tuscan landscape.

With nearby Chianti’s charming towns, local markets, and excellent restaurants, the villa offers a fantastic location to explore the best of the region. Whether it’s hiking through the countryside, sampling local delicacies, or visiting family-run wineries, you’ll feel connected to the true heart of Tuscany. At the villa, you can kick back by the panoramic pool, explore the expansive gardens, or enjoy quality time in the pergola, complete with a ping-pong table, or gather for movie nights in the cinema room.

This villa can comfortably accommodate up to 22 guests, making it a great choice for large families or groups of friends. The four-story property includes 5 master bedrooms, each with king or queen-sized beds, en-suite bathrooms, and plenty of space to relax. There are also 3 family suites with a mix of queen-sized and twin beds. The fully equipped kitchen on the ground floor is perfect for preparing meals together, and the large dining area provides ample space for everyone to enjoy a meal. Outdoor dining areas include a barbecue and wood-burning pizza oven—ideal for casual dinners under the Tuscan sky.

Start your Italian

Summer

At Swords Travel, we understand that finding the perfect villa goes beyond luxury—it’s about crafting an experience that checks every box on your list. Whether you’re planning a multi-generational family getaway, an intimate escape, or a special celebration, we’re here to help you find the ideal villa to suit your unique needs and desires.

From private chefs who’ll prepare exquisite meals just for you, to vintage cars for exploring the local countryside in style, our partners offer a curated selection of unforgettable experiences. Indulge in boutique shopping trips, personalised wine tastings, or sports and leisure activities. For families, our partners can arrange everything from private treasure hunts to kids’ cooking classes, ensuring everyone has a memorable time.

At Swords Travel, we’re dedicated to making every moment of your journey tailored to you. With expert guidance and exclusive access to some of the world’s most stunning villas, we’ll help you turn your dream holiday into a truly exceptional experience.

To enquire about these breathtaking villas call
0203 907 1100 or start planning your trip below.

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