Planning a group trip to Italy? You’re probably dreaming of La Dolce Vita – eating fresh pastries for breakfast and swimming in vineyard-surrounded pools – but feeling overwhelmed by the logistics. Finding rental villas in Italy for large groups is surprisingly tricky, especially when you want everyone to stay together without breaking the bank or settling for cramped quarters.
We have helped families and friend groups plan their Italian getaways, and we know exactly what makes or breaks a group vacation. Whether you’re organizing a milestone birthday or reunion, or just want to escape together, the key is choosing the right type of accommodation that gives everyone space to spread out while keeping the group connected.
We’re sharing our curated collection of Italy’s best group villas – from coastal retreats on the idyllic island of Sardinia to sun-soaked holiday houses with panoramic views of Tuscany’s rolling hills. These aren’t just beautiful properties; they’re spaces designed to bring people together for truly unforgettable experiences.
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Best Italy Holiday Villas for Groups
Tuscany
1. Villa Ardore
Sleeps 16: Eight bedrooms and 10 bathrooms across two private villas
Nearest airport: Florence Amerigo Vespucci Airport (48.6 km/30 miles, 49-minute drive)
What do you picture when you imagine the perfect villa in Tuscany? Perhaps you dream of renovated rustic country houses hidden behind cypress trees. Maybe it’s surrounded by vineyards that stock the villa’s cellar with fine wine. Of course, no upmarket villa would be complete without a pool to cool off under the hot Tuscan sun.
Villa Ardore has all of this and so much more. Family members won’t need to run and stake their claim. All air-conditioned bedrooms are beautiful with an attached bathroom. Relax in the spacious living room and create traditional Italian dinners in the two well-equipped kitchens and pizza ovens. It’s a private villa, so your group will be the only ones staying on the estate.
Every breakfast is catered and modern comforts like Wi-Fi internet are a given. Make your villa stay special by booking private chef services or a sommelier through the concierge for an extra cost. Larger groups looking for luxury villas don’t need to look any further.
CLICK HERE TO CHECK RATES AT VILLA ARDORE
2. Al Gelso Bianco
Sleeps 41: 8 apartments for 3-6 people booked separately
Nearest airport: Florence Amerigo Vespucci Airport (44.3 km/27.5 miles, 44-minute drive)
Al Gelso Bianco is a family-run country resort with a collection of large villas and apartments. There will be no need to leave once during your vacation if you don’t want to! With a large 60-hectare estate, you can spend your days stomping through the beech forest, swimming in the pool, getting a massage, or tasting home-grown wine, honey, and olive oil.
The apartments are modern and comfortable. Feel free to request cribs, highchairs, and extra equipment your group might need. Al Gelso Bianco’s breakfast buffet caters to all tastebuds. Dinners can be included in your booking during the summer months.
Luxury villa holidays in Italy often include special activities but Al Gelso Bianco goes the extra mile for large families travelling with kids. Children can help feed the hens, enjoy the playground, go horseback riding, take cooking classes, join a truffle hunt, or visit the llama farm. There are even babysitting services so you can enjoy adults-only quality time.
CLICK HERE TO CHECK RATES AT AL GELSO BIANCO
3. Tenuta Guardastelle
Sleeps 26: 5 apartments for 2-4 people plus 4 suites with max. 3 people each booked separately
Nearest airport: Florence Amerigo Vespucci Airport (59.3 km/37 miles, 52-minute drive)
One of the best Italy holiday villas for groups looking for a great place in the countryside with easy access to lively small towns like San Gimignano should check out Tenuta Guardastelle. It’s not a private villa so you can book as many suites as you need for your group holiday. This is the perfect choice for a family reunion in Italy if people are on different budgets and you’d prefer separate spaces.
Tenuta Guardastelle is a 15th-century former farm estate turned into a collection of villas. Each apartment and suite has retained original features like exposed beams and terracotta tiles without a TV in sight. Don’t worry, there’s still Wi-Fi and air conditioning!
Expect a delicious breakfast with a huge spread of local produce. You can dine on the terrace overlooking San Gimignano and the estate’s vineyards and olive groves.
If you’re looking for Italy villas with pool access, Tenuta Guardastelle checks that box too. Saving a sun lounger with a towel is unnecessary as the friendly staff ensures every guest has easy access to a chair whenever they like. Don’t leave without touring the estate’s wine cellar and tasting the fruits of their vines.
CLICK HERE TO CHECK RATES AT TENUTA GUARDASTELLE
4. Mormoraia
Sleeps: Plenty of rooms that sleep 2, 3, and 5 guests with ensuite bathrooms booked separately
Nearest airport: Florence Amerigo Vespucci Airport (61.8 km/38.4 miles, 56-minute drive)
Another beautiful villa near San Gimignano is Mormoraia. This Tuscan resort offers affordable luxury for larger groups of friends (it’s the perfect place for couples) seeking Instagrammable design-led interiors. Think soaking tubs in the bedrooms, stunning views outside every window, and a rustic elegance you can only find in the best rental villas in Italy.
One of the best things about Mormoraia is its onsite restaurant and winery. Il Fienile Restaurant offers a locally sourced menu with a modern twist. Arrange a private wine and extra virgin olive oil tasting and take home Mormoraia labeled bottles as a souvenir. Oh, and did I mention the infinity pool and sauna?
CLICK HERE TO CHECK RATES AT MORMORAIA
Rental Villas in Italy – Umbria
5. Altarocca Wine Resort (Adults Only)
Sleeps: Rooms sleep 2 guests with ensuite bathrooms booked separately
Nearest airport: Leonardo da Vinci–Fiumicino Airport in Rome (156 km/97 miles, 1 hour and 57-minute drive) but Florence Airport is another option
Finding beautiful villas equidistant from Florence and Rome airports to accommodate big groups traveling from different places can be tough. Luckily, the Altarocca Wine Resort is the perfect villa complex near the major cities of central Italy. The rooms are spacious with lots of natural light and some open directly into the property’s large garden.
This Umbrian spa hotel offers everything you could possibly be looking for in an adults-only group vacation. We’re talking multiple pools and hot tubs, a gym with panoramic views of the olive groves and vineyards, and two onsite restaurants. Don’t miss the “vinotherapy” treatment at Altarocca’s Wine Spa.
CLICK HERE TO CHECK RATES AT ALTAROCCA WINE RESORT
6. Castello di Reschio Bell’Aria
Sleeps 12: Six bedrooms and six bathrooms in one private villa
Nearest airport: Florence Amerigo Vespucci Airport (151 km/93.8 miles, 1 hour and 54-minute drive)
It’s fitting that Castello di Reschio Bell’Aria is located so close to the cinematic town of Cortona made famous in the memoir Under the Tuscan Sun. This multi-generational family farmhouse turned luxury villa looks like an idyllic country home right out of a Hollywood movie! You’ll struggle to find other Italy villas to hold a candle to this one.
Castello di Reschio Bell’Aria is the perfect setting to celebrate any milestone event. It’s a tastefully renovated country estate with traditional features like Juliet balconies, a library, and an old bread oven. This villa strikes the perfect balance between old-world style and modern elegance.
The concierge service can arrange both onsite activities and excursions. Play matches on the private tennis courts, take horse riding lessons, and enjoy wine tasting. Venture to popular destinations in the Umbrian and Tuscan countryside like Arezzo, Perugia, and Siena. Families can huddle around the outdoor fire pit or splash around in the private pool. With a maid service and guard, you can truly relax here.
7. Villa Baiocco
Sleeps 16: 7 bedrooms and 8 bathrooms in a private villa
Nearest airport: Florence Amerigo Vespucci Airport (146 km/91 miles, 1 hour and 46-minute drive)
Villa Baiocco is one of the best large villas in Umbria for big families or friends who want to spend as much time together as possible. With ensuite bathrooms next to every bedroom, you can do so without fighting for showers! This villa has warm, comfortable interiors with multiple dining, living, and kitchen areas.
Choose a private cook service, or organize meals yourselves. Book local excursions through your host, or spend your days relaxing by the large private pools and hot tub. Villa Baiocco is the perfect choice for laid-back groups.
CLICK HERE TO CHECK RATES AT VILLA IL BAIOCCO
8. Villa Rosaspina
Sleeps 8: 4 bedrooms with 4 ensuite bathrooms in a private villa
Nearest airport: Rome Leonardo da Vinci–Fiumicino Airport (164 km/102 miles, 2 hour and 8-minute drive)
Villa Rosaspina is one of those holiday homes that will make you feel like you’ve been transported back in time. This beautiful property dates back to the 1700s. While the heavy wooden furniture and stone fireplace hark back to yesteryear, the air-conditioning and appliances are all ultra-modern!
This secluded villa is surrounded by lush forests meaning you can use the private swimming pool in peace. Sleep in rustic chic suites before waking up to eat breakfast on the covered terrace. There’s no shortage of outdoor nooks to escape with a good book or spaces to enjoy game nights and group meals.
CLICK HERE TO CHECK RATES AT VILLA ROSASPINA
Puglia Holiday Rentals for Groups
9. Le Rose Trullo Villa
Sleeps 9: 4 bedrooms and 4 bathrooms in a private villa
Nearest airport: Bari International Airport-Karol Wojtyla (100 km/62 miles, 1 hour and 12-minute drive)
Trulli houses are UNESCO-certified traditional homes with conical roofs made from limestone boulders. These dwellings are found in the southern region of Puglia and many are vacation rentals. Staying in one is such a fun, authentic experience!
Mid-sized groups will love staying in Le Rose Trullo Villa. This larger-than-usual trullo sits on a two-acre olive grove with a private pool and sauna. Its biggest selling point is the outdoor spaces with an alfresco kitchen and bar set-up. The ancient pizza oven is still in full working order. Inside, the decor has been updated with modern appliances but the exposed stone and original doors maintain the original charm.
CLICK HERE TO CHECK RATES AT LE ROSE TRULLO VILLA
10. Trullo of Jay
Sleeps 7: 3 bedrooms and 1 bathroom in a private villa
Nearest airport: Bari International Airport-Karol Wojtyla (70 km/43.4 miles, 1-hour drive)
Want to stay in a more traditional trullo that’s still big enough for a small group? Trullo of Jay is a great affordable option that still has luxurious touches.
It’s an 18th-century home with modern appliances, comfortable beds, and even a swimming pool. You’ll need it too cool off in the baking Puglia summers! Take advantage of the BBQ grill and covered terrace by cooking group dinners while enjoying a glass of local wine as the sun sets.
CLICK HERE TO CHECK RATES AT TRULLO OF JAY
11. Trullo Pia
Sleeps 10: 3 bedrooms and 3 bathrooms
Nearest airport: Bari International Airport-Karol Wojtyla (59.4 km/37 miles, 45-minute drive), nearest towns are Alberobello and Monopoli.
Trullo Pia is a magical escape in the Apulian countryside. Surrounded by olive groves and fruit trees, the property even has a vegetable garden and swimming pool for cooling off during hot Italian summers.
Recently renovated, the property can accommodate six people in 3 bedrooms, plus another 4 people in the two sofa beds located in two separate living rooms. The rooms, all in Trullo, are all very spacious and equipped with air conditioning.
CLICK HERE TO CHECK RATES AT TRULLO PIA
Sardinia
12. Villa Ursula
Sleeps 10: 4 bedrooms and 4 bathrooms in a private villa
Nearest airport: Cagliari Elmas Airport (246 km/153 miles, 2 hour and 30-minute drive)
Nothing compares to an island escape where you can wake up to a sea view every morning. No wonder some of Italy’s best holiday villas are in Sardinia! Villa Ursula is minutes away from the bustling city of San Teodoro and the Tyrrhenian Sea, so you have the best of both worlds.
This spacious, modern villa is a fantastic base for exploring the north of the island as a group. Enjoy multiple outdoor spaces for dining. Ample bathrooms are essential for not getting on top of each other throughout your stay!
CLICK HERE TO CHECK RATES AT VILLA URSULA
13. Torre delle Stelle Villa
Sleeps 20: 10 bedrooms and 10 bathrooms in a private villa
Nearest airport: Cagliari Elmas Airport (44.3 km/27.5 miles, 50-minute drive)
Larger groups can stay within easy reach of the airport on this rare beachfront property. Torre delle Stelle Villa is literally right on the beach – within a few steps! – with safe shallow waters for groups with children. There’s also a pool so you can have your pick of places to swim. There’s no need to worry about privacy due to the trees and the raised position of the villa.
Every bedroom is decorated with soft whites and rattan wood furniture like a quintessential Mediterranean vacation home. You’ll find quirky touches like shell-shaped sinks and a dreamy stone spa. Torre delle Stelle Villa is practical as well as beautiful with large dining areas, inside and out, so you can have the best time in Sardinia altogether.
CLICK HERE TO CHECK RATES AT TORRE DELLE STELLE VILLA
Italian Lakes
14. Villa Prestigio
Sleeps 14: 8 bedrooms and 11 bathrooms in a private villa
Nearest airport: Milano Malpensa Airport (84.7 km/52.6 miles, 1 hour and 20-minute drive)
If you have ever dreamed of a Lake Como vacation, Villa Prestigio is everything you’d expect in such a trendy, sought-after destination. Stylish mid-century modern interiors complement the infinity pool and panoramic view of Lake Como and surrounding mountains. It’s truly breathtaking. Everyone gets a comfortable queen or double bed so there are no arguments.
Despite the mountainside location, there’s a surprising amount of outside space. Everyone can watch the sun set from the wraparound balcony/terrace. Head to the pool house in the evenings where there is a kitchen bar and a pool table and plenty of seating. As you can probably tell, this Italian villa is best suited for adults-only groups.
CLICK HERE TO CHECK RATES AT VILLA PRESTIGIO
15. Palazzo San Daniele
Sleeps 16: 9 bedrooms and 9 bathrooms in a private villa
Nearest airport: Verona Valerio Catullo Airport (34 km/21 miles, 35-minute drive) and Venice Marco Polo Airport is also close
Swap the elegance of Lake Como for the chill vibes of Lake Garda. Palazzo San Daniele is located just outside Punta San Vigilio and boasts a small beach. While the exteriors stay true to its 19th-century roots, the interiors of Palazzo San Daniele are contemporary with stunning chandeliers and luxurious rooms.
Large groups can make full use of the movie room, games room, sauna, and several outdoor dining spaces. When you’re not enjoying the lake, you can swim in or relax by the private pool.
CLICK HERE TO CHECK RATES AT PALAZZO SAN DANIELE
Book the Best Rental Villas in Italy for Your Group Vacation
Luxury Italian villas are the perfect accommodation for large groups traveling together. You can eat communal buffet breakfasts at your own al fresco dining area and catch up around your private swimming pool. No matter where you stay, you can expect pastoral views and easy day trips to charming ancient villages.
Booking one of these Italy holiday villas for groups is the best way to have a special celebration that includes everyone, whether that’s your large family, a large group of friends, or a mix of both!
About the author: Kirsten is a family travel expert who has been traveling with kids for over 20 years. She has been featured in Travel & Leisure, Parents Magazine, AFAR, Vogue, NBC, Lonely Planet, and Thrillist, to name a few. Kirsten is also the content creator behind Kids Are A Trip, an award-winning site for planning family vacations.