5 There is a particular kind of magic — and a particular kind of logistical challenge — to a holiday shared by three generations. Grandparents who want shade and a good book. Parents who want a moment of peace. Teenagers who want Wi-Fi and independence. Young children who want a pool, a slide, a dog, and dinner at five o’clock sharp. I’ve been helping families navigate this for over a decade. The good news? When you get it right, a multigenerational villa holiday is one of the most joyful experiences a family can share. The trick is knowing exactly what to look for in the property. Here is my honest guide. 1. Space — Both Together and Apart The single biggest mistake families make is booking a villa that only works when everyone is in the same room. What you actually need is a property that allows people to be together and separate, fluidly, throughout the day. I look for villas with multiple living spaces — a main salon, a secondary sitting room or library, a shaded outdoor terrace as well as a sunny one. Grandparents may want to rest after lunch while the children are still splashing in the pool. Teenagers need somewhere to disappear to in the evenings. Parents need a corner of the terrace that is entirely their own at nine o’clock at night. Separate bedroom wings are also worth seeking out. There is a reason that the most popular multigenerational villas in our collection tend to be those where different family units have their own section of the house. 2. Accessibility — More Important Than You Might Think If your group includes older grandparents or anyone with limited mobility, the question of accessibility can make or break the holiday. Stairs, uneven stone floors, narrow doorways, hillside settings — these can all turn a beautiful villa into a difficult stay. I always ask clients directly: is there anyone in your group who has difficulty with stairs? And I encourage you to be honest in your answer. A good villa specialist — and that’s why you’re talking to us rather than scrolling a booking site — will find you the right property. Ground-floor bedrooms, walk-in pools, and step-free outdoor areas are features we can filter for. Ask us. 3. The Pool — It’s Not Just for the Children Every generation uses the pool, but they use it differently. Children want depth and space to play. Grandparents want a shallow shelf or easy steps for getting in. Parents want a comfortable lounger at a safe sightline. If your group includes very young children, a shallow paddling area or a pool with a built-in ledge is worth prioritising. Several of our Italian and Greek properties have stunning infinity pools that are breathtaking to look at — but a sharp drop from the edge is not what you want with a three-year-old. 4. The Kitchen — Or Better, a Chef With a multigenerational group, mealtimes can become the most stressful part of the day. Different dietary needs, different meal times, the physical and emotional labour of cooking for twelve people on holiday. My strongest recommendation for large family groups is a villa with a private chef — at least for the evenings. It changes the dynamic entirely. Dinner becomes an occasion rather than a chore. And everyone, from the grandparents to the smallest grandchild, gets fed something they actually want to eat. Several of the properties in our family collection include chef services as part of the package, or we can arrange this for you through our concierge. 5. Location — Think Carefully About Transfers A remote hilltop villa sounds romantic until you’ve made four separate car journeys to the nearest restaurant, pharmacy, beach, and supermarket in a single day. With a multigenerational group, convenience matters more than it does for a couple or a group of friends. Look for villas within a reasonable drive (or walk) of a village or town — somewhere with a café, a pharmacy, and ideally a beach or a viewpoint that rewards the trip. In Puglia, for example, the properties around Ostuni, Alberobello, or the coast near Torre Canne tend to work well for mixed-age groups. In Tuscany, the area around Montalcino or Cortona offers accessible villages alongside dramatic countryside. In Greece, the islands with more infrastructure — Corfu, Zakynthos, Crete — tend to work better for families with elderly grandparents than the more remote Cyclades. My Top Destinations for Multigenerational Families Based on years of placing families in the right homes, these are the destinations I recommend most often: Puglia, Italy — Gentle terrain, accessible beaches, extraordinary food, family-friendly culture Tuscany, Italy — Iconic landscapes, wonderful villages, strong villa infrastructure for large groups Corfu, Greece — Lush, less arid than many Greek islands, accessible and with beautiful beaches Crete, Greece — Size means variety: you can find coast, mountains, culture, and excellent medical facilities Algarve, Portugal — Excellent flight connections from the UK, reliable sunshine, family beaches The most important thing I’ve learned after years of doing this: don’t try to find a villa that suits everyone equally. Find one that has enough space and variety that different members of the group can each find their own version of perfect. The rest takes care of itself. Planning a multigenerational holiday? Let Paola take the guesswork out of it. Tell me who’s coming — ages, mobility, what the kids love, what the grandparents need — and I’ll come back to you with a shortlist that actually works. → Email Paola: paola@passepartout-homes.com ✉Or request a callback at passepartout-homes.com Browse family villas: passepartout-homes.com/collection/family Browse large-group villas: passepartout-homes.com/collection/xxl family holidaysMultigenerational Travel