At some point, traveling with your parents stops sounding like something you used to do and starts sounding like something you’re lucky you still can do.
Maybe that realization arrives slowly. Your parents are older than they were the last time you all took a proper trip together. Your children are growing fast, somehow faster every year. The grandparents are still active, still game, still happy to get on a plane for the right reason, but you’re aware, in a way you may not have been ten years ago, that this window’s precious.
That’s part of why multigenerational family vacations are having a moment. According to the 2025 U.S. Family Travel Survey from the Family Travel Association and NYU SPS, 92% of parents say they’re likely or very likely to travel with their children in the next 12 months, and multigenerational trips are now a major part of that picture, with 71% of grandparents having taken one recently and 57% planning one in the future.
Maybe you’re ready to join them. So, let’s talk about how to make it happen.
Why Families Are Making Time for Multigenerational Travel Now
Pictured: Casa Kailua
It makes sense. Families are spread across cities, countries, school calendars, work calendars, and entire lives that don’t overlap as easily as anyone would like. A long weekend isn’t always enough anymore. Dinner during a holiday visit is lovely, but it’s not the same as several days together, with nowhere better to be and no one rushing off to an obligation.
For families with the means to choose well, the question’s become less “Should we take the trip?” and more “Where can we go that’ll actually give everyone what they need?” Because bringing three generations together is a beautiful idea, but making it work well, making it so that grandparents, adult children, and grandchildren all feel comfortable, engaged, rested, and happy to be there, asks for the right setting on several fronts.
That’s where Hacienda Pinilla, and our Costa Rica villas, enter the conversation. Costa Rica gives you the adventure, the wildlife, the ocean, the warmth, and the sense that everyone’s stepped out of ordinary life for a while. Hacienda Pinilla gives that experience privacy, security, space, and range. And the right villa gives your family the architecture for something rarer than a vacation that looks good on paper: a trip that actually works for the people taking it.
The New Luxury Is Time With People You Love, Doing Things You Love
For many families, travel has become much more than a pleasant way to spend a school break. It’s often one of the most meaningful ways to use time, resources, and generosity while everyone’s here to enjoy the gift together.
That’s especially true for grandparents. Many are no longer thinking only about what they’ll leave behind one day. They’re thinking about what they can experience now, with the people they love sitting across the dinner table, walking the beach, learning to surf, watching the youngest grandchildren fall in love with the pool, or seeing their adult children relax in a way that real life rarely allows.
RBC Wealth Management describes multigenerational travel as a way for families to build legacy through shared experience, which feels especially true for grandparents who want to enjoy their generosity while everyone’s still here to experience it together.
A family trip can become a kind of living inheritance, not in the legal sense, but in the human one. It’s wealth translated into time. Into stories. Into the memory of a grandfather watching his granddaughter ride a horse for the first time, of a grandchild building sandcastles with his grandparents, or three generations gathering for dinner after a day split between golf, beach, naps, and something a little more adventurous than anyone expected.
The key, though, is that the trip can’t rely on togetherness alone. Time with people you love is the luxury, yes, but so is doing things you love while you’re together. A grandmother who wants quiet mornings shouldn’t have to spend every day on a high-energy excursion. A teenager shouldn’t be expected to find meaning in long lunches alone. Parents who’ve spent months organizing the trip shouldn’t arrive only to become the default logistics team.
The most successful multigenerational family vacations leave room for all of it: shared adventure, private downtime, family meals, separate mornings, big moments, small rituals, and the lovely relief of watching everyone find their own pace without drifting too far from each other. That’s where Costa Rica, and especially Hacienda Pinilla, becomes such a compelling choice.
Multigenerational Family Vacations Still Need the Right Architecture
Pictured: Casa Suerte
Multigenerational travel is special, but it’s not effortless by default.
Bringing grandparents, parents, adult siblings, cousins, teenagers, and young children into one vacation means bringing several households into the same rhythm, and everyone arrives with their own needs. Some people wake early. Some need quiet. Some want every day to include an activity. Some want the pool to be the activity. Someone may need a ground-floor bedroom. Someone else may be dreaming about one long dinner where nobody checks the time.
A successful multigenerational trip needs the right architecture, both literally and emotionally. Travel researchers and family-travel experts often talk about the balance between “own time” and “family time,” and anyone who’s taken one of these trips understands exactly why. The goal is to create enough shared experience that the trip becomes part of the family story, while still giving each generation enough space to enjoy the vacation in a way that feels natural to them.
That’s where a private luxury villa begins to outperform even the most upscale hotel. A hotel can give everyone rooms, but a villa can give everyone a shared life for the week. The kitchen, the pool, the terrace, the long table, the living room, the morning coffee spot, these are the places where the trip actually happens. They’re also the places where the practical realities of family travel become easier: nap time, snack time, a slow morning, an early bedtime, a private chef dinner, a quiet hour, a last swim before bed.
Why Hacienda Pinilla Works So Well for Multigenerational Family Vacations
Hacienda Pinilla gives your family that larger structure around the villa. Set across 4,500 acres of coastline, tropical dry forest, ranch land, and residential enclaves, it offers the privacy and security of a gated community with the range of a full Costa Rica family adventure close at hand. You’re not choosing between comfort and experience. You’re choosing a place where both can live inside the same trip.
The beauty of Hacienda Pinilla is that the days can be as shared or as separate as the family needs them to be. Everyone can head out together for a sunset catamaran, a zipline tour, sportfishing, snorkeling, or a national park day. Then, on another morning, the trip can split into smaller pieces without becoming complicated. Someone plays golf. Someone goes to the Beach Club. Someone takes the kids to the pool. Someone walks Playa Avellanas. Someone stays at the villa with coffee and a book, which may be the wisest plan of all.
Inside the community, the options already cover a remarkable amount of ground:
Three Beaches, Three Different Speeds
Playa Avellanas brings surf, sand, Beach Club energy, and sunset. Playa Langosta is wilder and more scenic, with tide pools, tree-lined shoreline, and a quieter coastal edge. Playa Mansita offers a calmer pocket near the JW Marriott, especially lovely at low tide. Three generations rarely want the exact same beach day, and here, they don’t have to.
The Beach Club as a Natural Meeting Point
The Hacienda Pinilla Beach Club gives everyone a place to overlap without forcing everyone into the same activity. There’s the oceanfront pool, open-air restaurant, Tiki Bar, spa rooms, and Pacific-facing fitness center. One person can swim. Someone else can order lunch. Someone can book a treatment. Someone can work out with the ocean in view. It’s a beach day with options built in
Golf, Trails, Courts, Horses, and Surf
For active families, Hacienda Pinilla keeps movement close: a championship 18-hole golf course, tennis and pickleball, hiking and biking trails, horseback riding, and surf at Avellanas and Langosta. For families that want bigger outings, your concierge can also help arrange the larger Guanacaste experiences that make Costa Rica so memorable, from catamaran sailing and sportfishing to ziplining, wildlife tours, snorkeling, scuba, and national parks.
That range is why Hacienda Pinilla works so well for multigenerational family vacations: It gives your family a private home base, then surrounds you with enough variety that grandparents, parents, children, and cousins can each find their own version of the trip without losing the pleasure of being together.
The Right Villa Makes the Whole Trip Easier
Of course, even the best destination needs the right home. For multigenerational family vacations in Costa Rica, the villa does a lot of quiet work.
That’s why choosing well is so important. Some families need separate casitas or guest suites. Some need bunk rooms, toys, or a shallow pool area for younger children. Some need a gym, a sauna, a movie room, a chef-ready kitchen, or enough outdoor living space that twenty people can spend an afternoon together without feeling crowded.
The right villa isn’t simply the one with the longest amenity list; it’s the one that really “gets” how your family actually travels. It makes room for shared meals and private mornings, big celebrations and early bedtimes, the child who needs a nap and the grandparent who needs a quiet hour, the cousin who wants to stay in the pool until sunset and the uncle who’s already booked tomorrow’s tee time.
That’s the luxury of a villa inside Hacienda Pinilla. Your family has the privacy of a home, the range of a gated coastal community, and the support of a concierge team that knows how to make the pieces fit together.
Where to Stay
The right home gives a multigenerational trip its shape. It’s where everyone lands after the airport, where the children claim the pool, where grandparents find their morning coffee spot, where long dinners stretch later than planned, and where the family begins to feel, for a few days, like it all lives under one roof again.
The following villas are especially well suited to families who want space, privacy, comfort, and the kind of indoor-outdoor living that makes a Costa Rica family adventure feel both exciting and easy.
Casa Kailua
7 Beds | 5 Baths | 18 Guests
Welcome to Casa Kailua, an exquisite escape in the exclusive Reserva de Golf community of Hacienda Pinilla. This brand-new luxury home invites you to indulge in a seamless blend of modern elegance and five-star hospitality, offering the ultimate setting for an unforgettable getaway.
Designed for expansive indoor-outdoor living, Casa Kailua boasts two spacious levels, a private pool with a sun-drenched lounge area, and an atmosphere of pure tranquility. And because time together shouldn’t be about cleaning and the constant parade of daily food preparations, your stay includes daily housekeeping, a dedicated concierge, and staff-prepared breakfast, snacks, and drinks, ensuring every detail is effortlessly handled.
As a guest, you’ll enjoy exclusive access to Hacienda Pinilla’s world-class Beach Club, as well as tennis courts, an 18-hole golf course, horseback riding, and miles of scenic trails. Whether you’re seeking adventure or relaxation, Casa Kailua delivers the best of Costa Rica’s luxury lifestyle. Your escape awaits!
Casa Suerte
6 Beds | 5 Baths | 10 to 14 Guests
Just minutes from pristine beaches and world-class golf, Casa Suerte is a sophisticated retreat, blending modern comfort with tropical tranquility. Designed for seamless indoor-outdoor living, this stunning villa boasts a private pool, spacious living areas, and a fully equipped gourmet kitchen.
And then, there’s its setting: Located within Hacienda Pinilla, an elite gated community spanning 4,500 acres, your stay includes access to a championship golf course, tennis courts, hiking and biking trails, and the Hacienda Pinilla Beach Club, featuring an oceanfront infinity pool, open-air restaurant, fitness center, and direct access to Playa Avellanas – a haven for sun-seekers and surfers alike.
Of course, you’re here for more than the setting, and in that, Casa Suerte delivers. Savor sun-drenched days on the terrace, cool off in your private pool, and retreat to inviting bedrooms (four with an ensuite bath). Plus, enjoy Elite Service, including daily housekeeping, to elevate your stay. Welcome to the good life!
Ready to Plan a Multigenerational Family Vacation That Actually Works?
When you book with Luxury Villas Hacienda Pinilla, every stay includes complimentary concierge service, and that support begins with a simple idea: we listen first, plan second.
Once you reserve your villa, we’ll get to know your family, who’s coming, how old the children are, what the grandparents need, how much structure you want, and what everyone pictures when they imagine the trip going beautifully. From there, we can help with the details that make multigenerational family vacations feel easier: airport transportation, golf cart rental, groceries, private chef services, tee times, surf lessons, horseback riding, spa appointments, restaurant recommendations, catamaran sailing, sportfishing, ziplining, and a full Costa Rica family adventure if that’s what your family wants.
The goal isn’t to fit three generations into one rigid itinerary. It’s to shape a stay where everyone has room to enjoy the family, the destination, and the time you’ve chosen to spend together.
Get in touch, and let’s start planning.