When the gate closes behind you, you’ll know the trip has finally begun.
Not at the airport. Not on the drive in. Right there, when you finally see the Hacienda Pinilla sign, the guard waves you through, and the pace of the outside world begins to loosen its grip. There’s still movement, of course, the last turn toward the villa, the bags coming out of the car, someone already asking where the pool is, but the mood has changed.
You’ve swapped the hotel lobby or a resort’s hectic choreography for your own private world within Hacienda Pinilla’s 4,500 acres of coastline, ranch land, forest, and carefully held quiet. And that’s exactly why more families are looking at gated communities in Costa Rica instead of traditional resorts.
Recent family travel research from the 2025 U.S. Family Travel Survey, produced by the Family Travel Association, NYU SPS, and Good Housekeeping, found that multigenerational trips are a major trend, with 71% of grandparents having recently traveled with children and grandchildren, and 57% planning a multigenerational trip in the future. What’s more, Squaremouth reports that 47% of travelers were opting for multigenerational or family trips in 2025, up 17% over 2024.
And the appeal is easy to understand, once you’ve traveled with three generations under one roof: space is no longer an indulgence. It’s the thing that makes your trip work beautifully.
When Everyone Travels Together, the House Matters
A multigenerational trip sounds simple in theory. Everyone gathers somewhere beautiful. The kids make memories with their grandparents. Parents get help, grandparents get time, and the family finally has the kind of togetherness that ordinary life rarely allows.
In practice, the logistics are less poetic. Someone wakes early. Someone needs a nap. Someone wants the pool. Someone else wants silence. Teenagers need space. Grandparents need shade. Parents need 15 minutes when no one’s asking them where the goggles are.
This is where private villas at gated communities in Costa Rica begin to make very good sense. You’re not dividing the family across hotel rooms and hoping everyone ends up on the same floor. You’re not coordinating elevator rides, breakfast windows, or who claimed which chair. You’re in one home, with room to separate and gather, and those two things matter equally.
It’s no surprise, then, that luxury villa demand is moving in the same direction: Zicasso data cited by Parents shows multigenerational groups choosing villas over hotels at a 4-to-1 ratio. That’s because the best multigenerational family vacation ideas are not always the ones with the longest activity list. Sometimes, they’re the ones that let everyone operate in parallel.
Coffee on the terrace for early risers. Pool time for the kids. A long beach walk for whoever wants movement. A shaded reading corner for whoever has earned the right to do absolutely nothing. That’s the special magic of a private, multigenerational villa.
The Privacy Families Are Actually Booking
Privacy has become one of luxury travel’s most valuable currencies, but the word can sound much colder than the reality.
At Hacienda Pinilla, privacy is warm. It’s barefoot. It’s the sound of your own group laughing around the pool without worrying about who can hear. It’s lunch happening when everyone is hungry, not when a restaurant reservation says so. It’s the freedom to spend an entire day in swimsuits, moving between kitchen, terrace, pool, and hammock with no audience at all.
This is the part that resorts struggle to deliver. They can offer service, beautiful settings, and excellent amenities, but they cannot give your family complete ownership of the day. A villa can.
And Hacienda Pinilla adds something more unusual: privacy without isolation. You can live inside your own small world, then step beyond it into a larger one whenever the mood shifts. Three beaches. The Beach Club. Golf. Tennis and pickleball. Horseback riding. Mountain biking. Surf. Restaurants. Spa access. Trails that move through forest, ranch land, and coastline.
You don’t have to choose between retreat and experience, because that choice is already built into this retreat experience.
Welcome to 4,500 Acres of Authentic Costa Rican Landscapes
Security is rarely the most glamorous part of travel writing, but for families, it changes everything. Inside our gated community, the edges of your vacation soften. The constant background vigilance lowers. Kids have more room to move. Parents relax into the day more quickly. Grandparents aren’t navigating the rush and unpredictability of a large resort property.
At Hacienda Pinilla, our gated setting works because it is paired with scale. The community does not feel compressed or overly manicured. It opens across 4,500 acres of Guanacaste landscape: tropical dry forest, reforested ranch land, rolling trails, Pacific shoreline, and long stretches of road where the scenery itself slows the car.
This is luxury in a more grounded form. Not spectacle for spectacle’s sake, but the ability to move through a beautiful, secure environment without friction. You can send one group to the golf course, another to the Beach Club, and another to the villa pool, and the day still holds together.
The World Inside Hacienda Pinilla
Hacienda Pinilla is not a resort disguised as a neighborhood; it’s a coastal community with real range, which is what makes it so useful for families traveling together.
The beaches alone offer different moods. Playa Avellanas is the icon, known for its soft sand, surf culture, and the Beach Club perched along its shore. Playa Langosta is more rugged and elemental, edged by native trees and loved for its wild beauty. Playa Mansita, near the JW Marriott, is smaller and more intimate, especially at low tide when the Pacific draws back and reveals the rock formations along the sand.
Then there is the Beach Club, one of Hacienda Pinilla’s central pleasures. Its infinity-edge pool looks toward the Pacific, with the Tiki Bar, open-air restaurant, spa rooms, and second-floor fitness center all set close to the water. You can swim, order lunch, watch the surfers, schedule a treatment, or simply sit long enough for the afternoon to rearrange itself around the ocean.
The golf course gives the community another kind of rhythm. Designed by Mike Young, the par-72 course follows the natural contours of the land across 18 holes and up to 7,200 yards. It is also an Audubon Cooperative Sanctuary, which means the surrounding wildlife and habitat are part of the experience, not decorative scenery. Golfers may come for the game, but the Pacific views, birds, deer, and movement of the landscape have a way of becoming part of the story.
For more active families, horseback riding connects directly to Guanacaste’s ranching heritage. These are not generic trail rides through a resort path. Hacienda Pinilla’s horseback routes move through forest, pasture, and beach, echoing the sabanero (cowboy) culture that still shapes the region. Mountain biking and hiking trails extend for more than 45 kilometers across coastline, cattle land, forest, and resort areas. Tennis and pickleball courts add another layer of easy morning movement. Surfing at Playa Avellanas and Playa Langosta brings the Pacific into the center of the trip.
The point is not to do everything. The point is that everything is right here.
Multigenerational Family Vacation Ideas That Don’t Require a Clipboard
The phrase multigenerational family vacation ideas usually produces a predictable list: beach day, nature tour, family dinner, maybe a boat ride. Those are all worthy and Hacienda Pinilla can deliver them beautifully. But the more valuable thing is how naturally the experience can split and reunite.
Your family might start the morning together over breakfast at the villa. By 10, the golfers have peeled off toward the course, the kids are in the pool, and someone has claimed a quiet spot under the rancho with a book that may or may not actually get read.
Lunch brings everyone back. The afternoon sends half the group to the Beach Club and the other half into nap territory. By sunset, people drift toward the terrace again, carrying stories from separate versions of the same day.
That is the hidden architecture of a successful family trip. Togetherness is not constant proximity, but rather the ability to move apart comfortably and come back together easily. Our private villas make that possible, our gated community makes it feel seamless.
Villa Encantada
10 Beds | 11 Baths | 20 to 50 Guests
Villa Encantada is built for the kind of family trip that needs scale, privacy, and a little drama. Set in the jungle and still close to the beach, this 10-bedroom estate gives large groups room to gather without compressing the experience into a single shared space. It works beautifully for multigenerational families, milestone celebrations, weddings, and special events, especially when the guest list needs room to breathe.
The outdoor areas are the heart of the property. A private pool with water volleyball turns ordinary afternoons into the kind of memory kids will retell with suspicious exaggeration. Expansive lawns and resort-like gathering spaces make room for sunset cocktails, long dinners, event setups, and slow mornings that slide happily into afternoon. With pre-approval, the estate can host events for up to 200 guests, which makes it one of the most versatile homes in our collection.
Villa Encantada also solves one of the biggest challenges of large-group travel: meals. With Elite Service and private chef support, your group can settle into a no-cooking, no-cleaning rhythm. Choose your menu, provide the groceries, or let the team help coordinate the details. Daily housekeeping keeps the home reset, while your concierge helps with everything from transportation and golf carts to activities and special requests.
Located 1.5 miles from the beach and 1.7 miles from both the Hacienda Pinilla Beach Club and JW Marriott, Villa Encantada sits close to the community’s amenities while remaining fully its own world.
Why Families Come Back to This Kind of Stay
A resort can be lovely. Many are. But once your family has experienced the ease of a private villa inside a gated community, the old model suddenly gets strangely crowded.
At Hacienda Pinilla, the day belongs to your family from the beginning. You decide when breakfast happens. You decide who goes where. You decide whether the afternoon calls for surf, golf, a spa treatment, or silence by the pool. The structure is there when you need it, and invisible when you don’t.
That is why gated communities in Costa Rica are becoming one of the most compelling answers to modern family travel. They offer security without sterility, privacy without isolation, and access without noise. They understand that a family trip is not one experience, but many overlapping ones, all happening under the same roof.
When the gate closes behind you, the outside world does not disappear completely. It simply stops running the show. And that’s the real luxury families are choosing now.
Need More Multigenerational Family Vacation Ideas?
Did you know that when you book with Luxury Villas Hacienda Pinilla, you gain access to our full concierge services?
When you book, we’ll get in touch to help you plan all the details of your stay. Our job is to get to know you, so we can help you plan the trip of your dreams. Whether you just need help arranging transportation or would like a full itinerary – everything from your airport shuttle to a full trip’s worth of activities, private chef services, and golf cart rental – we’re happy to help.
So, why wait? Get in touch and let’s get started!