Over the end-of-year holidays, the best group travel ideas usually start with a simple wish: get everyone somewhere beautiful, warm, and private, and don’t let the trip become a production.
For 2026 festive-season travel, we’re talking the sweet spot of Thanksgiving to New Year’s, Costa Rica is already leading the conversation. According to Rental Escapes booking data, Costa Rica ranks first for luxury holiday villa demand, ahead of several major Caribbean destinations. TravelPulse points to the same larger pattern: affluent families and groups are looking to spacious private villas in warm-weather destinations, with privacy, personalization, and room for everyone under one roof driving the shift.
This tells us something important about the new holiday travel: You’re not looking for a pre-packaged all-inclusive resort, but you do want the ease. You want luxury services, but not at the expense of a vacation home’s space and privacy. And you’re looking for a Costa Rica villa for rent that can hold your group, your meals, your slow mornings, your big plans, and even all your small rituals that make a holiday feel like yours.
That’s where Hacienda Pinilla begins to shine. A 4,500-acre private coastal community with beaches, golf, trails, tennis, pickleball, surf, a luxury Beach Club, restaurants, wellness options, and enough breathing room that you can all settle in, Hacienda Pinilla changes your holiday rhythm, and by that, we mean for the better.
Whether it’s Thanksgiving, Christmas, Hanukkah, Kwanzaa, New Year’s, or anywhere in the whole festive stretch from late November into early January, you have your own traditions. The food. The family gathering. The table. The drinks. The once-a-year dishes. The people you don’t always get to enjoy in one place. These are the beautiful parts of the holiday. But they also come with work, and often, that work lands on the same one or two people every year.
Until this year. This year, let us do the heavy lifting.
Keep the Beloved Holiday, Lose the Dreaded Labor
Part of what makes the holidays something we look forward to is tradition. It’s the meals we look forward to every year. It’s the way everyone gathers together. It’s the twinkling lights. The cozy time together, often with laughter lasting long into the night. It’s special traditions, the things you usually enjoy only once a year.
But if you’re the planner, you also know the other side of that beauty. The grocery lists. The airport pickups. The extra beds (and laundry). The last-minute store run. The dishes before the dishes. The dishes after the dishes. The quiet calculation of who eats what, who doesn’t eat what, who takes their coffee black vs. who needs nondairy milk, who’ll want an early dinner, who’s allergic to what ingredients, and how many times one person can reasonably wipe down the kitchen counters before calling it a holiday.
Here’s the real secret: At Luxury Villas Pinilla, we don’t ask you to give up the traditions. We just give you a way to enjoy them without shouldering every piece of the labor yourself.
That starts before you even arrive. We’ll pre-stock your kitchen with the things your group actually wants: breakfast basics, favorite snacks, drinks, fruit, coffee, wine, charcuterie ingredients, holiday treats, or the little comforts that make you feel at home away from home. Instead of landing, collecting luggage, finding the villa, and immediately wondering who’s going to the grocery store, you can open the door and just begin.
From there, the right home makes your holiday even easier. Several of our villas include Elite Service, with private in-home staff, daily housekeeping, laundry, breakfast preparation, snacks, light bites, and drinks. (You provide the ingredients.) That means the morning begins with coffee you didn’t have to brew and breakfast you didn’t have to make (or clean up, for that matter). Towels are always fresh. Laundry isn’t your part-time holiday hustle. And someone else is keeping the whole holiday machine running.
And then there’s the holiday meal itself. If you want a traditional holiday dinner, we can help arrange private chef services for turkey, ham, familiar sides, or the dishes your family waits for all year. If you want the holiday to take on a Costa Rican rhythm, it might include pierna de cerdo (pork leg), Costa Rican tamales, arroz con pollo, ensalada rusa(beet-and-potato salad), rompope (eggnog), tres leches, or a table built around local seafood and tropical ingredients. And hey, if your group wants Italian, international fusion, a lighter coastal dinner, or something entirely your own, that’s part of the fun of switching up your holiday plans.
It’s all about choice. You don’t have to abandon tradition, but you do get to decide which traditions come with you, which ones can rest for a year, and which new ones might begin right here in Hacienda Pinilla.
Why Hacienda Pinilla Makes Sense for Holiday Travel
Pictured: Casa Suerte
Hacienda Pinilla achieves that perfect holiday sweet spot: plenty to do, space to keep your group traditions close, and enough room to spread out when everyone needs a little breathing room.
It’s a very different proposition from an all-inclusive resort. Here, you’re not signing up for a schedule, a buffet line, or a vacation where every day starts to look the same by day three. Instead, you’re choosing a private, gated coastal community where almost everything you need and want is a short walk, bike ride, or golf cart ride away. And you’re choosing a private villa that can be shaped around your group, whether that means an ocean view, a private pool, ensuite bedrooms for everyone, more than one kitchen, or a table that can hold every single person and the way you like to celebrate.
Around that home, you have the rare convenience of a destination conceived to satisfy almost any travel dream. Hacienda Pinilla spans 4,500 acres, so there’s space to do things together and separately without turning the day into a negotiation. Golfers can head to the course. Tennis and pickleball players can get in a morning match. Beach people can choose Playa Avellanas, Playa Langosta, or Playa Mansita. Surfers can watch the swell. Hikers and mountain bikers can take to the trails. Someone can book a spa treatment or linger at the Beach Club, while someone else stays happily behind at the villa with coffee, a book, and absolutely no interest in checking off a single to-do box.
Never is Hacienda Pinilla’s flexibility more wonderfully on display than when you’re traveling with a mixed group. Families with children, multigenerational families with grandparents, couples traveling together, golfers, wellness travelers, and friend groups don’t always want to do the same thing all day, every day. You may not even want the same version of a morning. With Luxury Villas Pinilla, that’s finally fine. There’s baked-in choice here, and that’s one of the group travel ideas that makes for a more harmonious holiday trip.
Group Travel Ideas for the Hours You’re Not Spending in the Kitchen
This is where the holiday starts getting really fun.
Think about the hours you’d normally spend prepping, cooking, hosting, laundering, cleaning, making yet another emergency run to the store, or keeping everyone entertained. At home, when you’re the host (and sometimes when you’re not), that’s just part of the holiday rhythm. At Hacienda Pinilla, those hours become part of your vacation.
While someone else is preparing breakfast, you can be walking the beach. While a private chef is beginning to prep your holiday meal, you could be at the golf course, in the pool, out on the trails, or sipping something cold and colorful at the Beach Club. While housekeeping resets the villa, you can be doing almost anything other than laundry. And after enough years of hosting, that alone may qualify as a holiday miracle.
Hacienda Pinilla’s resort amenities are always here, all around you. But if your group travel ideas are the kind to go bigger, we can help arrange that, too: sportfishing, ATV tours, horseback riding, catamaran sailing, surf lessons, yoga, spa services, or even a helicopter tour of the coast. (And if you have little travelers with you, babysitting can make all the difference when the rest of the group heads out for something a little ambitious.)
Picture it. Really picture it: Instead of spending a holiday morning washing, chopping, prepping, cooking, sweating, and maybe even burning yourself for good measure, you could be horseback riding down one of Hacienda Pinilla’s spectacular beaches… and that’s why Costa Rica tops the list of group travel ideas this holiday season.
Where to Stay: A Costa Rica Villa for Rent Over the Holidays
Look first to villas with private staff and Elite Service included, because that’s where the promise of a hands-off, easy holiday really comes together. These homes give your group the space, privacy, gathering areas, and daily support to keep the celebration close, without asking you to carry every detail yourself.
Casa Kailua
7 Beds | 5 Baths | 14 to 18 Guests
Set within Reserva de Golf, one of Hacienda Pinilla’s most exclusive communities, Casa Kailua is an easy fit for holiday groups that want a brand-new home, generous indoor-outdoor space, and built-in support that lets everyone relax sooner.
The villa’s two-level layout gives your group room to spread out, while a large pool and spacious outdoor living areacreate the natural gathering point for slow mornings, post-beach afternoons, cocktails, snacks, and the kind of long holiday evening that doesn’t need much planning. It’s also especially well placed for groups who want to be near the beach and close to Hacienda Pinilla’s larger rhythm, from golf and tennis to yoga, surf, horseback riding, the Beach Club, and the trails.
Casa Kailua also brings the service layer this kind of trip needs. With Elite Service Standard included Monday through Saturday, your stay includes daily housekeeping, laundry, breakfast preparation, cocktails and snacks (until 2:00 p.m.), as well as a personal concierge. You provide the groceries, or we can help pre-stock the kitchen before you arrive, so the house is ready with the breakfast staples, drinks, holiday treats, charcuterie ingredients, and favorite snacks that make the first day easier.
Casa Suerte
6 Beds | 5 Baths | 10 to 14 Guests
Also set within Reserva de Golf, Casa Suerte is ideal if you want privacy, easy movement, and a layout that easily accommodates several adults. The home includes three Master Suites with direct access to the pool area, which makes it especially strong for couples traveling together, multigenerational families, or friend groups where no one wants to feel like they draw the short straw.
The pool area is the natural center of the home, giving everyone a place to gather between beach time, golf, holiday meals, and slow afternoons at the villa. A six-seater golf cart is included in your reservation, making it even easier to move between the villa, the Beach Club, the golf course, the trails, the courts, and the beach without turning every outing into a production.
Casa Suerte also includes Elite Service Standard Monday through Saturday, with daily housekeeping, laundry, breakfast preparation, cocktails and snacks until 2:00 p.m.), as well as a personal concierge. Add in yoga mats and accessories, easy access to Hacienda Pinilla’s outdoor amenities, and a setting well suited to intimate celebrations, and it becomes a strong choice for groups who want the holiday to feel generous, relaxed, and thoughtfully supported from the start.
Let’s Plan the Holiday You Actually Want
Tell us who’s coming, what you’re celebrating, and what you’d love to hand off this year.
We’ll help you choose the right Costa Rica villa for rent, pre-stock the kitchen, arrange private chef services, coordinate transportation, reserve golf carts, book tee times, plan surf lessons, organize babysitting, and build in the group travel ideas that fit your people best. Maybe that means a traditional holiday dinner, a Costa Rican Christmas meal, a New Year’s celebration by the pool, a few big adventure days, or a week where everyone finally gets to slow down
However you want the holiday to look, we’ll help make it easier from the moment you arrive. Get in touch, and let’s start planning.