Plan the ultimate multigenerational getaway at these five private escapes, where families can reconnect, explore and experience unforgettable luxury together.
From private islands to snow-dusted mountain homes, today’s ultraluxury villas offer far more than beautiful spaces. They create the backdrop for memories shared across generations. These five exceptional estates blend privacy, adventure and thoughtful design to bring families together in spectacular settings.
KOKOMO PRIVATE ISLAND, FIJI
Why We Love It: With five private residences of up to six bedrooms, each with a dedicated nanny, Kokomo is a barefoot-luxury paradise where vibrant reefs, warm hospitality and polished service combine to create a stress-free haven for all ages.
Must-Try Family Outing: Explore the 62-mile-long Great Astrolabe Reef on a snorkeling or diving excursion, then settle in for a secluded sandbank picnic and a dose of pure tropical bliss.
Over-the-Top Amenity: The five-bedroom Astrolabe residence boasts a private garden, an expansive outdoor entertaining space and the island’s largest private pool.
BLACKBERRY MOUNTAIN, TENNESSEE
Why We Love It: Tucked into the Smoky Mountain foothills near Walland, Blackberry Mountain offers standalone homes with multiple bedrooms, so grandparents, parents and kids each get their own space while sharing one extraordinary base. Fireside mornings, forest trails and long communal dinners give every generation room to roam and reasons to gather.
Essential Outing: Spend a day hiking the property’s wooded ridges, then regroup for a chef-led tasting built around regional ingredients. Booking a multi-home estate like this can be the hardest part of planning a US trip, since the best places rarely sit on a single platform. Services such as Rove help families find and secure curated luxury stays across the US without the usual scramble.
Over-the-Top Amenity: Private spa treatments and a wellness program let the adults unwind while younger guests join guided outdoor adventures tailored to their pace.
TRISARA, THAILAND
Why We Love It: Boasting private residences with dedicated staff and up to 10 bedrooms, Trisara is a serene oceanfront sanctuary in Phuket where families celebrate milestones amid fragrant gardens, soft waves and timeless Thai elegance.
Essential Outing: A private long-tail boat adventure through hidden coves and limestone cliffs makes the perfect setting for unforgettable family photos.
Over-the-Top Amenity: At PRU, Phuket’s only Michelin-starred restaurant, families can reserve a privately curated tasting journey using ingredients handpicked from the property’s own organic farm.
FAWN BLUFF, BRITISH COLUMBIA
Why We Love It: Formerly owned by Michelle Pfeiffer and David E. Kelley and debuting as a lodge on June 1, Fawn Bluff is a six-bedroom coastal estate nestled on 340 acres against the Great Bear Rainforest, blending wild natural beauty with refined comfort. Families share sunsets on the shore, spot orcas offshore and gather for meals inspired by regional flavors.
Essential Outing: Set off on a guided wildlife excursion to see eagles, whales and bears in their natural domain, followed by paddleboarding on the serene Leask Lake.
Over-the-Top Amenity: A separate Lake Cabin on Leask Lake offers a secluded getaway spot for a romantic evening.
ONE&ONLY MOONLIGHT BASIN, MONTANA
Why We Love It: At this stylish property, generations can reconnect amid the breathtaking peaks and wild forests of Big Sky. The alpine-chic haven blends rugged scenery with luxurious private homes of up to six bedrooms, where grandparents can luxuriate by the fire while the kids plot tomorrow’s adventure.
Essential Outing: Venture out for a day on the snowcapped slopes tailored to your family’s pace, from gentle glades for beginners to thrilling runs for the more adventurous, followed by spa time and family dinners at pro-snowboarder-turned-celeb-chef Akira Back’s buzzy restaurant.
Over-the-Top Amenity: The spa’s Alpine Nourishment Ritual delivers four individual treatments to renew the body from head to toe over nearly five luscious hours.
Making the Trip Last Beyond the Stay
The appeal of these retreats isn’t only the setting. It’s the rare stretch of unhurried time that gets several generations under one roof, away from the routines that usually keep them scattered. The best of them are built for exactly that, with separate residences that give everyone privacy, shared spaces that pull the group back together at mealtimes, and staff who handle the logistics so no single person spends the week playing trip coordinator. That balance of togetherness and breathing room is what separates a genuine multigenerational escape from a regular family vacation.
A getaway like these is often a gift in itself, especially when grown children plan it for parents or grandparents. If you’re giving one of these escapes as a present, consider pairing it with something that captures the stories the trip stirs up. A guided memory book such as Remento prompts parents and grandparents to record their recollections, turning a week together into a keepsake the whole family keeps long after everyone heads home. The conversations that surface over a slow dinner or a long drive between activities are often the ones worth holding onto, and they tend to slip away if nobody writes them down.
