5 of the Best Resorts for Multigenerational Family Vacations

Dorado Beach is one of the most exclusive oceanfront resorts on Puerto Rico’s northern coastline. Upon arrival, guests are greeted by a personal butler who handles check-in and escorts everyone to their accommodations. The resort itself stretches across acres of golden, sandy beaches, golf courses, and a five-acre spa sanctuary.

Rooms and private residences look out over the ocean or the resort’s lush grounds, with enough space and layout options to handle different family configurations. Grandparents can have their own quiet retreat while parents and kids settle into a connecting room or suite nearby.

“Puerto Rico is one of the easiest tropical trips you can plan for a multigenerational family,” Susie says. “You skip the passport coordination entirely, which sounds like a small thing until you’ve tried to wrangle paperwork for three generations at once.” She often points families toward Dorado Beach when grandparents are joining the trip for the first time in years, since the no-passport factor removes a layer of stress before anyone has even packed a bag.

The Four Seasons Peninsula Papagayo infuses every corner of the property with tropical vibes. Tree-house-style villas sit among the canopy, while suites and guest rooms feature private pools and airy outdoor spaces with panoramic views of the coast. Two pools and two beaches sit within walking distance of one another, giving families room to spread out without losing the sense of being together.

“Costa Rica is one of those places where you don’t have to choose between adventure and comfort,” Susie notes. “You can spend the morning ziplining or learning to surf and the afternoon in a robe at the spa, and the resort makes both feel equally easy.”

The Fairmont Kea Lani is Hawaii’s only all-suite and villa oceanfront resort. Every accommodation comes with spaces to come together and room to spread out, which all multigenerational family vacations can use. The grounds open directly onto the beach and the overall property is quiet, especially compared to other resorts on the island. Grandparents can retreat to their own space after a long day, parents have room to breathe once the kids are asleep, and the family can still gather in a common area without anyone feeling on top of each other. For larger families traveling together, the villas have full kitchens and enough square footage to function comfortably as a home base for the duration of the trip.

“When you’re traveling with multiple family members of varying ages, having the extra room to spread out at the end of the day helps keep everyone happy,” Susie says.

The Four Seasons Maui has undergone a complete transformation and now features refreshed accommodations, elevated pool and beach amenities, new dining concepts, and a redesigned spa and wellness center. Steps away from Wailea Beach, the resort has ocean-view guest rooms and residential-style suites.

“You can experience the best of Hawaii right at the Four Seasons Maui,” Susie says. “There’s a ton of things to do right at the resort, but you can also book excursions and activities right through the resort, which is convenient for larger groups.”

The Grand Hyatt Kauai & Spa perfectly combines luxury and accessibility. Rooms and suites look out over verdant gardens, the sparkling beach, or the lush mountainside, each with a private patio or lanai. ADA-compliant rooms feature wider entryways with at least 32 inches of clear width and lowered shelving, light switches, and peepholes for easier reach, alongside mobility-friendly bathrooms designed with real use in mind.

“This resort is one of the most accessible I’ve seen,” Susie says. “Not every resort has pool lifts and waterslide ramps. If you have loved ones with accessibility needs, The Grand Hyatt has them covered; your loved one will get to be a part of the fun with the whole family, and that’s priceless.”