Family reunion-worthy homes you’ll never want to leave

When it comes to family reunions, the setting matters. You need space for everyone, comfort across generations, and a layout that brings people together—without sacrificing style.

These handpicked retreats are perfect for your next big gathering—designed to spark connection, create memories, and maybe even start a few new traditions.

Stunning oceanfront vacation home in Chatham, MA

Fox Hill – Chatham, MAThis expansive Cape Cod estate was designed with multigenerational gatherings in mind. With five bedrooms and 10 bathrooms spread across three levels, and a private guest suite with its own full kitchen and living room, every family member has space to relax in comfort. Open-concept living areas invite cozy conversation, while the expansive deck sets the stage for catching up over cocktails or morning coffee. With elevator access to every floor and a private boat dock just steps away, this home is welcoming, spacious, and appeals to everyone.

Escondido – Malibu, CAInspired by the Greek Isles, this private, gated Malibu estate spans two lush acres lined with palms, olive, and fruit trees. With seven bedrooms and 11 bathrooms, including a remodeled guest house perfect for teens seeking a little independence, there’s room for the whole family to spread out in style. Inside, a home theater, wine cellar, and game room provide entertainment for all ages, while the outdoor sparkling pool, volleyball court, and open-air kitchen offer sun-soaked days and dinners under the stars. There’s even a home gym and cozy bunks for the kids. Spacious, stunning, and thoughtfully designed, this is California family living at its most luxurious.

A stunning snowy aerial view at 425 Wood Road58, Aspen, CO 81611, capturing the essence of elevated living and the breathtaking landscapes that complement the Snowmass Balloon Festival.

Alpine Ridge – Snowmass Village, COHost your next family gathering here, and you’ll set the bar sky-high. With true ski-in/ski-out access and direct mountain entry, this spacious Snowmass retreat is designed for life’s most memorable moments on and off the slopes. Panoramic alpine views greet you at every turn, while generous living spaces provide room for everyone: cousins can spread out, grandparents can unwind by the fire, and the whole crew can gather for après-ski meals and late-night laughs. This year-round mountain home brings the entire family together without ever feeling crowded.

back of house featuring a swimming pool with hot tub and a lawn at 2610 Atlas Peak Rd, Napa, CA 94558, illustrating the appeal of outdoor amenities in second homes as seasons change

Arterra – Napa, CATucked away in a 31-acre private valley in Napa, this secluded wine country estate is a superb setting for family get-togethers. The modern yet timeless main home is bathed in natural light, with a separate guest house offering extra space and privacy for extended family. Kids can splash in the pool while adults play bocce or relax on the shaded patio. Come evening, gather around the firepit for s’mores and stories, with glasses of local Cabernet for the grown-ups and sparkling cider for the younger crew. An outdoor kitchen invites leisurely al fresco meals, surrounded by nature and good company. And when you’re ready to explore, Downtown Napa’s world-class wineries and restaurants are just a short drive away. This is a home that brings every generation together comfortably, and beautifully.

The Oasis – Palm Springs, CASpread out, stay active, and make lasting memories at this dreamy desert compound, designed for indoor-outdoor living and perfect for large family gatherings. From pool games and friendly tennis matches to putting green challenges and starlit trivia showdowns, this resort-style retreat is an excellent venue for a playful family Olympics. Open-concept living spaces and a chic bar make it easy to host, while the grand veranda invites everyone to gather for sunset cocktails, roasted marshmallows, and stories around the twin fire pits. This jaw-dropping estate might just become the family’s favorite reunion spot.

Windmill Palms – Marco Island, FLThis private waterfront retreat is an exceptional venue to reconnect with loved ones near and far. The open-concept floorplan and ample outdoor space encourage lively conversation and connection. Spend sunny dats on the covered lanai, grilling lunch and lounging poolside. When adventure calls, take advantage of direct bay access and hop on a paddleboard or kayak to explore the California coast. From toddlers to grandparents, there’s something here for everyone. And with pristine beaches, top-rated restaurants, and world-class golf just minutes away, this timeless escape is more than a vacation home; it’s where family memories are made. Pacaso makes it easy to find a home that checks every box for hosting the ultimate family gathering. Our co-owned homes are thoughtfully designed, beautifully furnished, and expertly maintained, so you can skip the stress and savor the moments that matter.

Family reunion-worthy homes you’ll never want to leave

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