Multifamily Vacation Rentals Big Enough for Your Whole Crew (And Then Some)

About a decade ago, my wife and I started spending a week in the Hamptons each June with a group of other families at a charmingly run-down collection of converted farm buildings. The place is like a little pocket of the Catskills that got lost in chichi eastern Long Island: It’s pleasingly rustic and disheveled, but the neighbors own professional sports teams and keep Serra sculptures on lawns large enough for their players to scrimmage. It’s one of those word-of-mouth rentals (I’ve been asked not to name it), passed around through the years among like-minded NYC creatives. Days have a pleasing sameness, revolving around the divine local beaches and cooking communal alfresco meals utilizing the compound’s multiple kitchens and barbecues before sitting by the fire with a glass of whatever’s being poured while the june bugs twinkle.

I dug this getaway when I was younger and childless, but as our group of friends has aged and had babies and migrated out of New York City to the suburbs or California, it has come to mean so much more—particularly now that my kids are old enough to look forward to going each summer. The pandemic took it from us last year, so it was especially sweet this summer to see my little ones reunited with friends who’d grown a head since the last time we saw them and showed up with new haircuts, new books, new lingo. And it was sweet for me, too, to have a dear chef friend tutor me on my knife skills as we worked together prepping larb and bun for the Southeast Asian-themed night or to sit up till midnight under the stars talking about late-’70s Dylan and the Brooklyn Nets with a couple of dudes. And it was sweet for all of us to come together and see that we’d all made it through this dark time in the world and know that we could keep coming together like this as our children grow taller and the lines around our eyes grow deeper.

So sweet, in fact, that a bunch of us plan to do it again soon, at a converted boys camp on Lake Pemaquid in MidCoast Maine, where we’ll once again cook and swim and sit by the fire. In my life so far, outside of the those weeks in the Hamptons, I’ve really only taken part in these kinds of big group rentals for destination weddings. But our cohort has pretty much aged out of weddings, and our lives have taken us farther and farther apart from one another, so we need weeks like these to come back together, to eat, to check up on each other. There are email threads going right now about Taos, Andros, Mallorca. Who knows where we’ll meet up next.

More amazing rentals for multifamily retreats

Camp Wandawega

Elkhorn, Wisconsin

First opened as a speakeasy two hours north of Chicago and later reopened as a resort in the ’50s, Camp Wandawega has three-bedroom lakefront cabins, rustic bunkhouses that sleep up to 24, or the modern two-bedroom Hillhouse. All include access to summer camp go-tos like fishing, canoeing, hiking, archery, and more. Cabins from $650 per night.

Scarp Ridge Lodge

Crested Butte, Colorado

Find relaxing mountain elegance behind a former saloon storefront in this six-bedroom getaway from Eleven Experience. They’ve thought of everything, from the seven-bunk dorm room for the kids to the oxygen-enriched air system to help you adjust to the nearly 9,000-foot altitude. Wind down after exploring Crested Butte’s summer hiking trails and winter slopes in the indoor saltwater pool, steam room, or rooftop hot tub. $19,900 per night based on 10 people (maximum occupancy is 14).

Eleanthi

Pirgos, Greece

Set on one of the highest points in Pirgos, just a few minutes from the beach on the Mani Peninsula and just over three hours southwest of Athens, this former 19th-century monastery turned five-bedroom vacation home split between two semidetached buildings has incredible views from its private rooftop balcony. There’s room for everyone to spread out, between the main kitchen, airy courtyard, olive garden, and multiple living areas with original stonework. From $450 per night for up to 13 guests.

La Selva Giardino del Belvedere

Montegonzi, Italy

This luxe 17th-century estate with three villas, about an hour’s drive from Florence, has something for everyone: a private saltwater pool, 45 acres of olive trees, pizza ovens (yes, more than one!), views of the Tuscan countryside from every angle, and even a stone amphitheater. Be sure to coordinate a chef-prepared dinner (or at the very least a private pasta-making lesson) during your stay. From $980 per night for up to 10 guests.

Casa Blue

Tamarindo, Costa Rica

Whether you’re in the infinity pool, standing on one of the balconies, or inside the light-filled living room, this five-bedroom cliffside Airbnb has prime views over Tamarindo Bay on the west coast and the surrounding rain forest. But the best perspectives come from the two wooden pagoda-style bungalows—each with its own bedroom, en suite bathroom, and outdoor shower—just a few steps from the main villa, all set on one and a half acres, which feel like a complete escape from reality. From $1,100 for up to 10 guests.

Additional reporting by Meredith Carey.

This article appeared in the September/October 2021 issue of Condé Nast Traveler. Subscribe to the magazine here.