Places to Stay

5 Outsized Villa Rentals Worth Planning a Trip Around

From a chic Hamptons farmhouse to a Montana mountain chalet. 
Exterior view of pool palm trees at and Villa Moloch Riviera Maya
Manolo Solís

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After more than a year stuck in our pared-down pods, we're all clamoring to burst out of our bubbles and celebrate somewhere new—and these five fresh rentals are great options for getting the party started.

All listings featured on Condé Nast Traveler are independently selected by our editors. If you book something through our links, we may earn an affiliate commission.

A birthday blowout on the Riviera Maya

A sleek concrete compound edging the Caribbean, Villa Moloch has all the necessary creature comforts (and then some) to fête another loop around the sun: oversized daybeds by the pool, a private chef to whip up celebratory feasts, and indoor-outdoor spaces that flow seamlessly—so you can crack open a best seller in the shade without sacrificing the sound of crashing waves. Sleeps up to 14; from $1,800 per night. 

The Mainstay, Hamptons

Crab Meadow 

A group hang at a revamped Hamptons home

Since its top-to-toe renovation wrapped earlier this year, the nine-bedroom Mainstay will undoubtedly become just that for friends summering in tony Southampton. Set on two acres, the home is elegant and removed but totally relaxed—think, a chic farmhouse with brass fixtures, warm wooden floors, and marble finishings—plus deep-seated sofas for hours of reading and a long, glassy pool with plenty of lounge chairs. A concierge can arrange for a private chef, though you can also fire up the deluxe grill in the backyard and toss a few burgers—or lobster tails—onto the fire. Sleeps up to 23; from $1,300 per night. 

Multigen fun in Jamaica's Discovery Bay

The last year was tough on families, with parents and kids crunched together at home while cautious grandparents missed milestones. Happy Hour, a new refuge on the island's northern coast, lets you make up for all that lost time, on the tennis court or private beach, soaking up the sun or building sandcastles. And at the open-air bar, you can mix up those cocktails (or mocktails) you mastered during quarantine. Sleeps up to 14; from $3,715 per night. 

An adults-only weekend in Big Sky, Montana

Some parents just need a break from the kids entirely. Travel specialist Embark Beyond can arrange a grown-up regroup at Wildridge Chalet in the Spanish Peaks, meaning you and your friends can hit the slopes of Big Sky Resort or miles of hiking trails and be back in front of a fire with a local IPA in hand only 20 minutes later. Plus, stargazing from the back deck is the perfect bedtime story. Sleeps up to 16; from $770 per night.

One of the outdoor spaces at Solvei, in Belize

Will Moreno

An intimate beach wedding in Belize

Set on nearly a mile of pristine Caribbean beach within the confines of Naïa Resort and Spa, the five-bedroom Solvei (Danish for “path of the sun”) can accommodate celebration and relaxation equally. Open for rentals since October 2020, the airy, water-facing home has plenty of private outdoor space where you can recite your vows, plus ample indoor areas to entertain, including a game room with billiards and table tennis—so the fun can continue long after the cake's been cut. Sleeps up to 15; from $4,000 per night. 

A version of this article appeared in the July/August 2021 issue of Condé Nast Traveler. Subscribe to the magazine here.