The top 3 winter holiday destinations to book now

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Interior of Anna Maria, FL vacation rental

Talking about the winter months before the Fourth of July may feel a bit like sipping a pumpkin spice latte at a Memorial Day barbecue. Still, it's never too early to start planning your travels if you want the best selection of vacation homes to choose from over the busy holiday season.

Vacation rentals are ideal accommodations to call home for the holidays, providing ample living space for your family to gather, fully-equipped kitchens to cook a bountiful meal, and extra room to deck the halls. And if you book a pet-friendly home, even furry family members can join the celebration, too.

Over the last two years, travel has looked a little different and many gatherings took a hiatus, but still, 58%* of people planned to travel last holiday season according to our Holiday Forecast and Winter Trends 2021 report. If that is any indication of what demand could look like this year, we suggest booking sooner rather than later—especially if you are hoping to visit one of these three most popular holiday destinations, based on current Vacasa bookings.

1. Anna Maria, Florida

A “White Christmas” doesn’t have to mean snow. Consider trading in white-capped mountains for the white sand beaches of Central Florida. Anna Maria is a charming destination along the tropical Gulf Coast, averaging mid-70s in December. Take a stroll down Pine Avenue for local shopping or to enjoy fresh seafood and live music at one of the street’s many restaurants.

In keeping with the holiday season, Anna Maria has an events calendar packed full of festivities. Take your pick between the annual Christmas tree lighting, local art market at Winterfest, or the winter water-land of the Holiday Boat Parade—no matter what your holiday crew favors, there will be plenty to do in Anna Maria.

2. Lahaina, Hawaii

A historic whaling-village-turned-Maui-hotspot, Lahaina welcomes many visitors to its shores, but still has plenty of small-town charm. Enjoy snorkeling off the coast, sunset cruises, and whale watching, or stay on land to take in the many art galleries along Front Street. When fun in the sun has taken its toll, you can relax in the shade of one of the largest banyan trees in the United States, located in the heart of Lahaina.

To kick off the holiday season, each year there is an annual lighting of the banyan tree you won't want to miss. The island goes all out with festive decor and hosts plenty of holiday events for all of the family, featuring appearances from St. Nick (who may arrive by outrigger canoe) and carolers around town singing Bing Crosby’s famous "Mele Kalikimaka." Or, celebrate with the Jewish Congregation of Maui and Chanukah candle lightings throughout the month.

3. Government Camp, Oregon

Government Camp sits at the base of Mount Hood, Oregon's tallest mountain, and is an ideal location for outdoor winter adventures. The town may be quaint, but there’s no shortage of local restaurants and taverns, ski shops to browse, or coffee shops to get your caffeine kick before hitting the slopes.

This holiday season, dash through the snow in a horse-drawn sleigh ride or tube down the hills to rock ’n’ roll music and colorful lights. Ready to get out of the cold? No problem—warm up your pipes with a holiday sing-along at the crowd-favorite Skyway Bar and Grill.


Allison+Partners Research + Insights surveyed 1,000 US consumers age 18 or older. The survey was fielded using the Qualtrics Insight Platform, and the panel was sourced from Lucid. Fielding was executed in October 2021.

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