Whether you dream of flip-flops and shorts, or packing up your skis and snowboards and heading for the slopes, there are many great destinations in the U.S. to enjoy winter. Here are six to consider—three in warm climates and three in cold. 

Anna Maria Island, Fla.

This barrier island in South Florida is just seven miles long and one and a half miles wide. Ron Schmedley, who lives in Cincinnati, Ohio, and bought a vacation house there in 2007, says, “Anna Maria Island is the perfect place to escape the hustle and bustle of our busy lives and rest our toes in the sand. The island is what ‘Old Florida’ used to be." 

There is an ordinance that no structure can be built higher than the tallest palm trees, so you don’t have the huge high-rise condos dotting the beach, just the crystal clear water. Numerous restaurants offer seafood right off fishermen’s boats. 

When Schmedley and his family visit, they spend most of their time at the beach, where, he says, “it’s not surprising to see manatees, dolphins, stingrays and plenty of other wildlife while we’re looking out at the water.” 

According to Zillow, the median home value for Anna Maria Island is $1 million as of March 2020. The median home value of homes currently listed is $1.6 million. 

Beaufort, S.C. 

Beaufort (pronounced Byew-fort, not to be confused with Beaufort, N.C., pronounced Bow-fort) is a great destination for anyone looking for a temperate climate during the winter. Located in South Carolina Lowcountry, “our winters are very mild and allow for plenty of outdoor recreation – inshore fishing is popular as are trips to the nearby beaches, golf, biking, and tennis,” says Edward Dukes, a lifelong resident and managing partner in Lowcountry Real Estate.

Beaufort, chartered in 1711, sits on the Intracoastal Waterway between Charleston and Savannah, each just a short drive away. Hunting Island, 15 miles from town, offers an “amazing beach, bike paths and a canal for kayaking, paddle-boarding, and fishing,” says Dukes. He recommends buying a vacation house right in the town, which is rich with history and Lowcountry architecture and culture and an easy walk to dinner, shopping and the University of South Carolina’s Performing Arts Center. You can also buy properties in nearby gated golf and beach communities and, if you like boating, you can buy in a neighborhood with a community dock. 

Homes in Beaufort have a median value of $228,654 according to a May 2020 search of Zillow. Home values have risen 5.1% over the last year, making the market “very hot,” according to Zillow. 

Phoenix, Ariz.

Encompassing Scottsdale, Paradise Valley, and Mesa, the Phoenix area makes outdoor living in the middle of winter easy and fun with lots of sunshine, little rain, and mild temperatures. Combine golfing, hiking, tennis, biking and swimming with visits to the Phoenix Art Museum or the Heard Museum dedicated to American Indian art and history or to a performance by the Phoenix Symphony, Ballet Arizona or the Arizona Opera. 

Phoenix was hit hard during the housing crisis, and while prices continue to normalize through 2019, they are still below the peak. According to Troy Reeves, owner of The Reeves Team, "While housing prices have had growth at a slightly faster than average pace over the last few years, it is mainly fueled by the fact that prices previously were too low and we have been catching up to where we need to be all along." 

The median home value in Phoenix is $269,175, with the median home listing priced at $289,000, as of March 2020 via Zillow.

Jackson Hole, Wyo.

Jackson Hole Mountain Resort took first place in Ski Magazine’s list of top ski resorts in 2014 and the magazine continues to heap praise on the town. But downhill skiing is only one choice for getting outside: You can ski cross-country on groomed tracks or into the national parks and forests, snowmobile around nearby Yellowstone National Park, take a sleigh ride through the National Elk Refuge, dogsled, helicopter ski, snowshoe and ice-skate. Since 97% of Jackson Hole’s land is currently permanently protected from development, properties on the remaining 3% are pretty scarce. As a result, dollar volume and transactions are extremely high. 

Kelli Ward, an associate broker at Jackson Hole Sotheby’s International Realty, says that “Wyoming is one of the friendliest states in the U.S. for people relocating for the purposes of…trusts and overall asset protection.” But, “that is just a bonus to some who want to be in Jackson Hole for the beauty of the land.” That is apparent as soon as you fly into the area airport: It is the only airport in the U.S. located in a national park, and passengers get a look at “huge views or the Tetons, which are absolutely breathtaking” even before their plane has landed, Ward says.

In Nov. 2019, the median home value listed in Jackson Hole was over $1.4 million, per Realtor.com. A 7-bedroom, 9 bath home with 15,000 square feet listed in Jackson Hole is going for $17.7 million. 

South Lake Tahoe, Calif.

Lake Tahoe is huge—71 miles around—with ski areas on its north end (in Nevada) and its south end (in California). The South Shore is the livelier of the two, according to Dan Spano, who went there to ski 30 years ago and never left. According to Spano, owner of Paradise Real Estate, the south end is also somewhat more affordable.

“People are attracted to Lake Tahoe because it’s one of the most beautiful places on earth and the winters are mild compared to resorts in the eastern part of the U.S.,” says Spano. At the Heavenly Mountain Resort area, you can ski two states in one day and enjoy what Spano says is the best snow-making equipment in the area. 

The real estate market in Tahoe is “very strong,” according to Spano: “San Francisco Bay area residents doing well financially are buying second or even third homes before prices go out of sight.” 

The median home value in South Lake Tahoe is $454,574 per Zillow in March 2020, while the website lists the market as “warm.” The median value of homes is up 1.6% in the last year. 

Okemo Mountain Resort, Ludlow, Vt.

Okemo routinely tops the list of OnTheSnow.com's “Best Family Resort in America” so if you’re looking for a family vacation destination, this might be it. According to Bonnie MacPherson, director of public relations at the resort, Okemo gets this top rating because the family who owns the operation understands that “families are looking for activities they can enjoy together on and off the slopes.” 

Take Tim and Diane Mueller who bought a home at Okemo Mountain Resort in 1982 for themselves and their two kids. They still spend their winter vacation there but now their grandchildren come along, too. The resort boasts “options for every level, available from the top of each chair” with 46 miles of trails, 667 skiable acres and, thanks to snowmaking equipment that covers 98% of the mountain, a “weatherproof” ski vacation. Okemo is a three-hour drive from Boston and just under five hours from New York City. 

SouthFace Village at Okemo offers luxury townhomes, single-family homes, and chalets as well as building lots. A slopeside townhome with just around 1,250 square feet and two bedrooms and three baths are listed for $655,000 as of Nov. 2019. 

The Bottom Line

Whether you like to escape the snow or have fun in it, there are many great destinations to find the perfect winter home. In addition to price, climate and activities, consider if you rent out your home when you’re not there. If you will consider destinations that have lots to offer all year round.