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Favorite Destinations for Owning a Vacation Home


Stephanie Prince Alexander

Favorite Destinations for Owning a Vacation Home

The idea of investing in a vacation property can be very enticing. But where to start? Unless you have a specific area in mind, finding the best location is most likely one of the first steps for most. To start your inspiration, here are some of our favorite locales, stateside and beyond.

Vail, Colorado

If you’re interested in a winter vacation home, look no further than Vail, Colorado. Vail is one of the world’s most premier skiing destinations and is the largest—and arguably the most popular—ski mountain in the United States. Offering nearly 200 trails on thousands of skiable acres, posh residences, and an array of world-class amenities just steps from the lifts, Vail Mountain is a magnet for discerning jetsetters and dedicated skiers.

In February of 2021, Forbes mentioned that Vail is one of the top ten places to own a winter vacation home and it’s easy to see why. At its base, Vail Village is reminiscent of an elegant alpine resort, teeming with upscale boutiques, Michelin-starred chefs, and laid-back bars serving up cold drinks and warm company. Off the slopes, Vail Village offers every comfort and pleasure, from spas and shopping to après and fine dining.

Los Cabos, Mexico

The popular vacation destination of Los Cabos is made up of the twin towns of Cabo San Lucas and San Jose Del Cabo. San Lucas offers restaurants and nightlife, while San Jose is steeped in traditional Mexican charm. First made popular by celebrities in the 1940s, Cabo is the perfect place to own a vacation home to get away to. International Living agrees, naming Cabo the number two international destination to invest in a vacation home.

Here, where the desert meets the sea, the bright-blue Sea of Cortez—teeming with colorful fish and marine life—meets the mighty Pacific Ocean. Explore the billfishing capital of the world on a guided fishing charters that also scours Cabo's waters in search of marlin, tuna, wahoo, and sailfish. Dive with massive whale sharks or embark on a whale-watching adventure during the gray whale migration. Golfers can choose from six championship courses, including Cabo del Sol’s Ocean Course designed by Jack Nicklaus. When the sun goes down, the buzzy nightlife and high-end restaurants come to life.

Nantucket, Massachusetts

An all-American island that’s attracted tourists for centuries, Nantucket—located 30 miles off the coast of Cape Cod—offers many ways to spend your days. It’s hard to name a more idyllic and timeless destination to invest in a luxury vacation home. It’s easy to get to, offers abundant space, and feels remote. reported in April of 2021 that Nantucket summer home rentals were fully booked—a clear sign of the demand for the area.

With one of the highest concentrations of pre-Civil War structures, being in Nantucket is like roaming a living museum. Though it certainly now has all the creature comforts of the 21st century, wrapped in an elegant, colonial package.

There’s always plenty to do. Indulge in an exquisite seafood dinner. Explore the peaceful beaches that line the island's tranquil inlets and bays on foot, bike, or Jeep. Try your hand at surf fishing. Spend a long afternoon tracking the flight of coastal birds or disappearing between the pages of a book.

Rosemary Beach, Florida

With its long stretches of powdery sands and inviting aquamarine waters, Rosemary Beach provides the beauty of the Caribbean from within the continental U.S. Nearby WaterColor is a master-planned community that gives a small town feel and has incredible charm with green parks and thoughtful architecture.

This family-friendly destination is popular nearly year-round and is a wonderful place to own your own little slice of vacation paradise. In this laid-back stretch of coastline, you’ll find beachside bars, gourmet bistros, and expertly designed neighborhoods along stretches of road leading to uncrowded beaches. Go for a casual bike ride with sweeping ocean views along the communities’ designated paths or opt for a beautiful drive down the 30A corridor’s namesake highway.

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