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March 16, 2026

Choosing a Vacation Home for ROL in Retirement

For many seniors, retirement isn’t just a period of their lives or a financial goal. It’s a place. And sometimes, retirement is more than one place.

A beachfront condo during the summer. A cozy cabin in the fall. An apartment near your favorite ski hill in the winter. A cottage near the river for fishing and hiking in the spring. And the homestead lit up for holidays and family parties.

Once you retire, a second home becomes more than just a getaway. It becomes a significant part of your lifestyle, your community, your schedule, your legacy, and, yes, your Life-Centered Financial Plan.

Here are three questions to consider and discuss with your financial advisor to decide if a second home should be one of your retirement goals.

1. What am I “vacationing” from?

When you’re working and raising a family, vacations are an escape from the hustle and bustle of your normal routine. They might even be the light at the end of the tunnel that gets you through another endless morning commute, another tough quarterly sprint, and another round of customer service headaches.

But in retirement, travel can be a regular part of your retirement routine, even if you don’t want the “endless” vacation model of retirement.

If, as a retiree, your travel plans come more from a need to “get away” than from a sense of discovery and adventure, then maybe you’re still too tied to your old routine. Maybe, rather than looking for a second house, you need to rethink where your main residence should be.

On the other hand, if owning a vacation home will let you spend more of your time with a wider group of loved ones and cycle through more of your favorite activities, then maybe you’ve already moved past a “vacation” mentality and expanded your vision of what life in retirement can be like.

2. Will the dream live up to the reality?

It’s easy to get so caught up in your “dream” retirement scenario that you overlook some of the details.

Spending a few “rustic” months every year at that cabin in the woods might sound relaxing. But you’ll still have to pay for electricity. And heat. And water. And homeowners’ insurance. And taxes.

Chopping lumber for your woodburning stove might be fun when you’re 60. What about when you’re 70? 80?

Are you going to rent the property when you’re not using it? Do you want to be “on call” if an appliance breaks when you’re hours away at your main house, or taking a trip to Europe?

Everything you dislike about owning one home gets doubled when you buy a vacation home. Renting might solve some of these problems. But you do need to be prepared for the hassles as well as the fun.

3. Am I close to what really matters?

Weekend golfers might dream of having a second home closer to their favorite vacation course.

Skiers might dream of an extra month or two on the slopes.

But once you do retire, you might feel your priorities shift.

  • Playing more golf might be less fulfilling than volunteering or teaching.
  • Your body might start asking for less skiing and more time around the fireplace.
  • You might discover new interests that lead you to new places.
  • Aging loved ones might make you rethink who you want to spend your time with.
  • Grandchildren might make you rethink what kind of a legacy you want to leave behind.

One of the cornerstones of Life-Centered Financial Planning is flexibility. Let’s talk about what “home” means to you now and what it could mean in the future.

Investment advisory services are offered through Kingsview Wealth Management, LLC (“KWM”), an SEC Registered Investment Adviser. Insurance products and services are offered and sold through Kingsview Insurance Services, LLC (“KIS”), by individually licensed and appointed insurance agents. KWM and KIS are subsidiaries of Kingsview Partners.

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