Outdoor pool and patio at dusk, with lounge chairs and distant city and mountain views.

Questions to Ask Before Buying a Vacation Home

May 17, 2023

If you’re thinking about buying a second vacation home for vacation or rental purposes, then you’ll need to do some homework before you get serious about shopping.

Homeownership is a big deal, and buying two homes can either be a path toward long-term income or a mistake that will sink you financially.

Here are the questions you should ask (and answer) before you make any offers.

Why Do You Want a Vacation Home?

I want a rental property for short-term tenants (Airbnb)
I’ve always dreamed of owning a home in ________.
I visit all the time and want a place to stay.
I want to retire here; buying a home seems like a good first step.

What Can You Afford?

Second homes usually require at least 20% down
Mortgage rates are usually higher
Taxes and insurance
Utilities
Maintenance and upkeep
- Cleaners
- Landscaping
- Property managers

Where Will You Buy?

I’ve always known my ideal spot
I’m really not sure
- Spend a week or two in different areas
- Make a list of pros and cons; compare
- Ask locals what it’s like
- Ask other vacation homeowners what it’s like

Is This the Right Home for You?

Is the home conveniently located?
- How far to big attractions and public transportation?
- What are crime rates like?
Does it have a yard? A deck? A garage?
How does it stack up against other homes in the area?
Will you have to make changes or upgrades?
- Can you afford to do that?
Will it be rentable?

Are There Natural Hazards or Events You Need to Understand?

Earthquakes
Mudslides
Hurricanes
Tornadoes
Hail
Snow
Floods

How Much Time Will You Spend There?

Consider tax laws
Factor in to-and-fro travel expenses

What’s Your Exit Strategy?

I want to retire in the home
I need to figure that out
- After its value has increased by $_______
- After I’ve owned it ___ years
- After I’ve paid off ____% of the mortgage

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