Reasons Why You Should Not Buy A Vacation Property

Reasons Why You Should Not Buy A Vacation Property

Are you thinking of buying a vacation property to live a better life? I've owned a vacation property since 2007 and let me say I should have just rented instead. This post will discuss all the reasons why you should not buy a vacation property.

I understand why people want to own a vacation property. The secret to never feeling homesick while on vacation is to simply buy a property in each of your favorite vacation destinations. So clever right?

In addition, there's a great chance that once you buy a vacation property, it could also appreciate in value. To enjoy your vacation property and then make money off it is a double benefit!

Buying A Vacation Property Didn't Work Out

Well, that was what I thought until I blew my finances up buying a Lake Tahoe condo a couple years before the financial meltdown in 2008 – 2010. At one point, the property was down about 50%. Until this day, the vacation property's value has not fully recovered.

Ever since I was a kid, I've been a dreamer. Most dreams never came true, but it didn't stop me from fantasizing what could be. After I discovered San Francisco in 1995 when I went with a childhood friend to visit UC Berkeley, I knew I had to go West at some point. Life felt so much better than in Virginia.

Soon after relocating from New York to San Francisco in 2001, I discovered Lake Tahoe and told myself, if I could spend six months in San Francisco, two months back home in Honolulu, two months in Lake Tahoe, and two months traveling internationally, how sweet that would be!

Owning A Vacation Property Is Bad For Your Finances

According to a 2022 National Association of Realtor’s Investment and Vacation Home Buyers Survey, vacation-home sales accounted for 13% of all transactions. Roughly 11% of primary home occupiers also have vacation homes.

It sounds nice to have a vacation home, but I can assure you lots of issues randomly pop up once you own one. For example, I recently went up to my place in Squaw Valley for four days.

When I entered, I found blue and green marker doodles all over my sofa and two sofa chairs! I couldn't believe the tenant wouldn't fess up to the damages, nor could I believe the housekeeping didn't report the damage to the front desk and make the tenant pay.

My condo is being professionally managed. If I'm paying 25% of revenue to the property manager, I shouldn't have to spend time inquiring about this incident. Yet things slip through the cracks with property managers all the time.

Rental income is also highly contingent on the weather for ski season. Before 2019, the winters were pretty dry, causing very little income growth even as the economy boomed back in the Bay Area. Thankfully, the 2022/2023 has been incredible!

There's also a strong Spring, Summer, and Fall rental income. Summer is actually the best time to go to Tahoe and is the second-strongest rental income season. If it wasn't for Summer, I'd be losing at least $30,000 a year for the luxury of owning a property I only use at most five weeks a year.

Questions To Ask Before Buying A Vacation Property

Here are a few questions you should consider before purchasing a vacation home. I really want to save you guys money from not making the same mistake I made.

1) Do you sleep around? 

I'm asking you figuratively whether you enjoy sleeping in different resorts. When you buy a vacation property, you are wed to that property until you sell. You're going to be experiencing the same amenities over and over again for years to come.

Alternatively, you can add up the annual cost of ownership, divide by the estimated days you'll use the property over the years, and figure out where else you can go vacation with that type of money. Once you do, you'll start to get excited by the buffet of vacation options ready to take your money.

Owning a vacation property becomes more valuable once you have children. Before you have children, feel free to spend more money and live it up more!

2) Are you a work slave? 

Most American workers average 2-4 weeks of vacation a year, excluding those who are able to work from home. Only after 10 years at one firm did I finally have the ability and the guts to take six weeks of vacation off a year.

Before making Executive Director, I knew taking too much time off would be career suicide. Once I realized I wouldn't be making Managing Director within my desired time frame, I decided to fully enjoy my company benefits. If you can't escape work for more than four weeks a year, you're much better off renting.

The good thing about the pandemic is that millions of people are now able to work from home. Therefore, you can more legitimately work from your vacation property more often so long as it has wifi.

3) Can you make rental income from your vacation property?

Banks are funny. They are much more stringent on mortgages for vacation and investment properties because they assume you require rental income to afford the mortgage. Meanwhile, you're thinking to yourself, I can afford the place on my own, but if I can get rental income, that reduces my credit risk as a borrower!

Rental income is a great way to offset the ongoing cost of owning a vacation property during the 45+ weeks a year that you will likely not be there. The IRS tax laws even allows you to rent out your vacation home for up to 14 days a year without paying taxes on the rental income generated from those days.

But at the end of the day, you must think like the bank and consider any rental income from your vacation place as a bonus. Only buy the vacation property if you don't need the rental income.

Due to the pandemic, my vacation property Lake Tahoe was shutdown for one month during the peak winter period. As a result, I lost out on over $5,000 in rental income.

4) Do you already have the ideal mortgage amount of $750,000? 

The IRS says you can write off a maximum of $750,000 in mortgage indebtedness between your primary and qualified secondary home.

For example, someone with a $500,000 primary mortgage plus a $250,000 secondary home mortgage should be able to deduct all of the mortgage interest from their income.

5) Do you plan to own your vacation home forever?

According to the NAR survey, the average vacation property owner only plans to own his/her home for seven or eight years. That's not a long enough time to withstand a potentially wrongly timed purchase and the ridiculously high 5% selling commission.

Forever is a very long time. But I say if you don't plan to own your vacation property for at least 20 years, I seriously wouldn't bother.

See: Enjoy Your Forever Home, It Likely Won't Last

6) Are you minting money like Oprah?

Nobody needs a vacation property, just like nobody needs 10 pairs of jeans, 50 pairs of shoes, or $20,000+ automobiles. The vacation property market gets hit the hardest during a downturn as people let go of non-essentials first.

Can you imagine losing your job, and losing a ton of equity at the same time? Not good. You better have multiple income streams, strong cash flow, and a financial backup plan if you plan to buy a vacation property.

7) Is your net worth properly allocated?

If you're thinking vacation property, you're probably doing OK with your finances. Just make sure you don't have greater than a 40% exposure to real estate if you want to sleep better. When the financial crisis hit, the average American saw their net worth get wiped out because property accounted for 80%+ of their overall net worth.

8) Will buying this vacation property make your life better? 

If you don't think a vacation property will improve the quality of your lifestyle, then forget about it. I went the expensive route by buying a condo in a great location with a high HOA so I wouldn't have to do anything to maintain my property.

Buying a house would have probably been a better investment, but a house doesn't have three pools, three outdoor hot tubs, a spa, a golf course, ski-in/ski-out access, and restaurants. I paid up for convenience and amenities because I was focused on lifestyle first.

Here's a detailed comparison between owning a condo or single-family home as a vacation property. Even though my friend's mansion in Sonoma County is worth twenty times my vacation property condo in Lake Tahoe, my children still prefer the condo! Our children tell us the truth.

9) Will your children enjoy the property?

Once you have children, real estate becomes more valuable. A vacation property is great if you have children who love going up. They will build fond memories and utilize the property more once they become adults.

However, if you don't have children, owning a vacation property really is a suboptimal use of money.

Don't Buy A Vacation Property

Buying a vacation property can be a wise long-term investment if you buy at the right time. But in order to capitalize on your investment, you must either make rental income or sell. If that’s the case, are you really buying a vacation property for a better lifestyle, or are you simply buying an investment property to make money? Hopefully you can do both.

For the large majority of people, buying a vacation property is a waste of money. You simply won't use the property enough to justify the costs. The memories over the past eight years of ownership have been wonderful. But I sure wouldn't mind having several hundred thousand more dollars in the bank right now!

Related: The Vacation Property Buying Rule To Follow: Lifestyle First, Income Second

Invest In Real Estate More Surgically To Make Money

If you don't have the downpayment to buy a property, don't want to deal with the hassle of managing real estate, or don't want to tie up your liquidity in physical real estate, take a look at Fundrise, one of the largest real estate crowdsourcing companies today.

Real estate is a key component of a diversified portfolio. Real estate crowdsourcing enables you to strategically invest in commercial real estate around the country. Fundrise is the creator of the eREIT asset class.

Another favorite platform of mine is CrowdStreet. CrowdStreet focuses mainly on 18-hour cities where valuations are lower, cap rates are higher, and growth rates are higher. A long-term demographic shift towards lower-cost cities and states is underway. CrowdStreet is there to take advantage.

Personally, I've invested $810,000 in real estate crowdfunding across 18 projects to diversify my holdings. Further, I get to earn income 100% passively as I spend more time taking care of my children.

Fundrise Due Diligence Funnel
Less than 5% of the real estate deals shown gets through the Fundrise and CrowdStreet funnel

Shop Around For A Mortgage

Check the latest mortgage rates online through Credible. They’ve got one of the largest networks of lenders that compete for your business.

Your goal should be to get as many written offers as possible and then use the offers as leverage to get the lowest interest rate possible.

NMLS ID# 1681276, Address: 320 Blackwell St. Ste 200, Durham, NC, 27701

As a vacation property owner since 2007, I hope you've got a good sense of why you should not buy a vacation property. A vacation property is an unnecessary luxury expense if you're still trying to achieve financial freedom. Once you have achieved FI, then go ahead and buy your vacation property if the numbers make sense. This way, at least you can enjoy it more often!

About The Author

83 thoughts on “Reasons Why You Should Not Buy A Vacation Property”

  1. It is almost not worth talking about buying a ski cabin from a financial perspective because it does not make sense from a financial perspective. It’s sort of like a weighing of the financial pros and cons of buying a Ferrari that is somehow more socially acceptable.

    My recommendation is only consider it (with a spreadsheet) from a financial perspective, if you will use it 100 nights a year: it will probably still flunk the test if you compare it to summer plus winter (ski) leasing. And that 100+ nights has to be both “already” and a sure thing for the future. A new policy at a current job means jack, as do ambitions to get your 2 year old skiing in 2026.

    I will only get in about 65 nights at my cabin at Tahoe, and the passion for owning up there and being part of the community is the real motivation. I enjoy the camaraderie among neighbors vs my boring bedroom community here, surviving the harsh climate, blowing snow, having kids on the ski team, working on the house to the extent I can and hiring other people when I can’t, and not having to go home early because there is a storm and I rented an Airbnb (so I can stay and ski it). All these things make me feel more alive and connected.

    To me, the appropriate language to think about a cabin or vacation home is a real passion, first you have to have the passion and then you have to confirm you can afford it. Don’t ever consider using money as the justification. It’s either lying or stupid or both.

  2. The reason you lost your shirt is because you purchased a condo instead of a single family home. Virtually all condos are already in the loss column by having no resale value – even in a bull market. Unless you’re up in years and plan to live in a condo the rest of your life better consider a house instead so you’ll at least have a fighting chance of affording something better.

    1. Thank you for your wisdom Roy. Interesting perspective.

      I still own two condos, both are paid off. My vacation property condo generates about $18,000 – $24,000 net a year. My San Francisco condo generates about $32,000 net a year.

      To me, these semi-passive income streams have value. It means I don’t have to spend time earning ~$50,000 a year at a job, and time is tremendously valuable to me.

      The vacation condo is also being used by my family and my SF condo can house my children if they decide to live in SF. This provides stress relief and housing stability.

      But now, my focus is on investing in private real estate in the Sunbelt via platforms like Fundrise. I believe in WFH and the demographic shift to lower-cost areas of the country.

  3. I spend a lot of time at Squaw myself and considered purchasing at Squaw Creek or the Village. I still haven’t ruled it out, but the huge HOA is a deterrent. I’ve recently looked into lakeview property (with beach access) to have the best of both worlds in Tahoe. How do you feel about fractional ownerships? To be clear, not timeshare, but instead true fractional, deeded, 1/8, 1/7, or 1/6 of an actual property. I feel like that gives me the flexibility to travel elsewhere yet have 6-8 weeks in Tahoe. I know timeshares are a terrible investment, so I’ve been a bit leery of fractionals investmentwise. Any insight?

  4. It all depends on expense/income formula. In order for a property to pay for its own expenses it has to produce the same amount of money that it requires for paying the mortgage +home insurance+ taxes+ maintenance.

    For example Vacation Rentals in Tampa Bay make from $30,000–45,000 a year.

    Property expenses for the whole year will have to be around $33,000 to stay on a safe side.

    Let’s say you have $52,000 cash for down payment.

    With 20% down payment you can afford a $260,000 property

    Your mortgage will be $1,160+taxes$333+$home insurance $100+$HOA fee $410=$2,000

    Management fee 21% $7,000

    Miscellaneous $2,000

    Total expenses for the whole year $33,000

    Given its a vacation home and you will be operate it remotely, you better be off with a maintenance free community that takes care of common elements and grounds. Consider those communities have masters insurance policies, that saves a lot of money on flood and home insurance. Also some association fees cover extra expenses like cable, internet and water. This gives you a better idea of your expenses since most of them already included in monthly HOA fees.

    I hope that helped. If you are looking to buy vacation home in Tampa Bay watch my videos on YouTube “Olga Shahan”

    Buy airbnb in FL

  5. It all depends on expense/income formula. In order for a property to pay for its own expenses it has to produce the same amount of money that it requires for paying the mortgage +home insurance+ taxes+ maintenance.

    For example Vacation Rentals in Tampa Bay make from $30,000–45,000 a year.

    Property expenses for the whole year will have to be around $33,000 to stay on a safe side.

    Let’s say you have $52,000 cash for down payment.

    With 20% down payment you can afford a $260,000 property

    Your mortgage will be $1,160+taxes$333+$home insurance $100+$HOA fee $410=$2,000

    Management fee 21% $7,000

    Miscellaneous $2,000

    Total expenses for the whole year $33,000

    Given its a vacation home and you will be operate it remotely, you better be off with a maintenance free community that takes care of common elements and grounds. Consider those communities have masters insurance policies, that saves a lot of money on flood and home insurance. Also some association fees cover extra expenses like cable, internet and water. This gives you a better idea of your expenses since most of them already included in monthly HOA fees.

    I hope that helped. If you are looking to buy vacation home in Tampa Bay please don’t hesitate to contact me.

  6. I liked that you said that one thing to consider when you own a vacation cabin is to hire a property manager so that you have help with running the property while you’re gone. I have been thinking about buying a vacation cabin but I have been worried that I would end up not being able to take care of it due to my busy schedule. I will be sure to consider hiring a property manager to receive help in taking care of my cabin.

  7. It’s always good to look at both sides of the argument. Thanks for the detailed breakdown. My wife and I live in SF where it’s next to impossible to buy and we also don’t plan to stay in the city long term. We’ve been toying with buy a very simple cabin for ~$200,000 in the mountains as a weekend getaway. We plan to stay in the city for 2-4 more years to maximize our income. We are looking at a cabin as a way to offset the stress of the city but my first instinct is that it’s a bad idea when we don’t own a primary residence but it’s tempting when we can pay cash for a cabin for the price of a down-payment on a small place in SF. Such a tough call.

    Let’s say it all checks out and we decide to buy it. What is the opinion around here on paying cash vs. 20% down with a mortgage? We pay cash for everything else and like to stay debt-free but with interest rates being good right now, we aren’t sure.

    As you can tell, we are all over the place on this, hence why I ended up here.

    1. Hi! I am in the same boat currently! I’m in the East bay but don’t want to purchase a Bay Area home right now but looking into a Lake Tahoe vacation home. We don’t have a primary home. What are the thoughts around this? Thank you!

  8. I’m split between buying a vacation rental in Tahoe or buying a primary residence in Oakland, Ca. I pulled my money out of the market to save for a home (sitting in settlement account with 2.14% yield) but now the market is looking like it’s about to topple over. I’m sick of waiting for the perfect time so I was planning on buying during the seasonal low in Winter. If I find a good deal in Tahoe then I plan on keeping it forever.

      1. I bought my primary home 20 years ago and paid it off. I now what to buy a vacation home. My husband is 59 and I am 53. He makes about 250 per year. Do you think financially its a good idea?

  9. Ashley Johnson

    I liked that you said that one reason to stay in a vacation home is to relax from the stress of work. I would imagine that this would help you recharge and mentally prepare to continue in your job. I would be sure to consider staying in a vacation home in order to help de-stress from the pressures of life.

  10. I bought a vacation home not a condo and I love it. It is on the beach, no HOA and 100 miles from my house.

  11. Enjoyed the article. Gave me pause of my thoughts.

    But in the end, the wife and I will proably be purchasing a vacation home in the Poconos that I can use year round on the weekends. I will only be about a 75 minute drive from home. We will be able to create lasting memories with our young grandchildren. The developement I will be buying in has lakes, pools, mountains to hike, skiing, mountain biking, flat area biking, fishing, kayaking, rafting on the Lehigh River. We are also planning to retire in the home.

    I will be paying cash for the home. So only will be paying taxes and utilities and maintenance.

  12. Last year I purchased a 2 bed/2bath oceanfront condo for investment purposes – cash purchase. It was on my bucket list and is a way to diversify my portfolio (non-retirement) which was totally invested in the stock market. The property is 3.5 hrs away from my home, cash flows and is large enough for my family. I am happy to be limited to the 14 day usage period as I like to “sleep around”. I see a 5-7 year holding period and think I’ll see a little bit of appreciation within that window. I have a number at which I will sell the property in the meantime, I stay abreast of the market trends in the area, and visit a few long weekends during the off season. Frankly, I sleep better on this investment than I do on my stock market portfolio!!

  13. Dwight Lindsley

    Think twice or more before buying any time-share property. We enjoyed one for awhile until my wife died and my daughter and grandchildren moved in with me. I could no longer afford to have or use the time-share. After a year of agonizing communication with the resort owner(s), and trying to find a buyer, I had to pay over $11,000 to give it back to the resort consortium. That took over a year of haggling with the consortium and then finally paying them over 11 grand (mostly for paying their lawyers.) $11,000 may be easy for some folks, but not for a 75 year old with my daughter and her children to take care of. To top it off, although they have cashed my check, almost a year later they still have not sent me the cancelled contract saying that they have lost it! I won’t name the time-share but it is in Arkansas.

  14. As I read through these comments I was surprised by some of the posts. I own 2 vacation rentals, will buy 2 more in the next year. Its worked out great for my wife & I. We over see all the operation, will not use a management company, we started our own. The 2 that we own should be paid off with in 4 to 5 years.

    1. Theresa Henderson

      good afternoon, my husband and i are thinking about buying a condo for vacation rental purposes. do you stay booked enough to make a profit. or do you only see a profit because you are the management company also ?
      Any advise you can offer would be appreciated

  15. Hi,
    I enjoyed reading your article and all the comments that followed. My situation I live in PA and go to Florida a lot…always Fort Lauderdale. My husband and I are now finally debt free completely and wanted to invest in a condo in Fort Lauderdale so I could come and go as I please and take my son also. We plan on moving there full time in about 3 years and buying a bigger place and keeping what we are purchasing now to use as a guest house for our families. What are your thoughts on this situation? I am struggling with my idea now that I have read your article.

    1. Me and my husband are seriously thinking of purchasing a condo in FL in the Destin area. We are in our 50’s and are thinking of future vacationing just us together. And when our 20-something sons marry and have families we can all vacation together. We are not huge vacationers to go all over the place and we really like it on the beach. Reading all of these comments make me wonder if its a bad idea or does it depend on your age. When I was in my 30’s-40’s we were too busy with the kids to do anything for us. Now our finances are better and we have more time. What are your thoughts?

  16. Love the information and content of the site. The Wife and I have decided to forgo a vacation cabin in order to pay our mortgage off. We both have dreams of a cabin for our family to enjoy for generations, but investing takes priority for long term wealth building. Reading this article reinforced our goals and priorities, which occasionally need to be regulated. Thank you.

  17. Susan Lawson-Bell

    To add my 2 cents and keep this thread going into 2018, here’s my story: In January 2014, near the bottom of the housing market, I purchased a small house on the Gulf Coast of Florida (about 8 miles inland from the beach and above the flood zone). It’s a cute mid-century affair built of brick and block–sturdy as a rock. Paid cash and spent additional money renovating. To recover my investment I’ve been annually renting the house. Although I live over 1000 miles away, I’ve found it easy to manage the property from a distance: I’ve had very good luck with contractors, services, and tenants and I have service contracts for pest control, AC maintenance, lawn care. Problems do come up: plumbing issues, broken major appliances, some goof knocks over the mailbox, things of this ilk. I order things like appliances or mailboxes from Amazon, Lowe’s, or Best Buy delivered; and mail checks to the services and handyman as needed. I pay my contractor to inspect the property annually. I haven’t been there myself since 2015–my tenant emails photos of the property if something needs work or if I request updated pictures. Hurricane season is always a concern, and my biggest annual cost is the insurance policy, but so far so good. The rent check comes like clockwork each month and there’s always a good annual profit. I plan to keep the place indefinitely. But…it’s not a vacation property yet. I’ve only stayed there when I was working on the place or prepping it for the new tenant. At this stage in life I need the income and the house is still paying for itself. But “some day” I hope to have it as a vacation house so I can be on the lovely Gulf Coast enjoying that emerald water and white sand. In the meantime, I’m earning equity as the property value has more than doubled. So I would say the investment was sound, no regrets there, but I don’t have the vacation property that I hoped to purchase.

      1. It’s great to hear you will be using your vacation property as intended when purchased many years back. Nothing like sharing what you love with your young child! Having that vision years back and knowing now that you’ll achieve it–that’s the best in life. Have a wonderful family trip in beautiful Lake Tahoe. I wish the best for you and yours.

        Your article “The Vacation Property Rule to Follow: Lifestyle First, Income Second” is wonderfully apt. It’s clear to me that one of the most important factors in buying a vacation home is that it must be in a location where you will want to spend time for years to come. Anyway, you give me hope that I’ll have the opportunity to use mine one day. It’s certainly an investment for the long-haul!

        Here is an encouraging life-style vacation property true story: A friend of mine is joint-owner with her siblings of a lake-side cabin, where she’s spent part of her summers her whole life. Her grandfather bought the cabin in the first half of the 20th C. In the 1970s her Dad and his siblings inherited, and her Dad later bought them out. Before he passed away, Dad set up a trust to help fund and manage the cabin, and my friend and her siblings inherited a few years ago. At the cabin they have extended family time (including the cousins), as well as their own private weeks each summer. In the trust Dad put some rules in place about how the place is to be used, so no one person can overstay or move in permanently. Visiting their cabin, with the memories it holds, is one of my friend’s and her children’s favorite experiences, as it is for her extended family. It’s turned out to be a great long-term vacation home investment on their Grandfather’s part.

        I plan for my son to inherit my investment/vacation house (if all goes well and I’m able to keep the property for life). He doesn’t like hot weather or the beach. He loves the snow and the mountains. So I hope one day he’ll be able to sell the house and buy his own cabin in the woods.

  18. I didn’t see this mentioned yet so just as food for thought (since I haven’t tried it myself), you aren’t necessarily tied to only vacationing in one place if you buy a second home. You can join a house swapping site and offer your second home in exchange for a free stay somewhere else.

  19. Winston Lee

    I bought a vacation house in Three Rivers by Sequoia National Park. i rented it to long term tenants for 13 years and now I have moved in. Meanwhile the mortgage is paid down and I have 50% equity and I can rent a room out if I feel like it cuz it’s a big house…too big for me and my dog. Then I can go to LA one week a month and do work and earn $3000 in one week. Works for me.

  20. I own four vacation homes. One in Orlando and three in the Outer Banks of North Carolina. I sold one house and made a million dollar profit. I lost monthly cash flow on the others but have gained a lot of equity. One home we have owned for almost 20 years. Its beach front property and when we pay it off it will generate about $50,000 net annually after management and maintenance expenses. The greatest thing about the property is the memories we have with our family and the fact that when I die we can leave it to our kids and their children to enjoy and receive income from. I do agree that in most situations a vacation properties are not a good “investment”, but if you love the beach as much as we do and you buy in a very strong rental area they can be good. You just have to really know the market, pick your spot and be in it for the very long haul. Even though we lost money on one of the properties it will soon be paid for completely and generate $500,000 in income over the next 10 years free and clear plus we get to use it. This was I property I planned to own forever for the kids. Also, my circumstances are different as I only live three hours away and am self employed. I think the key is buy something you really love but that also produces a great income. If you ever tire of using it, you will still have the income.

  21. What is an alternative option from Reality Shares, it requires a net work off over 200k, we aren’t all in that situation?

    1. Fundrise. They have eREITs, which look particularly interesting. It’s free to sign up and explore. I’m biased towards their Heartland eREIT b/c valuations are so much cheaper in middle America. The minimum to invest is only $500 I believe. Check it out!

  22. Hi Sam- I’m curious on what your thoughts are on investing in a vacation home solely as a rental property. Specifically my husband and I are considering buying a well-priced condo in a Northeast ski area with the sole intention of renting. Obviously this is more of a risk than buying a rental-property in a city where we could lease annually, but the low sale price/taxes and HOA fees in the mountains seem to compensate for that.

  23. Question for you Sam…knowing what you know now- would you have been better off purchasing a home in Tahoe? You mentioned you have high HOA fees. We are considering buying a rental property in south Florida and can’t decide if we should purchase a house within a mile or so from the beach or buy a condo right on the beach (with high HOA fees though). We hate the maintenance of a house:(

    1. Yes, a SFH would have retained its value better b/c my resort was getting pummeled by those who decided to welch on their debt. HOA fees are high with condos, and much less with SFHs. But, I wanted to optimize for lifestyle.

  24. We bough/built our vacation rental 3 years ago and it been a good/great investment and lifestyle asset. It is cash flow positive (with 30% down) based on rental income and based on the market improvements we could sell it for a six figure profit. We have a great property manager who deals with almost all the issues and we spend a week or so in the summer, over spring break and Thanksgiving and or Xmas/New Years there.

    I will say we dont use it as much as I thought because it is 6 hours away (to far for a weekend) and the strong rental season is when kids are out of school. So for us to use it when our kids are out of school in the summer costs us rentals (meaning we are paying to use our house). The plan is for the wife and I to be able to use it a lot in the off season once the kids are out of the house…but that is years away for us.

    The other thing I will echo is it is a very different kind of vacation experience in both a good and bad way. It is really nice to walk into your house and have all your stuff set up the way you like but we spend the first day or so looking at all the things renters have done. They are all minor but it is weird when people have been in your house (even with then pay your money to do so) and moved the can opener or put a small scuff on the wall. Also, both good and bad you know what to expect. There is a great sense of familiarity and seeing your kids grow up over time in the same special place is amazing but the down side is you have done all there is to do and it lacks some of the excitement of seeing something for the first time.

    Overall we love our vacation rental and it has been a great decision both from a quality of life and financial stand point. I think we lucked out when we bought (all luck) as prices were very low and at some point we will have a paid off house that brings in a good chunk of income. My advice would be to if you have a lot of work flexibility to find some place that rents well “in season” that you enjoy using “off season”. The ROI is more on the “free” time you get to use it when it is unrented more so than the income/appreciation…IMO.

  25. I’ve thought about buying a “home in the sun” many times over the years, and am now so glad I never took the plunge. Being from the UK we have a large variety to choose from – Spain, Portugal, France, Bulgaria etc etc – in terms of both price and property. I like the US though and thought about Florida and SC for many years, especially post 2008 when the market collapsed. But, as you say in your sign off, when I look in the rear view mirror with the cash in my bank (and remember many great holidays in many different places over that time) I’m glad I never nailed myself into one particular place.

  26. I have what could be considered a vacation home but really it’s a second home with primary residence potential. I don’t think of it as an financial investment but as a life style investment. The life style is a big part of my life. I would never consider renting it out. The house is located 1 hour from my primary home so it is well used and doesn’t prevent me from vacationing in new or far away places. I don’t have to take time off work to use my vacation home.

  27. Hi Sam! Huge fan of the blog but never commented :)

    I feel like owning a vacation home is a “dream” of many. I was in that camp for a while and still find myself daydreaming of my own quaint little cabin in a mountain town in NC from time to time. However, I could never justify the expense. There’s just no way we could get enough use out of it to make it worth. Heck, we just purchased a rather large house and haven’t even fully furnished this place yet, there’s no way I would want to furnish a vacation home that I’m only at a few times a year!

    Great advice, as always :)

    1. Thanks! And congrats on your purchase.

      Maybe you can simply enjoy taking a vacation in your new house for years to come! This is how I’ve tried to structure my house with the bathroom expansion and sanctuary.


  28. I want to go on january or feb to lake tahoe.
    Was looking for a house by the lake instead. Around which area is the best one sam? I was leaning toward south of lake tahoe but ibhave no clue which location is better, north , south, east of the lake?

  29. Great article and great site! I’m an avid reader and just flew into SF today. I would love to meet you if you are free this week! I’m in town working for an investment bank myself. :)

      1. Yes we have a nice expense account! :). Can’t seem to find your email directly on here? I logged mine when I submitted my comment.

  30. BeSmartRich

    I agree with you. Why going to the same spot over and over when you can explore places that you have never been to? Right? All the maintenance fees can be used to pay off real vacations! Haha

    Thanks for sharing!


  31. Not for me. I would rather use points, or rent timeshares than own one. I don’t see my family going to the same place every year (never did it as a child either). I also like to combine work trips into vacations by extending the dates, that gets us vacations at lower costs in new place.

  32. Agreed – vacation properties are most often bad on your finances. You touched on the allure of them though. Vacations are supposed to be fun and carefree and people simply attach that concept to what owning a vacation property would be like. Even if they are mentally aware of the drawbacks, the emotional side of the decision making process can overrule.

    1. There’s an allure, just like there’s an allure for timeshares, which is even worse.

      Definitely check out the place you are considering buying multiple times, and running the cost to own vs rent before buying. I did that, and still bought… which means it’s still an emotional decision.

  33. EL @ Moneywatch101

    Up to this point I have not considered buying a rental property, and probably wont. I rather just rent a vacation home and move from place to place to experience different areas of the world. IT seems like you want to sell soon, and maybe you can realize a good profit.

    1. I will probably never sell, as there’s a lot of sentimental value to my place. My goal is to just pay off the mortgage within 20 years, and use it as an extra cash flow stream and hope rents and values rise aggressively as the Bay Area population growth occurs.

  34. Nuclear Real Estate

    I do not own a vacation home, nor do I have plans to buy one in the next 5 years, however it is part of my 10 year plan.

    I agree that it is not worth the money and not the best “investment”, which is why I have not purchased one already. Every time I ran the ROI numbers it always makes more sense to invest in a local long-term rental and then pay out of pocket for a vacation.

    That said, what changes the equation for me is specific challenges I have with my sleep, where I am very specific about the mattress / pillows / white noise machine etc. that I use. Having my own vacation spot where I could ensure I have a matching mattress / pillow / white noise / etc. would be well worth the price premium to me. I wouldn’t view this as an “investment” I’d view it as spending more on something that would make me enjoy my vacation more. No different than choosing to stay at a more expensive resort, or spending more to get a room with a view.

    1. If you can afford a vacation property to the point where it doesn’t need an investment element to it, then, vacation properties look more digestible. That’s how I looked it it when I bought (I wanted to buy a vacation property in every location I saw myself going so I could feel like I was going home each time).

      But, 8 years later, I wrote this post to warn folks that you will look back and think about all the money you spent, and wonder whether you made the right choice.

      I’ve had some awesome, awesome, memories up in Squaw. They are priceless. I do wonder if I could have gotten similar awesome moments if I had just rented.

      Related: Buy Real Estate For Lifestyle First

  35. Very good post Sam. Long time reader now, and enjoying it very much. I’m in the upper snack bracket of people who read your site and can tell you that, in my opinion, you have excellent and relevant insights on many topics. Well done!

    On this topic, I also think you are right on. I’ve owned two vacation properties in addition to an expensive primary home in a great HCOL city. One vacation home worked and is working brilliantly – very proximate to the city so very heavy use, family loves, totally tuned to our needs, expansive, private, reasonable to maintain while clearly a luxury. But wow, what a luxury for a lower-middle class kid like me to grow up to own and have for my family to enjoy. Almost unreal.

    The other property was on another continent. It failed every test and should never have been purchased. We didn’t use it, rentals did NOT cover costs, it broke down (in a minor way, but still) very frequently, management was not entirely reliable, we were subject to whims, weather and crime (although nothing bad happened).

    In short, choose very carefully and follow the advice above. It is excellent guidance.

    1. Howdy Biggrey,

      Thanks for being a regular reader! I’ve always wondered about buying foreign assets since it fel like the US dollar is on a way way path to massive depreciation. But now, the USD is strong like ox, as I wrote in my private newsletter last week. I’m looking again.

      I love Rio de Janeiro and island property in Malaysia (so cheap). But realistically, I will probably go once a year. It will feel like such a waste!

      Vacation property is truly for those with too much money on their hands. Folks who can buy three plus Porsches, and 10 pairs of the same shoes or clothing in different colors.

      1. The prevalence and facts behind 2nd home (vacation home) ownership clearly paints a true picture – it is largely “aspirationals” as Tom Stanley would have called them (RIP Tom) who are the buyers.

        I could afford the 3 homes I had at the time without missing a beat. But that does not change the logic that I did not need them and the 3rd one failed the logic test completely once the emotional aura wore off over 3 or 4 years.

        I am a very big fan of considering a lifestyle investment in a 2nd home if, and it’s a big if, you can EASILY afford it for the long term and that is what you really want as a part of your lifestyle. By easily afford it, I mean pay cash. A high bar, but a serious one to consider in my opinion.

  36. I’ve definitely thought about it, but I don’t think visiting the same place every year would excite me. At least while I’m still working a day job. I’ve got more vacation than some (20 days + holidays), but I still can’t imagine staying in the exact same place every time. Plus, as you’ve mentioned, it may not pay off as an investment.

    1. Yeah, you gotta do a test vacation at the place you are considering buying multiple times before actually buying.

      Squaw has become an anchor spot for me during the winter and summer for about four weeks, as I spend about 6-7 weeks a year traveling elsewhere.

  37. I have a timeshare that I wish I had never bought. It sounded good when I bought it; never pay for a vacation again! Except for maintenance fees. Which for a single guy, yearly maintenance fees are more then I spend on vacations. And I don’t really need a 4 bedroom resort room either. One is just fine with me.

    Getting rid of it is something I’ve been putting off, cause it could be useful in the future, but probably not, and I don’t know enough to get rid of it.

  38. My family and I are expats and go home to visit the grandparents for about 4 weeks per year. After we outgrew staying in their basement, we thought about buying a house nearby, but leaving a house empty for most of the year didn’t make sense. So we paid a bit more and bought a home 40 minutes away in a resort town with strong short term rental demand. Now do nightly rentals and stay in the home when we return to the states to visit family. It made a lot of sense in our situation, but I agree that it doesn’t make financial sense in most situations.

    1. 40 minutes away is a nice short distance. Makes usage so much easier, as you could literally go up every weekend of the year no problem. My place is 3-3.2 hours away, which makes it somewhat of a trek where I’d like to stay for at least three nights.

      1.5 hours, like Napa would be perfect. But there’s no skiing and no great lake in Napa/Sonoma.

  39. I thought about this briefly, but the management and responsibilities that go with owning property didn’t fit well with my current temperament and lifestyle. Currently a Hilton Resort Club owner which has been a interesting and more practical alternative for my wonderlous and youthful adventures.

  40. I can’t imagine for the life of me why someone would want to own a vacation property. There is no way that it’s worth the money, regardless of how wonderful the vacation is. You going overseas? Stay in a hotel or hostel instead.

    Oh, by the by, I just nominated you for a Sunshine Blogger Award. It’s not an actual award. Check it out:

    ARB–Angry Retail Banker

    1. Lots of benefits:

      1) You own a place that you love and have and want to great wonderful memories there
      2) It’s relatively close to where you work, so you can go there often
      3) You can write off the second home mortgage if under $1M total w/ primary
      4) You could make money in principal value
      5) You’re utilizing your excess cash for experience/lifestyle instead of hoarding it
      6) There’s diversification of assets

      But, only if you have a lot of money should you bother buying a vacation property or three. I would say it is not worth it for 90% of the people out there!

      Thx for the nomination!

  41. Own a small cabin with other relatives (inherited my share) that grandparents originally built, but probably gets used only 4-6 weeks/year by everyone in our extended family (closed for winter, November-March).

  42. theofficialjohnandre

    My parents bought a vacation home in Cape May, NJ in 1998 and did really well on it. Only problem? I get bored after 5 days….the only time I go is to show friends around, I like variety in my vacation.

    1. If my parents could afford to buy vacation properties in nice places, I wouldn’t mind!

      I suspect Bank of Mom and Dad vacation properties are becoming very prevalent given they’ve been able to invest in the greatest bull market of all time.

  43. I’ve lived in multiple states in my journey so far, and Tahoe is the only place I’d consider a vacation home, mainly due to its year-round vacationfulness, and proximity to Silicon Valley. That said, I don’t ever have any plans to buy one.

    I’d much rather sleep around, vacationally-speaking, and try a different place each trip, even when visiting someplace familiar like Tahoe.

    1. It’s kind of like your favorite dish at your favorite restaurant. Once you know what it is, b/c you’ve test vacationed there multiple times, why risk anywhere else?

  44. Not looking at all – although I was tempted especially in Charleston. The beaches are wonderful!!!! I could only see alot of expenses!

    1. Good decision, I purchased my vacation dream home and it is a nightmare and I regret it. The purchase is having a mental, physical and financial cost. I would suggest NEVER buying a vacation home, save yourself the agony. I wish someone had warned me, I am warning everyone that may read this post. Please do not make the same mistake that I did.

  45. We spent an amazing week last month in a pretty nifty mountain house (cannot call it cabin, it’s big) owned by a very close friend. I thought we do need this, it would be great to just leave the city and enjoy the mountains

    Husband was smart enough to list me the cons: the costs, the fact you’ll have to vacation there more than you’d probably like (you’ll feel bad for having a vacation home and not using it, right?) the ‘chance’ to get ‘visited’ by burglars etc.

  46. Every time I go on vacation, I think to myself… it would be great to buy a vacation home and go on vacation to my own home. My stuff would be there, I wouldn’t need to pack and unpack, I could rent it out when I’m not using it and create another stream of income, I’d put down semi-roots, get to know some new folks in that area, blah blah. It feels so sexy.

    Then I go home, realize my faucet is leaking and I need to just buy a new rubber washer or there’s some other thing to take care of in my regular house. And then I realize it’s just really nice to go to a place I’ve rented and leave without headache. :)

    I’m also of the mind that I think my vacations will be to a multitude of destinations and not just one over and over again. That said, your condo is Squaw Creek is nice (and cool you can split it up like that) and if I were to get a place, it’d be a condo.

  47. I can imagine how important a good property manager is when you own a vacation home. With so many people coming and going they really have to be on the ball to keep track of guests and damages. Sorry to hear about your sofa – augh the nerve of some people. They should have tried to wash it out at the very least.

    I’ve been to a few resorts where there sold time shares and boy do they like to lure people in with free food and drinks. It’s fun to go on the property tours and see all the amenities, but be prepared to walk away if you don’t want the commitment – those sales people can be very crafty and being in vacation mode can cloud one’s judgement if you’re not careful.

  48. Ali @ Anything You Want

    I don’t own a vacation property and have no plans to purchase one in the future. As you put it, I do like to “sleep around,” preferring to visit a different location each time I travel. I wouldn’t want to be restricted to staying at my vacation house. I also wouldn’t want to be tied down by the time, effort and money required to maintain a second house. I love to vacation, I’d just prefer to do it in someone else’s house!

  49. SavvyFinancialLatina

    I like exploring new places. I don’t want to be tied to one area unless I’m planning to live there for a long time.

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