Landlording & Rental Properties

Sound Advice for Buying a Vacation Home You Won’t Regret

Expertise: Landlording & Rental Properties
61 Articles Written

The best place to buy a vacation home depends upon you and your family's interest. For example, if you like doing beach activities, then you need to purchase something near a beach, or if you like skiing, then Jackson Hole or Aspen, Colorado might be a good choice for you.

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Here are few points to consider BEFORE you buy a vacation or second home.

What is the Purpose of Buying a Vacation Home?

Are you buying a vacation home for pure investment purposes, for family fun, as a future retirement home, or perhaps your reasons are a combination of some of these factors. Before you buy, you need to have a well-defined and written out purpose for why you are looking to buy a second home.

You need to make sure you write the purpose down and reflect back on it during the buying process. This will make sure you are staying on track with your goal, and it will keep you from making an impulse purchase that you will regret down the road.

Set a Budget and Stick to it

It is important to always remember that buying a vacation home is a luxury purchase — it is not a necessity. There is nothing more heart breaking than to have a vacation homeowner come into your office and explain to you the financial hardship owning a vacation home is putting on their family.

Related: How to Jointly Buy a Vacation Home Without Destroying a Friendship

To avoid this, I recommend paying cash for a vacation home and not financing it. If you don’t have the money to pay cash right now, that is okay. Simply wait until you do have the money before you make the purchase. Remember, life is a marathon, not a sprint. Most often, taking your time and being patient pays off.

Be Realistic in Your Expectations

If you are purchasing the property for pure family entertainment, be realistic on how often you are going to be able to actually use the property. If your kids are younger, then it is a little easier, but as they get older with school functions, sports, extra circular activities, and them just wanting to hang out with their friends will probably cut into how much time you will actually spend at the property.

If you are looking at it for a pure investment opportunity, be cautious when evaluating the money the house can bring in. Oftentimes, buyers get so excited about buying a second home that they make the numbers look better than they ever could ever actually be.

Return on Investment

You should see your biggest return on your investment when you go and sell the property. To make sure your house has a great appreciation rate, here are a few points of consideration:

What’s the Main Draw to the Area, and is it Stable? 

What makes people want visit the area or buy a house in the area? You should do a little research on the area and know the future plans. Obviously, you do not want to buy a vacation home in the wilderness, only to find out that a major highway is planned to go right through your property.

Builders and New Properties 

Are there a lot of builders in the area? Are there plans to build a lot of new houses? Remember, new houses keep prices down on existing homes, so this will hurt your resale value in the future if a lot of new houses are being planned to be built.

Have an Exit Strategy

Even if you are planning on owning the property for a long time, you should still have an exit strategy. This strategy is oftentimes hard to come up with, especially before you actually buy the property. However, you should think through how you would plan on getting out of the property if you have a financial downturn or if you really have to get out of the property quickly.

Related: The Pros and Cons of Fractional Ownership of a Vacation Home

Considerations for Those Purchasing for Investment Purposes


Is there a large demand for long term or short term rentals in the area? How many weeks a year can you expect to have occupancy in your vacation home if it is set up on a short term rental? How easy is it to attract renters?

Supply & Demand

Is there a proper amount of houses for the demand? You don’t want to get into a situation where there is an oversupply of vacation homes as compared to the demand.

Check the Affordability of the Houses

Here in Orlando from 2006 to 2008, if I heard it once, I heard it a thousand times: “Houses always go up in Florida.” Well, that is not always the case. Make sure the vacation homes are affordable and have not appreciated beyond what is normal.

Investors: What considerations have you taken before buying vacation homes? Have you ever bought a second home you ended up regretting?

Leave your best tips and stories below!

Trey Duling is the President/CEO of, a large travel company specializing in Florida getaways. He has over 27 years of...
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    Edward Briley None from Virginia Beach, Virginia
    Replied almost 6 years ago
    Buying a vacation home will most likely be something in a few years you may regret. When I was a teenager, my parents decided to buy a vacation home in the mountains. What a disaster that turned out to be (for me). Now don’t get me wrong, I loved going to it, and I enjoyed especially the evenings and night. One thing I should say, is that I am the youngest son. Well needless to say, my sisters and brother would go up there and stay a few days here and there, however, maintenance was not their intent. No one mowed the grass, no one fixed the problems. That was left to me and my parents to do. My parents eventually moved up there, and age took its toll on them. Needless to say they had to move back to the city close to medical facilities etc… However, the place was still there. Medical bills got higher, and the usual story. Well needless to say, brother and sisters could not take care of it or cared to. It was sad, but it became the nuisance of the family. My dad passed, and it was out of the question for my mom to sell it. Time passed and my mom passed as well. My youngest sister asked to buy it from the family, because she had good memories from there. The family agreed, we sold it to her. Of course the place is in desperate need of repair, but at least it is still standing, however, not habitable. When her family goes there, they put up a tent, or rent a trailer. However, they use the bathroom in the house. Now to say this taught me a lesson of wanting a vacation home. They are very expensive, and very time consuming to keep up. To take your family on a vacation, will mean nothing other than work while trying to enjoy the area. Not to mention it is going to double your vacation cost. It will be difficult and it will turn into a nuisance, and that I can promise, especially if you have a large family, because even renting it will cause problems you are not going to want to deal with. And remember the expenses, they keep coming, rather you are using the home or not. Unfortunately, You will realize that owning “On Golden Pond” has more problems than you can shake a stick at. No to mention unexpected wildlife guest to mosquitoes, wasp, etc… I am not going to tell you that I don’t have many good memories from the family vacation home, because of course I do. And I am one that knows that you cannot do anything to change the bad memories, all you can do is make good ones. Now, I am not saying I do not own a vacation home, because I do. Well part of one, and many think that a “Time Share” may be expensive, and a waste of money, and I am not going to say they are the best investment in the world, but the $900 a year I pay in maintenance cost, ensures that I have a rest for 7 straight days, and not have to worry about the maintenance or anything else when I am not there. Plus if my children want to use it, they can, with or without us being there, and it has some other advantages is well. Do I regret buying a time share? I only regret for what I paid for it when it was new, however, now it is the best vacation anyone could hope for. They are not for everyone. My next step will be buying a condo in a resort area, that I will be able to rent out. This will bring the best of both worlds together. ( I hope).
    Sean T. Rental Property Investor from MA
    Replied almost 6 years ago
    Thanks for the article!
    Frankie Woods Investor from Arlington, Virginia
    Replied almost 6 years ago
    Awesome article! My dream is to purchase a vacation home in the mountains of Colorado. I like your idea to pay for it with cash. However, I feel like if I wait, I’ll miss out on the opportunity to get in at a “reasonable” price. Prices are already crazy! Thanks for the tips/advice!
    lissa hall
    Replied almost 6 years ago
    Yeah, Really Nice article Trey. Luxurious house is dream of every one especially for vacation.
    Jeremy Thompson
    Replied almost 3 years ago
    I like how you mentioned that it’s important to keep the numbers real if you are looking into purchasing a vacation home for investment since it’s not entirely uncommon for first-time buyers to be blinded by excitement making the numbers look better than it really is. That is a sound advice since being able to have realistic numbers will never get you wrong. This is also why I’m making sure to have a Realtor to guide me while I’m looking for a vacation home. I would prefer to obtain a beach vacation home since my son loves going to the beach. Additionally, being able to have beach house sounds to be a fine investment. Thanks!