How to Find Your Second Home


Where to Start, What to Know

My husband and I recently purchased our first vacation rental property in Northwest Florida. This did not happen overnight, it was years in the making. Much thought and consideration went into research of the housing market, types of properties, costs, return on investment and how we would manage the property from our primary home. Now, we have family who are considering purchasing their own winter home property and wanted to know where to start and what to consider.

Of utmost critical importance is to determine whether you plan to buy a true investment property, which is one that is largely rented to guests versus a second home, which is vacant for most of the time the owner isn't there. Everything else will relate to your primary objective: financing, location, price, type of home, management, insurance and much more all tie in to the property's primary purpose.

Never lose sight of the fact that location will be paramount to the very next steps to purchase your second home, particularly the cost of your investment home. As the climate gets warmer or closer to the golf course, mountains, water way or beach, the price will go up. Same with property type, size, age and amenities. Price relates to all of it. If you get the best location based on your objectives, it will be less likely you have buyer's remorse. Therefore you need to establish what you can afford to spend on your property, as well as what a bank will lend if you are financing it.

I've included a personal account of my search for a second home as well as insight from other's experiences with their own search. Please feel free to contact me with your own goals and objectives and first-hand accounts.


Real Estate TV Shows are Invaluable Educational Tools

When I mentioned years of research prior to purchasing our own vacation rental investment real estate, I mean YEARS. Looking back, I was always hoping that I was prepping for my/our future purchase, but hopes and reality don't always line up. It may seem like a pipedream, but conscious steps to educate yourself are ultimately going to help you reach your goals because no one but you can actually turn that goal into a reality through your own choices and actions. Who knows? You may decide it isn't a good idea to own your place now or ever and that's OK too.

I watched many, many seasons of real estate shows on networks such as HGTV and I must say, at the time I felt that maybe I should be doing something more productive than another marathon of "Beachfront Bargain Hunt", "Vacation House for Free," and "Flip or Flop." More recently, HGTV's "Vacation House Rules" has been another go-to show that I watch, as does my trusted advisor, my sister.

Real estate television shows are entertaining, informative and invaluable for minimizing your own mistakes, objectively seeing real estate from a different perspective as well as empathizing with others that there is a lot to learn and things will go wrong. If you learn and grow, then that is the best outcome.

Price, Location, Type of Home

As I stated above, price, the type of home and location are all interconnected. We considered every possible price point from less than $10,000 on up. Location will determine price, as well as other factors such as type of housing and amenities. Don't overlook the impact of homeowner's association fees, property taxes, property restrictions and more.

This is a brief overview of our search for a vacation rental investment property:

I found a fairly new, beautifully furnished park model home in South Walton County of Northwest Florida that included half an acre of land in a pine forest for $110,000, which is expensive at $1,100 per sq foot. For comparison, I also searched the Orlando, Florida area and found an aging, furnished mobile home with an attached screened sun room and parking pad that was listed for $8,500. Lot rent would be an ongoing expense for the Orlando option and all of the furniture would need replaced. We were not serious about purchasing a park model, but for the sake of completeness, it's important to know what the very least expensive options are in your area of interest compared to the ceiling of your quest.

The next price point we considered was a studio layout condotel property with balcony in the upscale Sandestin golf community of South Walton County Florida. There were several options with a bay view or garden view for approximately $150,000, plus ongoing HOA fees. Although we preferred a gulf-front property, for the price, we were willing to consider sacrificing the gulf view. However, the small size of a studio condotel was a concern and when we learned pets are prohibited, we moved on. Many lenders don't offer bank loans on condotels, which is another consideration.

We also looked at several condo options with either gulf front or Destin Harbor views. These fully furnished properties with a rental history were aging and would need remodeled. They ranged in price from $285,000 to $375,000. However, the deal breaker was large dogs, whether with owner or guest, are banned by the Restrictive Covenants of the very popular beach front resort located on Holiday Isle in Destin, Florida. No matter how tantalizing, there is no point in buying a property where our beloved Golden Retriever is banned.

Of course, the most expensive properties of $400,000+ we considered were what matched our top criteria. Ultimately we chose a gulf front condo with a vacation rental history in the location we were most comfortable with, large-pet friendly for both owners and guests and beautiful amenities. Because of the expensive price, we chose a one-bedroom condo with hall bunks and two full bath rooms. The stunning view of the Gulf of Mexico and South pool were exactly what we dreamed of.

Once we found what turned out to be the best property for us, we arranged for our local real estate agent to show us the condo via a video tour. We had also seen 24 photos of the unit via the online listing. We made an offer based on the video tour and the photos, however, not everyone may be comfortable with that. Only you can determine what works for you, but if you want to see a property in person before making an offer, keep in mind that in a hot market someone else may swoop in before you can arrive for a showing.

Where to Start, What to Know

--Personally visit the area/s you are considering if you have not already done so in recent years

--Consider all seasons of the target area, particularly high/peak season when the tourists will affect traffic, transportation, dining out and much more

--Be realistic about how you and your household will arrive at your new home. If you live in the Pacific Northwest and want a second home in South Florida, then flying is about the only logical option. Once at your destination, can you leave a vehicle behind once you return home? If you your pet and/or your partner have physical limitations, how many days on the road can you tolerate to arrive at your second home? One? Two? Three+? No one is aging backwards, so what works today may not be so great in the next five or ten years.

--Once you determine your target area, sign up with a third party real estate site to get daily or weekly notifications of all properties within the parameters of interest. For example, my husband and I each signed up for daily email alerts in the Miramar Beach Florida area an entire year before we actually purchased our investment real estate. We chose, but there are many others such as Trulia and Zillow and so forth.

--Ask for referrals for an experienced real estate agent if you don't already have one. Your agent can also set up your parameters to receive property alerts.

--If the real estate market is hot, like it has been for 2021, are you prepared to buy a property sight unseen except for photos and/or a video tour?

--Ask a trusted family member or friend to give feedback on the properties you are considering. I was so glad my sister, who lives in Oahu and has no personal experience with Destin Florida, offered a non-biased and totally honest evaluation of each property that we considered. She helped me recognize the deal breakers for several units, including feedback on properties that she felt seemed overpriced for the value. Another example, my sister pointed out that one unit with a 4' stucco balcony wall blocked the view of the gulf for anyone sitting on a chair or sofa in the main room of the unit. Why pay for a gulf front unit if you can't see the gulf when seated?

In summary, the single best strategy we employed was signing up for online property alerts. This immensely helped us personally know the target real estate market and ultimately, it was the secret weapon that helped us find "the one" that we purchased. Your real estate agent can help of course, but unless you do your own homework, you may always wonder if there was a bigger, better deal that you missed. I have not one regret over the choice we made, because I know we did everything possible to research the market and make an informed buying decision.

To view the property we purchased, please visit for a photo tour, rates and availability. We hope to someday host you as our guest.


"Sometimes the smallest step in the right direction ends up being the biggest step of your life. Tiptoe if you must, but take a step.

-- Naeem Callaway, American, Founder/CEO Get Out the Box, Inc., a 501(c)(3) Non Profit Organization dedicated to educating and mentoring at-risk youth in low income and rural communities

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