How to Use Airbnb to Travel & Live for Free in Retirement

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Late this summer, I was fortunate enough to attend the SF Bay Summit, hosted by fellow BiggerPockets member J. Martin in Oakland, CA. Although I was there to talk about note investing and meet new people, I also came home with some other interesting takeaways. It was actually hard not to, as there were so many great presenters, such as Nav Athwal, Kimberly Smith, Chris Clothier, and too many others to list.

It’s great to be able to travel and speak on different wealth building strategies, especially since I can see what others are doing elsewhere, helping me to gain a pulse on what’s happening with real estate investing in different parts of the country. When I hear so many new interesting strategies at once or in such a close proximity, some ideas stick and others fall by the wayside possibly popping up at later times in my career or even daily life.

Things that stuck from this meeting included seeing Nav Athwal of RealtyShares endorsing the use of new technologies in your business, something I took note of, as we are always looking for new efficiencies in our day-to-day operations. Kimberly Smith of Corporate Housing by Owner, LLC talked about furnished corporate rental properties and the benefits of connecting them with executive renters. As our business improves, we’ve started to look at similar corporate space for certain aspects of our company.

Chris Clothier of Memphis Invest talked about out-of-state turnkey property investing, which is a strategy many passive investors we work with enjoy. Just like with re-performing notes, it’s the idea of simply “turning a key” to invest and having property in multiple markets that appeals to them. Even bumping into a fellow BP member, Al Williamson of LeadingLandlord — who I was on a panel with for the last summit and who is an expert in landlording Airbnb rentals — got me thinking of a new strategy. All this talk of using new technology to employ passive or semi-passive investing started to make sense to me synergistically.

They say to make a sale, a prospect needs as many as seven touches before they take action. I don’t know what number I’m at, but after seeing these speakers at last month’s event, along with some other timely situations caused me to re-evaluate how I both live and travel as an investor.


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Although Airbnb is anything but new, it was interesting to hear how people were utilizing this tool not only as renters or as travelers, but also for their real estate investing.

Related: With the First Airbnb Landlord Conviction, Should Vacation Owners Be Worried?

My youngest son (a Millennial) actually got me into Airbnb pretty recently since he uses it to stay wherever he’s traveling. He’s always trying to show me how nice the places are and how much money he saved himself by staying in these places versus a typical hotel.

But, of course, I can’t only listen to my son! He’s a Millennial! What does he know? It wasn’t until that final straw of a consultant of mine coming to town that I finally realized the potential benefits as an investor.

Business Meeting via Airbnb

On a fairly regular basis, one of my consultants flies into Philadelphia from Atlanta and stays in a nearby hotel close to my office. The problem is it’s hard to get a decent hotel without paying at least $200 to $300 a night or more. This year, due to the growth of our staff, our conference room is always busy too, so we would have to lease nearby meeting space to the tune of $40/hour for two or more days. As you can see, the hotel and meeting space alone are easily costing us North of $1,000, and since my firm covers these expenses, we were really hoping to find a better way.

So, my son says, “Dad, let’s try to find an Airbnb. If we find one big enough, our consultant can stay there, and we can hold our meetings there as well.”

I was a little skeptical at first, but he quickly found a nice place that had a two-story outbuilding on 8 acres in a rural, peaceful setting just 15 minutes from our office. It truly was perfect, giving us a quiet space away from the office to work and hash out new ideas for the upcoming year. Plus, it only ran us less than a total of $300, including cleaning fees. Needless to say, I was convinced. We loved it and plan to use it for our future meetings, including our own off-site strategy meetings for upper management. But having the travel bug myself, I started to think about how my wife and I can use Airbnb for our upcoming vacations.


How to Travel and Live for Free

Soon after all of this happened, I took a vacation with my wife to New England to visit the Boston and Cape Cod areas. We had already booked our hotels, but we quickly realized was that we had made a huge mistake. We could have used Airbnb or another similar service and had a much nicer place for about half the money.

I’m not opposed to the concept of renting where you live and renting out what you own, mainly because you have the freedom to move around, while still retaining the benefits of real estate ownership, such as depreciation, mortgage interest, and tax deductions. Who says you have to buy into society’s ideology of working for 30+ years just to own a primary residence in one location that you hope goes up in value?

My mom lived in her primary residence for 45 years and thought the ultimate success was paying that house off. It wasn’t until she reached retirement that she realized it was little help, as she was equity rich and cash poor.

I think one of the biggest point she missed was that she was giving up her freedom of mobility. This is a concept that Millennials seem to grasp much easier than older generations.

Change of Plans

So, as I inch closer and closer to retirement and my vacation home will be paid off this year (which, by the way, sits empty 10 months out of the year), I’m thinking of employing a new strategy. I’ve already downsized out of my big-box primary home since my children are grown, and my wife and I are toying with getting one or two condos or townhouses in a couple of nice locations.

Related: The Top 10 Do’s and Don’ts for Airbnb Short-Stay Landlords

Just as a precaution, we want properties that can carry themselves with regular market rent. After all, you never know what could happen. Then, we want to furnish them nicely and try the Airbnb model. I know this should work very well with my vacation home since it is already set up for short-term rentals and is in a high demand area.

Now, not only will we have three primary residences in retirement, but we can rent them out via an Airbnb type of platform anytime we want. If we want to go to Europe, South America, or a new location, we can do so profitably anytime we want, especially since Airbnb rentals tend to generate more rent than a traditional monthly rental. In other words, we could have total freedom to live wherever and whenever we want anywhere in the world. This is something I’m leaning towards, as I believe it’s not the things that we have in life that are important but the relationships and experiences we get to enjoy.

We’re republishing this article to help out our newer readers.

I would truly love to hear any thoughts from the BiggerPockets community on what you think of this concept or if you’re currently doing something similar.

Be sure to leave your comments below!

About Author

Dave Van Horn

Since 2007, Dave Van Horn has served as president and CEO of PPR The Note Co., a holding company that manages several funds that buy, sell, and hold residential mortgages nationwide. Dave’s expertise is derived from over 30 years of residential and commercial real estate experience as a licensed Realtor, a real estate investor, and a fundraiser. As the latter, Dave has raised over $100 million in both notes and commercial real estate. In addition to his investments and role as CEO, Dave’s biggest passion is to teach others how to share, build, and preserve wealth. He authored Real Estate Note Investing, an introduction to the note investing business, helping investors enter the “other side” of the real estate business.


  1. Bob Ebaugh

    Hi Dave, it’s a great idea! We have a 3BR condo in Medellin Colombia that isn’t a big money maker, but pays the bills there when we are not there. Locally managed, but one of their vehicles for finding clients is AirBnb. Our primary home a bit unique, aboard our boat in St Petersburg. We’ve got a couple more boat trips to take, but then will make our St Pete primary home at one of our current rentals. The issue here is city ordinance prohibits short term rentals in residential zoning areas. It’s not enforced unless there are complaints, but still a “unknown”. But to rent short term when not here would be a significant savings. Might try it regardless, there are many others doing it anyway. Still something to look at if buying with AirBnb in mind.

    • Patricia Sweeney on

      Airbnb is not easy money, it is very labor intensive, landlords must ask, what is my pay rate? Air bnb, owner must be hands on, then there is the washing of laundry, the cleaning of floors, the scrubbing of the kitchen. The extra labor involved is huge, if owner is out of town, then owner has to pay someone who cares to insect property for damage and clean up every time tenants vacate.

  2. We live on a farm, small farming community, 2.5 hrs from Chicago, 1.5 hrs from Madison. We took the nastiest outbuilding on our property and turned it into a little guest house about 13 years ago. We use it when friends, family come visit and we are very involved with couchsurfing and warm showers (where people can travel and host and everything is FREE). In spring of 2015 I decided to see what would happen if I listed it on Airbnb – not expecting much….We are CONSTANTLY booked!!!! Who knew so many people wanted to get away and stay here… We don’t charge as much as I’m sure we could (Airbnb lists it for $75/night), but i’d rather be constantly booked than hosting here and there, maybe once every 6 – 8 months. WHO KNEW! We also seek out odd and unique Airbnb places to stay! Tomorrow night staying i an octagon small shed – bed (which is a Murphy bed that comes over the table when down) and tiny kitchen area and couple stuffed chairs. Complete w/ a compost toilet! If you build it – they will come! Funny, if all these people knew about couchsurfing, they could stay here for no cost. But the majority of people seem to feel more comfortable when they PAY for something (go figure…). As opposed to all our residential rentals, everyone on Airbnb are extremely respectful and leave the place very nice after their stay (way more so than if they stayed in a hotel). Can’t speak more highly about Airbnb.

    • Dave Van Horn

      Thanks for telling your story, Jilly. It’s an interesting insight about the Airbnb tenants being better in a lot of ways vs. your traditional rentals.

      Also, now I’m excited to look for more “unique” spaces like yourself!


  3. Shekeira Ward

    Awesome idea. I have a friend who leased three luxury 1BR apartments in downtown area adjacent to a major concert/sport venue. He pulls in about $4,000 a month OFF EACH APARTMENT off AirBnb while the lease rent for each place is only $1,200 – $1,500. Pretty amazing. Just gotta watch that the apartments doesn’t write a “No Airbnb” clause in the lease! But of course this can be avoided if you own the place.

  4. Mark Pace

    Dave, I had the same idea a few months ago and purchased a property in Gulfport Fl. We are in the process of a high end rehab and have a decorator coming in after the rehab to stage the property. This will be our first Airbnb and if successful I will be doing more in the future.

  5. Rodney D.

    This is a great collection of ideas…

    Ours, was a variation on this theme. As my wife and I approach retirement, we are considering investing in 2 rental properties in a high tourist area and first attempting to vacation rent these via AirBnB for passive income.

    The problem?

    Possible county ordinances which could prohibit rental periods less than 6 months. If a permit doesn’t resolve this, then the fall back would be to rent these out yearly and HOUSE SWAP our home for others in countries we’d like to travel to.

    If we could swap our home for 1 month with another party, say in Spain, then again in Italy, then again in Greece, it would be possible (theoretically) to take a 3 month back-to-back European vacation for the out-of-pocket price of transportation and food.

    Has anyone done this successfully? I know there are international home swap websites out there but don’t know how trustworthy they are.

    • I just swapped my Florida beach vacation rental property for a home in Montreal. I used It was my first experience and the other party had had about 6 previous swaps. We did a simultaneous exchange for two weeks and it worked out splendidly!

      I am thinking of listing my Florida primary property for exchange so I don’t lose the income from the vacation rental. I selected two weeks that are usually slow for the exchange.

      I like the idea of swapping two weeks or more to make it worthwhile. The other party was willing to do a car exchange as well but I needed my car for transportation so we didn’t do that. On the exchange website you can check the reviews of the people you are swapping with and you get a good feel from the communication with the other party.

      My neighbor just spent her entire summer in 3 European countries–all with 3 home exchanges. I will certainly say that it is a great way to travel–unless you would rather be a tourist than a native!

  6. J. Martin

    Hey Dave!
    Thanks for the shout-out, and glad you could make it out to the Summit.
    There were a lot of great ideas shared by yourself and the other awesome speakers.
    Great article! I LOVE Airbnb!

    I get a touch over $3k/mo for my apartment in Oakland on Airbnb, so lots of places in the world are cheaper than that! I just rented it out to go to Hanoi for a while, then rented it again while I went to the Havasupai waterfalls in the Grand Canyon. (got back last night!

    When you can enjoy your life and the world investing in real estate, something’s going right 😉
    Hope to see you again next year out at the SF Bay Summit if not sooner!
    Keep spreading the good word!

    That liability of a primary residence can become

    • Dave Van Horn

      Thanks J. Martin!

      Glad to see another like minded investor utilize the benefits of Airbnb. Hanoi sounds interesting, I’ll definitely have to take a look at your photos!

      Can’t wait for next year’s event, hope so as well!


  7. Amy Ferguson

    Aloha Dave,
    I have been doing vacation rentals in my primary residence for about 6 years. It’s been wonderful way to travel and pay down my mortgage. I just bought a second home in Nevada that isa longterm rental and am getting ready for a 3rd property to do vacation rental here in Kona. I think it’s the way to retire comfortably…

  8. Mark Krupa

    Thanks for the Article!

    I’ve been buying up tiny studios on the European “tourist trail” and making a good return.

    And I can use those apartments which is a lot of fun!

    I have one city that threatened to shut down my “short term rental” so I turned it into a long-term rental.

    My book tells more.

    I enjoy helping others get their Airbnb rental set up.

    Airbnb is good for “buy to let” not just to cover your bills. In one location I make double what a long-term rental could get.

  9. Lynn Wilkinson

    Hi Dave, I am currently renting my 7 bedroom home (privately) to Corporate people and they love being in a “home” atmosphere for dinners, meetings, getting to know others from across the country, running around the local park in the mornings…everything about it seems to satisfy. They pay me a total of $4000. month. I left the house furnished. I got a good deal on a condo nearby, renovated it, and am very happy taking care of 1000 sq. ft. rather than over 3000 sq. ft. This is my first go-round but I think it is wonderful and guess what, the renters are asking what they can do for me! Would I like a 4th bathroom put in down stairs? would I like a solarium on my new condo? Would I like my front driveway done in cement? It is too amazing. They are sooo nice! I think I will have a solarium built on my back deck at the house…I have great views.

  10. Rocky Verteramo

    Hi Dave!
    You can’t go wrong with air bnb and similar sites! First off, the wear and tear is a lot less! I own 3 properties in a college town and 85% of my income for those houses happen in just 8 weekends! They each bring in between 25-35,000/ home. And the beauty of it is I’ve done this for about 10 years w very minimal issues( a scratch on a table here and there) which is less than I would expect! Price matters, obviously. I charge higher than most so I have a higher clientele who respect others property. Price too low like others I know, they get groups of idiots who ruin his place. These sites are great for 2 reasons which is why this will always be my rental game plan as I go into the future and usually all I invest in. 1. It would take me 3-4 monthly rented homes just to make what I make w 1 home in the time I mentioned above, and 2, which you probably knew already, you are aloud by law to rent your primary home out for up to 14 days/year TAX FREE! I do that for my primary home, 6 game rentals + a 2 day graduation weekend, it’s a no brainer for me! I eventually want to branch out and do this with homes in vacation areas where we plan on traveling to often. Good luck with this!

  11. Blair Russell

    Why wait for retirement? Many people are doing this as their main line of work now. It’s so easy to operate Airbnb’s remotely and you just need feet on the ground to handle the day to day stuff. The biggest problem now is that we rent so much we never get there and are too greedy to lay out time for ourselves. Just make sure you watch the number of days you use it for personal use as that can eat into your expenses/tax deductions.

  12. Jerome Mason

    Quick question Dave… I like this idea and it’s something I’ve considered, but my question is- how are you managing the properties and rentals (considering you have multiple homes in various locations)? Do you have a normal property manager for handling keys and check out? I figure it’s easy enough to schedule a maid service when they leave, but I’m thinking how is it handled with the rest? Interested in your reply… and thanks for writing this article. 🙂

    • Dave Van Horn

      Hi Jerome,

      Good question. Others on here with more experience may be able to answer this better than me, but I think you need boots on the ground in some form or the other.

      I’ve also seen keys be handled by lockbox (digital or manual) and even local store/restaurant owners (assuming for a fee) in high density places like NYC.


  13. Andy Thoms

    Love this article as it speaks to my heart and passion. We are full-time Airbnb operators and absolutely love the business and lifestyle. It is amazing to realize you can right size your life and acquire short term rental income producing “assets” in cool destinations, then monetize those assets to create retirement income to off-set your costs to travel and explore the world by hopping from one homesharing community to the next. It’s a beautiful lifestyle full of adventure, or Pura Vida as the Costa Ricans would say. Imagine designing your own full-time lifestyle (right now) around creating quality local authentic experiences for yourself, and others, while earning sustainable income to support retirement, so can enjoy world travel, and adventure, RIGHT NOW. It is very real, and very cool.

  14. I had the same question as Jerome, how do people handle having boots on the ground to deal with the guests., key hand-offs and other tenant matters. Are there property managers that specialize or work with AirBnb rentals.

  15. Teresia Sayler

    I purchased my Airbnb in Maui. They require you have an “on island rep”, which can be a management company or cleaning person, or anyone in between. I asked another Airbnb’er (who’s unit I first stayed at) and the realtor for references for cleaning companies, which I knew I needed and they also have maintenance contacts as well. The keys are simple. You can go with a combo box mounted on/around the door, or even better…I installed a electronic lock that I can generate an access code, email it in a form letter to my guest and never have to worry about keys! It’s awesome! You set the access dates/time as well, so the code expires when they depart. If I have deliveries made there, I can do a one time code, etc. It’s scary to be so far away (on the mainland) but you have to trust and do some homework up front, but it has been well worth it!

  16. Yali Sharon

    Love it Dave! I travel 3-6 months every year and Airbnb my place for double what I pay. Combined with some travel hacking techniques I now break even when I travel and sometimes even profit! (without working of course) Because of this I was able to save enough money that I bought a 3 bed 2 bath in Alhambra and now Airbnb that as well for more than twice the mortgage/tax/insurance. Expenses and vacancies are low so plan on continuing with this strategy until the Airbnb golden age is over…

  17. Nancy Bachety

    We do it this way too and will retire earlier to travel this way too. Two homes so far and the next one on the horizon. It will be a place that makes sense but where we want to spend time too.
    Dave, give us a status update now that it’s a year into your post.

  18. Airbnb by your strategy sounds like a variation on timesharing. This raises a question. Why not acquire instead some inexpensive timeshare resales? They can be swapped through an exchange and rented when not in use. The annual carrying costs on timeshares are often quite reasonable.

  19. Mark Pace

    Hi Dave,

    About 12 months ago we acquired a single family 3/2 home 2 blocks from the beach on the West Coast of Florida. After evaluating the property we decided to try out the vacation rental business with this property. After completing a top to bottom rehab we hired a professional designer to furnish and decorate our property.

    We listed the property on Airbnb and Homeaway. We have been blown away by the first year results. We were booked over 250 nights and have the first half of 2018 almost sold out.

    After getting the business up and running with a reliable cleaning staff we are almost on auto pilot and are looking for a second property to rinse and repeat.

  20. Amber Porter

    There are a couple locations nearer to our home we would love to purchase a property for air bnb. The problem is they just aren’t popular enough locations and other rentals there have a lot of vacancy. Any advice on choosing the best locations or decreasing the vacancy rate?

  21. Paul Doherty

    Most property management companies I’ve spoken to don’t do executive rentals or AirBnB. So how are you managing these when you’re not there, to sign people up, deal with them while there and cleanup when they’re gone?

  22. George Mevawala

    Hey Dave,

    Very interesting article, and glad to hear that you are open to investing in the AIRBNB/ STR model. I have openly invested in short term rental properties in the Scottsdale/ Phoenix market for the last several years, and now own/manage a fleet of 15 successful short term rental properties in the Phoenix market.

    I must say that it has opened many doors for me ( financial freedom), and I have also assisted many of my clients to buy and transition their property into a successful STR property. There are many different strategies with investing in real estate, but the short term rental model stuck to me the most as I always had interest in finding a niche that involved hospitality as well as where you could show off your accomplishments ( I have designed most of my units and definitely would say I am a pride of ownership kind of guy).

    The most important decision with beginning to pick your first investment property for an AIRBNB/ STR property is the location. All of my properties are located 1-2 miles away from local attractions, entertainment, stadiums, etc). We have seen tremendous growth in the Phoenix market in the last 8 years, and I started off by renting out my first property during our peak Spring season and found I could make my entire year mortage in less than 3 months.

    This was enticing and I slowly started to pick up value add opportunities strategically located in the right areas of town and remodel them, furnish them, and then fire them up on the platforms. Off my first full calendar year for my first full time STR property, I managed to maintain a 89% occupancy and gross over 30k off this property. This was considered a homerun to me, and I am very happy to say that i have turned my entire portfolio into very similar results.

    As some of the comments on here have made clear, it is by no means easy.. It is a high level of communication, hospitality, patience, and most important the passion for seeing this venture grow. I now have the pleasure of being able to continue to pick up an additonal 2-3 properties a year, as well as help my clients follow my strategy.

    Feel free to reach out if this is something you are interested in!



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