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A Path to Retirement for Active Career People Using Short-Term-Rental

Do you dream of a retirement under the sun? Is there any lifestyle you really find appealing for after you retire from the workforce? If so, as it is often the case, this could become possible but only provided a sound management early in your career.

I will expose a possible solution-path to have you reach your retirement objectives here.

The Problem

In first-world nations, the path towards a comfortable retirement, without too many jurisdiction constraints such as healthcare coverage linked to a presence in stated jurisdiction, is evolving to an always more difficult one over time.

Revenue that is also available during retirement itself is also typically widely insufficient to initiate a retirement project, but it is rather more adequate to a limited subsistance revenue.

Generating sideline revenue in first-world economies is also becoming a challenge as interest rates are low and barrier to entry in many markets an uphill battle against permits, lawsuits and other constraints that keep accumulating over the years. In short, retiring is becoming more and more difficult.

Solution Overview

I do not pretend to present to you the Holly-Grail of retirement here – as no one solution fits all – yet, I will present a realistic and feasible path for some people.

These people that could benefit from my advice have the following in common:

  • They appreciate travel.
  • Have some income to play with to allocate to a project.
  • Are disciplined and focus to a reasonable extent.

Step 1: Using equity or savings for your retirement project

There is no miracle here, any project requires resources. This step is on your lap to realize, yet be comforted that it is not of unmanageable magnitude. Often, there is enough equity into your primary home for which you’ve pais a mortgage throughout the years for you to convert such equity into cash. You are the one who knows where and how to acquire such minimalist liquidity so I will not expand on this.

Step 2: Conceptualize your retirement conditions you desire

What are the conditions that are appealing to you for your retirement? Does it involve a beach and a caressing sun? Is it rather the fresh air of the mountains that better resumes your desires? Or, do you see yourself golfing and boating in alternance daily?

Once again, only you, as an individual or as a couple, know what your retirement goals are in term of lifestyle. Define them as clearly as possible, and abstract the immediate difficulties to reach those goals for now.

Step 3: Locate a retirement spot

The dreaming phase of your retirement project is now done with. Now, you have to manage your project coldly and rationally.

As a matter of fact, do not locate a single retirement spot, but rather many. Later on, we will need to cross-reference each candidate location with other parameters and contraints. Nevertheless, browse through properties on this website, or pick your next vacation spot based on your feelings to survey the location.

Step 4: Cross-reference candidate locations with services

Any good retirement location should have some specific availability of good and services around it.

  • Healthcare facilities.
  • Secure environment.
  • Internet and communications infrastructure.
  • Reliability in energy source.

But, you should expand the cross-reference of your candidate locations considerations to Short-Term-Rental necessities.

  • Proximity of an airport with many flights daily.
  • Hotels with high-occupancy rates.
  • Hands-off legislative environment allowing Short-Term-Rentals to thrive.

Should you be able to identify a location that respects your own retirement goals as well as Short-Term-Rental necessities, you may have hit the jack-pot for your plan.

Step 5: Locate and acquire a property in your retirement spot

With your equity or cash at hand, you will become able to lock-in the purchase of a property corresponding to your long-time goals in terms of location. You may not need a significant down-payment and prices for properties abroad are often lower than into first-world markets. Assuming a 10% to 20% down-payment, you may require as little as $20,000 down to lock-in your purchase. Go for it. Surround yourself with a real-estate agent you trust, and acquire your property.

Step 6: Operate your property as a Short-Term-Rental for the years to follow

These locations that are Short-Term-Rental friendly are full of Management Services that can operate your property without generating you issues difficult to resolve remotely. Indeed, they may keep 30% of the rental income, and that hurts when looking at this from that angle. But, over time, if your property pays for itself through the remaining 70% of rental income, your return on investment will grow get you a retirement property for your down-payment alone.

Last step: Kick these people out, this is your home now

When your retirement time comes, stop these Short-Term-Rental activities and become your own guest into your property. Live your dreams as much as you can as you deserve it!


I have seen this plan executed well hundreds of times, and I always feel proud when I finally see a couple retaking possession of their property when their retirement time comes. It is fulfilling to know people that had enough creativity and confidence to draw their own paths toward a retirement of their choosing and succeed. I, myself, was most interested in a mountain living lifestyle than anything else. I ended-up living in Jarabacoa, in the middle of the Hispaniola island in the Dominican-Republic. My surroundings are closer to a Switzerland postal-card than the typical image of a Caribbean sea that people relate to the Dominican-Republic. This is to show that it can happen the settings of your dream retirement are not that easy to reach, and surrounding yourself with the right people that can point you out in the right direction can make a difference in the outcome. We are here to help you with your retirement project if you want. Get in touch with us at [email protected] and talk to us about it. There is potentially a spot that is perfect for your project that we’d like you to know about.

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