By a Concerned Jamaican Realtor
There’s an uncomfortable conversation many in the Jamaican real estate and property management space have been avoiding—particularly those of us who wear multiple hats. As a full-time realtor who once agreed to manage a short-term rental on behalf of an overseas client, I’ve reached a point where I feel compelled to share what I’ve learned—candidly, and without names attached.
I hope this letter offers a balanced perspective to both realtors and overseas property owners trying to make Airbnb work in today’s evolving Jamaican market.
When Good Intentions Meet Harsh Realities
Not long ago, I agreed to manage a furnished apartment for someone based abroad. The arrangement started with the best of intentions: the owner trusted me, I knew the market well, and it seemed like a mutually beneficial partnership. They saw the apartment as a kind of retirement plan—something that could generate semi-passive income through short-term rentals, while also preserving the value of the asset.
But within a matter of months, the cracks began to show. The truth is, managing an Airbnb—or any short-term rental—is not a passive exercise. It is a full-time hospitality operation disguised as real estate. Guest communication, cleaning schedules, maintenance calls, platform updates, emergency responses, refund disputes, accounting—these aren’t occasional tasks. They are daily demands.
Worse still, the short-term rental market in Jamaica is now heavily saturated. The number of listings has exploded, particularly in popular tourist areas. Even well-located properties with solid amenities are struggling to maintain occupancy. Travelers today are spoiled for choice, and they often gravitate toward hosts with hundreds of five-star reviews, professional photos, concierge services, and instant communication. Unless you’re operating at that level—or employing someone who is—it’s hard to stand out.
The apartment I managed was nice, but it was one of many similar units in a crowded field. We had sporadic bookings, limited repeat guests, and constant pressure to lower prices to remain competitive. Eventually, the stress of daily operations—combined with the need to focus on my commission-only real estate business—led me to the inevitable decision: I could no longer manage the unit.
A Word to Realtors
To my fellow realtors, especially those newer to the profession or those trying to offer “value-added” services: be cautious about taking on property management for short-term rentals—especially on your own. Unless you have a team (cleaners, maintenance contacts, reliable admin support), you're setting yourself up for burnout.
What begins as a favour to a client or friend can quickly spiral into a part-time job that conflicts with your actual livelihood. Your real estate career, if done right, already demands high energy, responsiveness, and focus. Adding Airbnb hosting—without support or proper compensation—can distract you from the bigger picture. You're not doing anyone a favour if you’re stretched thin and unable to give either role the attention it requires.
A Message for Property Owners Abroad
For those living overseas and relying on someone “back home” to manage your investment, I urge you to approach short-term rental management with eyes wide open. Many owners assume their property will “just rent itself” on Airbnb or Booking.com, but this isn’t 2015 anymore. Today’s guest is more discerning, and the market is far more competitive.
Short-term rentals require:
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Professional cleaning between every guest
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24/7 communication for booking inquiries and guest issues
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Ongoing maintenance and immediate troubleshooting
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Frequent supply restocking
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Careful tax and financial reporting
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An active host account with a strong review history
If your local contact can’t commit to these responsibilities—or doesn’t have the time or systems in place—you’re not setting them up for success. And remember: if your Airbnb account isn’t in your name, then you don’t control the reviews, the payouts, or the brand. It’s your investment—own it.
You might find, as I’ve come to recommend, that a long-term rental arrangement is a more stable option. While it doesn’t offer the highs of nightly rates, it does provide predictable income, fewer moving parts, and the ability to plan upgrades methodically.
A Hard Truth
The final straw for me came when a guest on a major booking platform stole mats and towels. Yes, it happens. And no, not all platforms offer hosts insurance. Between damages, theft, and wear and tear, the financial risk of short-term guests is real. Without the protections of a full-time management structure—or at least a vetted team—it’s just not sustainable.
Even if the bookings were more frequent, the administrative burden and potential tax complications made it clear that this wasn’t a long-term solution I could justify. I had to protect my time, my energy, and my primary business. I stepped away, transferred the account, and returned the keys with full transparency and professionalism.
The Takeaway
If you’re a realtor, focus on what you do best: selling, renting, and guiding people through life-changing property decisions. If you’re a property owner, don’t assume that short-term rental income is easy, or that anyone on the ground can manage it casually. It’s a business—and like any business, it needs a plan, a team, and accountability.
This isn’t to say Airbnb doesn’t have its place. It absolutely can be lucrative with the right setup. But don’t chase potential without confronting the practicalities.
Let’s move toward more honest conversations in our industry—less about hype and more about clarity.
Sincerely,
A Concerned Realtor in Jamaica