man with suitcase moving into his short term rental booking

Owning and managing vacation rentals is a dynamic endeavor, one that balances profit, experience, and community impact. Regardless of whether you’re managing a house in Oklahoma City or a condo in San Marcos, CA, you’ll encounter unique challenges specific to different markets. These are hurdles nearly all vacation rental managers have faced, especially in the early days.

However, navigating this terrain requires a careful avoidance of potential pitfalls that can hinder your success. From maintaining a balanced objectivity to perfecting market strategies, ensuring effective communication to building strong relationships with neighbors,

This Redfin article presents a comprehensive list of vital vacation rental issues to sidestep. Drawing on the expertise of industry leaders, you’ll gain valuable insights into these potential roadblocks and learn how to proactively avoid them. You can move onto orchestrating a thriving five-star vacation rental venture, as these experts illuminate the path to smoother operations, satisfied guests, and prosperous outcomes. Learn from their experiences to safeguard your investment, maximize your earnings, and cultivate a positive impact on the hospitality landscape.

man with suitcase moving into his short term rental booking

1. Unbalanced objectivity and emotion

“It’s crucial to remember that your vacation rental is not merely a personal space, but a business asset designed to generate revenue,” recommends Matt Barbuzzi from Park Place Property Management  “While striving to host only the best guests is important, you must be prepared for the occasional mishap, as they’re inevitable in this line of business. Do not allow personal sentiments to cloud your judgment or emotional resilience. This is particularly crucial if your property carries sentimental significance or serves as a family space. Unless you’re renting it to close friends or relatives, we strongly advise against utilizing such properties for short-term rentals due to potential emotional distress.”

2. Neglecting proper screening

“Screening vacation guests presents unique challenges compared to screening conventional yearly renters, as you have limitations on the information you can request, such as contacting and verifying employment history and previous landlords. Nevertheless, implement various techniques to ensure the security of our properties,” shares Maximilian Kostyashkin and Carlos Pena from MAK Realty Group. “These techniques include:

  • Utilizing advanced guest screening software such as Autohost, Chekin, Superego, or Authenticate. These platforms conduct credit checks, background checks, official ID verification, and require damage deposits. Additionally, they provide comprehensive short-term rental agreements for guests to sign.
  • Implementing a minimum stay requirement: During peak seasons, we request a minimum stay of three days. This measure helps prevent individuals from renting your property for a one-time event or party.
  • Noting the usage of noise monitoring technology, which effectively deters party-oriented renters.
  • Employing device monitoring software: All of our properties are equipped with software that tracks the number of devices in use. A sudden spike in device count, such as reaching 20, is often indicative of a potential party being hosted by your guests.”

3. Underpaying housekeeping

“Don’t settle for the lowest cost – invest in your cleaners, and your guests will undoubtedly notice the difference in the quality of your vacation rental,” stresses Realty Street.

“I can’t stress enough how crucial it is to pay cleaners. By offering fair compensation, you not only maintain a high standard of cleanliness but also enhance their motivation and dedication to delivering exceptional service. Skilled cleaners are attracted to good pay, and this directly impacts the guest experience, contributing to a positive reputation, and ensuring a comfortable and welcoming environment for your guests.”

4. Overcomplicating your guest’s experience 

“Don’t impose excessive check-out procedures on guests. Tasks such as initiating a load of towels, disposing of kitchen trash, and running the dishwasher are optimal. It’s essential to communicate to guests that these chores contribute to minimizing cleaning fees and encouraging early check-ins,” says HAVEN Property Management.

“Offer instructional videos for any intricate features in your vacation rental. Videos that guide guests through operating the hot tub, using smart devices, or navigating other complex equipment can be conveniently provided in video format.”

5. Setting bad pricing

“Many hosts lack market knowledge about rates and set their prices based on their emotional attachment to the specific property. This often leads to rates that are excessively high for the market, resulting in a lack of bookings,” shares Oliver Albrecht from Valibera. “Then after a while, they significantly reduce the rates, leading to more bookings, but these rates may only cover the house’s costs without generating any profit for the homeowners. This cycle continues for a while until they eventually give up, having to either rent the house on a long-term basis or even sell it due to their inability to meet the mortgage payments.”

family enjoying the backyard in the vacation rental for the eek

6. Communication problems

“The foremost error in vacation rental management is failing to communicate with property owners. Their investment properties, often among their most valuable assets, rely on generating income or covering their costs,” says Port Aransas Airbnb Vacation Rental Property Management by Grand Welcome

“Entrusting management to others necessitates trust, and trust thrives on communication. Without it, owners concoct narratives, eroding trust, leading to misunderstandings and unfulfilled expectations. Communication is the bedrock of vacation rental partnerships, ensuring both parties thrive. A proactive approach, balancing issues and successes, fosters deeper trust. Regular, strategic personal calls build trust, deepen partnerships, and facilitate owner-to-owner referrals that surpass marketing efforts in expanding business.”

7. Having a bad relationship with your neighbors 

“Some owners become concerned about potentially upsetting neighbors with their short-term rental (STR) properties, and rightfully so—no one wants to create adversaries,” recommends Long Beach Airbnb Vacation Rental Property Management by Grand Welcome.

“Provide owners with the following anti-nuisance tactics:

  • Communicate with the neighbors before launching your short term rental (STR) and provide them with a contact number to call if any issues arise.
  • Be available 24/7 for communication or property visits to ensure a peaceful environment.
  • Communicate with guests—through the listing, pre-arrival emails, and arrival-day texts—that events and parties are prohibited, and violating this rule will result in eviction. Be polite but firm.
  • Consider only renting to guests who stay for more than two nights (three or more nights are even better). One-night stays tend to attract “party” people.

Here is an example from a standard email I send to my STR guests:

I wanted to let you know that there is a long-term tenant living above the garage (separate building) and neighbors on both sides in close proximity, which means the back patio closes at 11pm sharp. The Belmont Heights Retreat is the perfect place for peace and serenity.  

If you have any issues during business hours – my contact information can be found below, and we have a Guest Services line available 24/7 at 888.XXX.XXXX”

8. Neglecting feedback 

“Feedback is the lifeblood of your vacation rental. How do you know what guests do or don’t like, or where you’re missing the mark on certain things? Without actively seeking, tracking, and implementing feedback, you’re vulnerable to operational blind spots that will impact your bottom line,” suggests Michael Skinner from Savvy VRM. “If guests don’t leave a review, nudge them by politely asking for one. Or send them a text asking if they’d be open to discussing their experience with you on a quick phone call.”

9. Poor market strategy

“At Grand Welcome Nashville, we don’t just rely on traditional platforms. We amplify our reach by promoting on over 120+ websites, social media marketing campaigns, and our community ensuring our homeowners get unparalleled exposure and guests taste authentic Nashville,” suggests Nashville Airbnb Rental Property Management by Grand Welcome.

Nashville is more than just a city; it’s an experience, a melody that lingers long after the song ends. I think that capturing this essence in your marketing is crucial. Highlighting local attractions, events, and the unique Nashville vibe can magnetize guests, drawing them into the city’s embrace.”

10. Skimping on professional photos

“I believe the top mistake to avoid is not hiring a professional photographer to take listing photos. This can differentiate you from your competition and make you stand out instantly, as first impressions are incredibly important,” recommends Gabe Chase from Brentwood Property Group.

women in a well lit rented room

11. “Set it and forget it” pricing

“One of the most common mistakes is adopting the ‘set it and forget it’ approach to pricing. Each day holds its distinct market value, and overlooking this fact can result in either foregoing potential income or struggling to secure bookings,” says Garret Ham from Weekender Management. “While using pricing tools like Wheelhouse and PriceLabs is a positive step, they are not a universal solution. These tools still rely on the property manager’s insights and knowledge, and should be complemented by your own market research.”

12. Unclear check-in, check-out times

“It’s good to remind the guest in a friendly way what time check-out is, especially the day before to check-out. Also, place it in a visible space in the house and in a friendly ‘hope you liked your trip’ text,” suggests Michael B. Emerick, Co-Founder of Oversee. “If the guest gets a little spacey and leaves late, it can cause a poor experience for the next guest by pushing back their check-in time. Be as hospitable as possible, but don’t let a guest infringe upon another guest’s vacation.”

13. Lack of adequate property insurance

“Not having property insurance leaves vacation rental owners vulnerable to potential financial losses and liabilities in the event of accidents, damages, or unforeseen circumstances,” warns  Nomadness Rentals. “Proper insurance coverage, such as vacation rental insurance, is crucial to safeguarding your investment and protecting against risks associated with short-term rentals.”

14. Not setting house rules and policies for guests

“Whether it’s a chic apartment in the heart of Austin or a secluded cabin in Hill Country, clarity is key. Clearly defined house rules, from pet policies to quiet hours, ensure guests know what’s expected,” recommends Alexander Buchanan, owner of Austin Airbnb Rental Property Management by Grand Welcome. “A comprehensive guest manual, with guidelines on appliance usage, emergency contacts, and local tips, ensures a hassle-free stay. This proactive approach minimizes misunderstandings and ensures guests can fully relax, knowing they’re in good hands.”

15. Incapable of juggling roles and meeting demands

“As vacation rental managers, we wear many hats, skillfully handling both property owners and their assets – encompassing furnishing, maintenance, upkeep, updates, pricing, marketing/advertising, accounting, and more,” says Blue Pacific Vacation Rentals

“We also navigate the world of guests – marketing/advertising to secure bookings, administering paperwork/contracts for owner and guest protection, overseeing maintenance, managing access/technology/information, arranging cleaning/maintenance, and meticulously curating guest experiences to foster repeat patronage, among other responsibilities. This multifaceted role underscores the distinct and demanding nature of vacation rental management, far exceeding the misconception that it merely involves posting property images on Airbnb.”

“There are myriad mistakes one can make while managing a short-term rental venture. Drawing from my experience in the current market, the most prevalent errors involve not assigning sufficient importance to gaining a competitive edge. This entails investing in elements such as furnishing, decorations, high-quality linens, bedding, and amenities, all of which are essential in an already saturated market. 

family on deck of vacation rental toasting

16. Not differentiating yourself

“It’s imperative to set yourself apart amidst this crowded landscape,” suggests Tampa Airbnb Vacation Rental Property Management by Grand Welcome. “Furthermore, the significance of a well-planned pricing strategy, maintaining cleanliness, and ensuring effective communication and responsiveness in guest services cannot be overlooked in terms of common mistakes. 

Make sure to differentiate yourself. With numerous short-term rentals available, standing out is crucial. Highlight what makes your property unique, whether it’s a specific theme, design, or location. Don’t ignore offering local insights. As a host, you can provide valuable insights about the local area. Recommendations for nearby attractions, restaurants, and services can enhance the guest experience.”

17. Skipping local laws and regulations

“Begin by thoroughly studying the local laws and regulations that pertain to STRs,” recommends MyTripify. “Ensure you grasp all the pertinent regulations, or enlist the expertise of a property manager who does. Non-compliance, such as violating HOA restrictions or listing an STR with an occupancy exceeding septic tank limits, can lead to hefty fines. The potential consequences far outweigh any initial gains.

That being said, don’t underestimate the importance of insurance coverage for STR hosts. Investing in insurance products is a cost-effective means of mitigating the risk of property damage. By securing insurance, you regain control over potential damages and maintain your property’s excellent condition, all the while upholding high levels of guest satisfaction.”

18. Forgetting systems and setting expectations as you grow your business

One of the biggest mistakes vacation rental managers make that’s costing you time and money is hiring additional people on your team without systems,” warns Pink Cash Cow Property Management. “As your business grows, you can’t do everything yourself, so you hire someone to help you with tasks at the property or remotely. However, the person may not do it right, not getting the results you’re looking for, or you’re getting negative reviews and guest complaints. 

You end up doing the work again yourself or spending time trying to find someone else. The best way to efficiently operate and grow your business without taking more time or effort is creating systems and processes that people can follow for consistent results, like getting five-star reviews without you doing the work. Have a process and system for maintenance, cleaning, staging, linens, etc.”

19. Not being persistent enough 

“One of the most, if not the most, important steps in ensuring successful vacation management for your home or business is to ensure that you are overly communicative with your guests, both before and during their stay,” shares Emily Bishop, Communications Manager for Brightwild. “Lay out check-in instructions clearly, while also making sure that any preemptive questions guests may have are already answered. It seems overly simplistic, but you’d be surprised to know that this isn’t always a priority for some vacation management companies.”

20. Not learning and resolving problems quickly

“One observation I make regarding most vacation rentals is the absence of established, repeatable systems geared towards success. This translates to encountering hard challenges, even if these issues were addressed just six months prior. Consequently, the team finds itself retracing steps to unearth solutions for guests or risk leaving them discontented,” says Cody Wood from STR Accommodations.

“Similarly, another prevailing issue frequently encountered in the vacation rental industry pertains to the swiftness with which guest concerns are tackled. At times, these concerns revolve around maintenance matters, indicating a deficiency in the property’s upkeep schedule, or worse, its nonexistence. 

Alternatively, the problems might stem from malfunctioning amenities or depleted supplies due to a lack of efficient restocking systems on the part of the owner or manager. The remedy for both aforementioned concerns involves implementing a quarterly or monthly maintenance regimen supplemented by a 24/7 emergency helpline dedicated to property support. Diligent tracking of inventory levels post each turnover clean at the property level is essential. Speed assumes paramount importance in the realm of vacation rentals, as our physical absence from the property necessitates possessing a clear grasp of effective troubleshooting procedures. This approach not only facilitates swift responses but also leaves guests content with the prompt resolution of their issues.”

21. Keeping up with maintenance needs

“One common mistake is underestimating the ongoing maintenance needs of a vacation rental property. Failing to address maintenance issues promptly can lead to negative reviews and dissatisfied guests,Bend Airbnb Vacation Rental Property Management by Grand Welcome advises. “To avoid this, we recommend creating a thorough maintenance schedule, conduct regular inspections, and request that the homeowner set aside a portion of their rental income for unforeseen repairs.

Sameway, using poor-quality or outdated photos for your vacation rental property can deter potential guests. Ignoring the importance of professional photography can lead to decreased bookings and interest. We highly recommend investing in high-quality, well-lit photos that accurately showcase the property’s best features. Always hire a professional photographer who specializes in real estate to capture the property’s appeal.”

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Mike McNamara

Mike McNamara

A Las Vegas Realtor since 2008. Mike has a wide range of knowledge around all things Las Vegas.

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