Updated : May 14, 2025
As a vacation rental manager, you’ll juggle various property management challenges, such as coordinating cleaners, updating calendars, managing double bookings, providing quick guest support, and handling seasonal volatility. Every missed message, scheduling error, or empty off-season week hits your bottom line.
In this guide, we’ll address the real vacation rental property management issues that keep property managers up at night and suggest practical solutions and tools to solve all your STR management hurdles.
When you manage a large portfolio, your property management business will encounter many hiccups. Knowing some of those challenges and having a system set up to tackle them will ensure more streamlined operations and maximized revenue.
1. Regular Property Upkeep & Repair
Minor issues like a leaky faucet or a broken AC can quickly become expensive headaches if left unchecked. Worse, maintenance failures impact guest satisfaction and future bookings.
How to stay proactive:
- Follow a preventive maintenance plan rather than reacting to problems.
- Set aside 5–10% of monthly rental income for unexpected repairs.
- Use AI for vacation rentals to automate repetitive maintenance tasks.
- Build a network of local contractors: plumbers, electricians, handymen, and cleaners before peak season hits.
As Daniel Zammata, a seasoned property manager, states,
“Having spent over a decade immersed in property management, I’ve learned that preventive maintenance isn’t just a best practice—it’s the cornerstone of long-term success. Staying ahead of potential issues saves time and money and builds trust with tenants and property owners alike.”
Last but not least, follow a thorough cleaning and maintenance routine. You can follow a detailed checklist for your property management business. However, here’s a quick checklist:
- Inspect plumbing for leaks under sinks/toilets.
- Examine grout/caulk in bathrooms for mold or cracks
- Service HVAC systems before peak usage.
- Test smoke detectors, CO monitors, and fire extinguishers.
- Examine grout/caulk in bathrooms for mold or cracks.
- Clear gutters and check roofs for damage.
- Deep-clean and repair faulty appliances.
- Schedule pest control treatments.
- Mow the lawn and trim shrubs in the garden.
2. Hiring & Coordination with Maintenance Staff
Finding good maintenance staff is tough, especially during peak demand spikes. You don’t want to scramble to fix an urgent repair hours before new guests arrive.
For example, heating systems and snow-related issues increase during the high season for mountain cabins.
How to build a dependable team:
- Identify the services your property needs, e.g, plumbing, deep cleaning, snow removal for cabins.
- Vet contractors during the off-season when they’re less busy so that you have a competent staff to help you when your property is brimming with guests.
Here’s a fantastic idea by an STR host on Reddit to find and onboard a good cleaning team.
“I contacted cleaners in my area to bring their crew during the slow season to assist with a deep clean. That way, I could see how they manage staff, organize cleaning, and know what to clean and how. I invited 3 crews, but the second crew was exactly what I needed. I then asked if they would take on the property and asked them to name their price. They did, the price was too low, I told her to first do a few cleans before giving a price, and I would pay by the hour for now. Once they had a better idea of the time required, we went over a few things that I wanted done a bit differently, and I increased the price to be more than asked for, explaining I want to pay well so my place stays high priority.”
After you set up standard operating procedures (SOPs), the next step is to optimize the cleaning schedule for quick turnovers. You must regularly communicate with your maintenance staff and guests to avoid scheduling clashes, especially if you manage multiple vacation rentals.
To make this easier, consider using apps like Breezeway. Such tools let you auto-assign tasks and track progress from one dashboard.
3. Promptly Responding to Guests
Today’s guests expect fast answers even late at night. Delays in communication is one of the most common property management challenges and often lead to poor reviews, canceled stays, and lost repeat business. Responding to messages from staying and booking guests within minutes is hard to imagine.
How to respond without burning out:
- Use a centralized inbox or a property management system to manage Airbnb, Vrbo, Booking.com, and direct inquiries in one place.
- Set clear expectations about your communication hours when guests book.
An Airbnb user suggests specifying your communication method and availability upfront to avoid late-night issues.
If you want to automate common responses, use property management tools like Hostfully or Hospitable. These platforms act as centralized inboxes that instantly answer last-minute guest queries or concerns raised by your guests from across all the OTA platforms on your behalf. So, no need to lose your sleep for late-night guest messages.
A property manager echoes this on a Reddit thread,
“Our channel manager auto-sends reminders and door codes and updates to the guests, updates the calendars, and sends notifications to the cleaners.“
4. Handling Guest Expectations
Many issues stem from misaligned expectations. Guests often imagine properties to be more luxurious or equipped than they really are unless you clearly state this.
How to optimize Airbnb listing to deal with this:
- Avoid misunderstandings by mailing a downloadable manual of rules, amenities, notes, and an expectations checklist 72 hours before they arrive at your place.
- Add all the information about terms of service to your listing so guests have no over-expectations.
- Keeping your Airbnb listing description accurate, detailed, and up-to-date reduces confusion regarding included amenities. This will help potential guests make informed decisions.
- Share your Airbnb welcome book after guests check in.
Here’s a perfect example of a detailed description, instructions, and expectations on an Airbnb listing.
5. Guest Misbehavior & Non-compliance with Property Policies
Unauthorized parties, noise complaints, pet rule violations — they happen. Ignoring bad behavior can lead to HOA fines, bad reviews, or even being delisted by your OTA. This is one of the most common and tedious property management challenges.
How to enforce rules effectively:
- Enrol properties in AirCover damage protection for Hosts for protection against damages.
- Install outdoor cameras or smart doorbells to monitor guest flow while respecting privacy laws. This recorded data also serves as indisputable evidence if policy violations occur.
- Set clear rules in writing and reiterate them post-booking.
- Ask your maintenance staff to click pictures or shoot videos of the entire property before guest arrival, which you can use to claim reimbursement for any damages.
Lydia Patel has had similar strange experiences with her Airbnb listings, and she offers excellent advice for handling such situations. One guest requested to check in 16 hours earlier than scheduled, which is one night extra. She shares her insights on her YouTube channel.
“I could change the reservation to reflect the correct dates, and Airbnb sends it back to the guests that you edited the reservation… the cost for an extra night automatically adjusts.”
The same guest also arrived at the property with an unannounced pet, so Patel sent him a gentle reminder text for an additional Airbnb cleaning fee:
“Hey, I noticed you have a dog. We do charge a pet fee, it’s X number of dollars.”
If nothing works out, she recommends escalating the issue to Airbnb “to get this covered under the Aircover protection policy.”
6. Safety Concerns
Safety concerns can put guests at risk, lead to lawsuits, and harm your reputation. Guests need to feel secure in your vacation rental, and theft can upset hosts and guests. Handling these property management challenges increases your credibility among guests and property owners.
How to boost guest safety:
- Install smart locks and motion-activated lighting at all entrances.
- Regularly test CO2 detectors, smoke alarms, and fire extinguishers.
- Provide a visible first aid kit and emergency contacts list inside the property.
A well-lit, secure property reassures guests and sets you apart from careless competitors.
7. Optimizing Strategies for Multi-channel Distribution
Listing your vacation rental across multiple OTAs like Airbnb, Vrbo, and Booking.com is essential for maximizing visibility and bookings. But it also creates a new layer of complexity.
Each platform has its own algorithms, listing rules, and pricing structures. What works for one OTA won’t necessarily work for another. Without a clear multi-channel distribution strategy, managing your portfolio can become overwhelming really fast.
Two major risks stand out:
- Revenue loss from poor pricing adjustments.
- Double bookings that damage your reputation and penalize your listings.
Fortunately, technology can help you stay ahead.
For smarter pricing and performance tracking:
The PriceLabs Portfolio Analytics tool lets you monitor key KPIs like average daily rate (ADR), revenue per available room (RevPAR), and occupancy rate across your entire portfolio from a single PriceLabs market dashboard. You can quickly adjust strategies for underperforming listings without guessing with real-time market insights and revenue charts.
For preventing double bookings and calendar chaos:
Double booking is a common issue when listing your STR home on multiple OTA platforms. Guests often feel frustrated when their reservation is canceled, leading to negative reviews and potential penalties for you. To prevent this, invest in a channel manager like Guesty, Lighthouse, or Lodgify. These tools sync your booking calendar into one dashboard, removing the risk of double bookings.
8. Drop in Occupancy Rates During Non-peak Season
Seasonal dips in bookings are one of the biggest property management challenges. Whether you manage a beachfront luxury villa or a cozy lakeside cabin, off-peak months can leave your calendar looking empty. This vacation rental issue is the same for all PMs in every location.
The good news is that smart pricing and targeted offers can help you stay profitable even during the slowest times of year.
Here’s how to keep guests coming in when short-term rental bookings are low:
Use dynamic pricing to stay competitive
Tools like PriceLabs Dynamic Pricing software automatically adjust your nightly rates based on seasonality, historical data, future market trends, and competitor pricing. Instead of manually tweaking prices or guessing, you’ll always stay aligned with what guests will pay.
Plan off-season marketing early
You don’t have to accept empty calendars during the off-season. You can turn quieter months into consistent revenue streams with dynamic pricing and strategic perks.
Knowing future pricing patterns in advance makes it easier to create special promotions, social media marketing campaigns, and email campaigns targeting slower periods.
A property management company, The Blue Kite, improved occupancy rates by 20% during the low season by adjusting rates dynamically with PriceLabs and offering long-stay incentives for digital nomads.
Offer irresistible off-season packages
Travelers still book off-peak if the value is clear. Think:
- Complimentary breakfast baskets
- Reduced cleaning fees
- Free late check-outs
- Market as proximity to vacation rental major local events
- Discounted weekend getaway packages
- Adding business amenities like dedicated workspaces and fast Wi-Fi for remote workers
Also Read: Airbnb Promotion Guide to get more bookings.
9. Collecting & Managing Guest Reviews
Guest reviews are critical to building credibility, ranking higher on OTAs, and securing future bookings. Yet, many property managers struggle either with low review rates or the occasional negative feedback that can damage a property’s reputation.
However, managing reviews can be more controllable than it seems if you set the right systems in place.
Here’s how to boost positive reviews and protect your brand:
Make it effortless to leave feedback
Send a friendly post-stay email or SMS with a direct link to your review platform. Timing matters, so follow up within 24 hours of check-out when the stay is still fresh in their minds.
Incentivize the review process
Offer a small reward, like a shopping coupon or a 15% discount on a future stay, to encourage guests to share their experience. Many travelers need a little extra motivation.
Address negative feedback professionally
Respond quickly and politely if a guest leaves a less-than-stellar review on Airbnb. Acknowledge the issue, explain how you will address it, and show empathy. Future guests pay close attention to how hosts handle problems. A thoughtful reply can often outweigh a nasty comment.
A host echoes this sentiment:
“Make sure you clearly communicate with guests that you want private feedback on items needing maintenance or improvement.”
This simple proactive step can dramatically increase your 5-star review rates.
10. Keeping Up with Local Regulations
STR regulations vary by country, state, city, and even neighborhood. Depending on location, licensing rules, tax obligations, property standards, and rental caps can differ wildly. The complexity only increases if you operate properties across multiple cities or states.
Managing compliance isn’t just a formality. Failing to comply with local laws can lead to fines, penalties, listing suspensions, and legal disputes with neighbors, cities, or HOAs
How to stay compliant:
Hire a local legal expert
Working with a real estate attorney or STR compliance consultant ensures that your contracts, permits, insurance, and tax filings are always up to date. An annual legal audit can catch small mistakes before they become costly problems.
Stay informed through official channels
Subscribe to city newsletters, attend community meetings, and monitor tourism board updates where your rentals are located. Many cities announce changes months in advance — but it’s up to you to stay ahead.
Document everything
Keep digital copies of all permits, business licenses, and communication with local authorities. Organized records make it easier to prove compliance if your property is ever challenged.
FAQs
1. What’s a property manager’s greatest responsibility?
Smooth STR operation, maintenance, and improving revenue are the core responsibilities of the vacation rental manager.
2. What is a SWOT analysis for property management?
Property managers use SWOT analysis to identify internal strengths and weaknesses, external opportunities and threats.
3. What makes a property manager stand out?
An exceptional property manager has strong communication, problem-solving, organizational, and analytical skills.
Final Words: From Reactive to Proactive Management
Vacation rental management will always come with property management challenges, but how you handle them defines your success. You can turn common hurdles into new revenue opportunities with a proactive strategy, the right tools, and innovative operational systems.
Every solution you implement today, from preventive maintenance plans to more innovative pricing strategies, moves your business closer to smoother operations, better guest experiences, and stronger profitability.
