SunnyDays Vacation Rental Management
A Smart Investor's Guide

Jeff Bosson

Investing in a vacation rental property can be a lucrative endeavor, but only if approached strategically. Many new investors fall into the trap of trying to self-manage their properties while juggling full-time jobs, only to realize that the effort and expertise required can quickly become overwhelming. Understanding the realities of self-management versus professional management can help you make an informed decision and maximize your investment.

At first glance, self-managing a vacation rental may seem like a way to save money. However, the reality is that it requires a significant time commitment, industry knowledge, and the ability to respond to guest needs at all hours. If we break down the typical responsibilities of a self-managing homeowner and the time investment required, we can see that it is not all it’s cracked up to be. Here are the highlights and the time estimates for each:

Guest Communication (7-10 Hours per Week)

Handling guest inquiries, booking requests, and answering questions before, during, and after stays takes considerable time. A single guest interaction may only take a few minutes, but when multiplied by multiple guests and potential guests asking for details, this can easily consume a few hours per week.

Cleaning and Maintenance Coordination (5-8 Hours per Week)

Cleaning between guest stays is crucial for maintaining high reviews and repeat bookings. Even if you hire a professional cleaning service, you must coordinate schedules, inspect the property, and handle any last-minute issues. Maintenance issues, such as a broken appliance or leaky faucet, require immediate attention and can add to the workload. And if you ask any self-manager if they have ever had to jump in when the cleaners didn’t show, or were too late when they had a back to back, you will learn the dirty truth very quickly.

Marketing and Listing Optimization (4-6 Hours per Week)

To stay competitive, vacation rental listings need continuous optimization, most importantly, updating pricing, responding to reviews, and refreshing photos and descriptions. Additionally, marketing the property on multiple platforms and keeping up with seasonal pricing trends require ongoing effort. Many people don’t realize how hard it is to keep calendars over 4 or 5 different listing sites coordinated, but it takes a lot more time than initially thought of.

Accounting and Financial Management (3-5 Hours per Week)

Managing income, expenses, and tax implications for a vacation rental is time-consuming. Many owners struggle with tracking profits, setting aside money for taxes, and ensuring accurate financial reporting. Yes, this needs to be done whether you are self-managing or hire a manager, but when you put all of the other items on top of this one, it can all too naturally get pushed to the side and forgotten about.

Handling Emergencies (Variable, but Often 3-6 Hours per Week)

I call this the “hidden time suck” because not only is it time consuming when something actually happens, most people don’t realize that they are not able to truly enjoy nights out, or vacations because in the back of their minds they are waiting or dreading the next crisis. Guests always have issues that need immediate attention, such as lost keys, HVAC failures, or internet outages. If you are managing the property yourself, you must be available 24/7 to resolve these problems.

Regularly inspecting the property for damage, ensuring inventory like linens and toiletries are well-stocked, and addressing wear and tear is another time-consuming responsibility.

Total Estimated Weekly Time Commitment: 25-39 Hours

For someone with a full-time job, managing a vacation rental can feel like taking on another part-time (or even full-time) job. The result? Increased stress, missed opportunities for optimization, and often a lower return on investment due to lack of industry expertise.

The Benefits of Professional Vacation Rental Management

Many investors hesitate to hire a management company due to perceived costs. However, a well-run management company should not cost you money—it should make you money by maximizing occupancy rates, optimizing pricing strategies, and handling all the operational challenges for you. Here’s how a professional management company adds value:

Higher Revenue Through Dynamic Pricing

A professional manager should use data-driven pricing strategies to adjust nightly rates based on demand, seasonality, and local events. This often results in higher revenue than what a self-managing owner can achieve. A word of warning here, not all managers are created equal in this arena. I for one am not impressed by the software that exists in this space and caution anyone that is letting their management company use only software to set their pricing, we often see it create a race to the bottom and decrease the pricing to an unprofitable level.

Streamlined Operations and Guest Experience

Management companies have dedicated teams to handle guest communications, check-ins, and problem resolution, leading to better reviews and repeat bookings. Happy guests mean higher occupancy and increased profits.

Hassle-Free Maintenance and Housekeeping

A property management company ensures that cleaning and maintenance are handled professionally, preventing last-minute cancellations due to property issues.

Comprehensive Marketing Strategies

With professional photography, listing optimization, and targeted advertising, management companies ensure that your property reaches the right audience and stays competitive in the market.

Financial Transparency and Stress-Free Accounting

A good management company provides detailed financial reports, tracks expenses, and ensures compliance with tax regulations, saving you time and avoiding costly mistakes.

The Right Investment Approach: Self-Management vs. Professional Management

Let’s compare two scenarios:

Scenario 1: Self-Managing Homeowner

• Full-time job + 25-39 hours/week managing the rental

• Struggles with pricing and guest communication

• Stressed about maintenance, cleaning, and emergencies

• Generates $50,000 in rental income but loses time and potential higher earnings due to inefficiencies

Scenario 2: Professional Management

• No additional time commitment from the owner

• Pricing is optimized, marketing is effective, and guest experiences are enhanced

• Increased annual revenue ($60,000-$70,000)

• The management company takes a percentage, but the owner still nets more than if they self-managed

Final Thoughts: Making the Smart Choice

While it’s understandable that some investors hesitate to pay for management services, the right company should increase profitability rather than be seen as an expense. Instead of working an extra part-time job to manage your rental, partnering with a professional team allows you to focus on growing your investment portfolio while enjoying truly passive income.

If you’re considering investing in a vacation rental, the key is to research management companies that align with your financial goals. A great vacation rental investment isn’t just about location—it’s about how efficiently the property is managed to maximize returns. Choose wisely, because your vacation rental investment should work for you, not the other way around.