What to Consider about Short Term Real Estate in 2024

Estimated reading time: 20 minutes

Embarking on a journey in real estate investment can be akin to navigating a vast and complex landscape. There’s no one-size-fits-all approach, and for prospective investors, the choice of asset class is often a daunting decision.

I, too, initiated my real estate journey in multifamily real estate syndications, a popular choice among real estate investors. However, as I delved deeper into the realm of real estate, I discovered the allure of diversification, especially concerning rental income.

Short-term rentals (STRs), also known as vacation rentals, emerged as an intriguing avenue. In the contest between STRs and long-term rentals (LTRs), the former often boasts a significant advantage in terms of cash flow. It’s not uncommon for STRs to yield nearly double the income compared to their LTR counterparts.

Let’s delve into the intricacies of STRs and explore why they have become an attractive prospect for both individual property owners and more extensive investment entities such as funds.

Unlocking the World of Short-Term Rentals

At its core, a property qualifies as a short-term rental (STR) if it is rented for an average duration of less than seven days. These properties, frequently labeled as vacation rentals, cater to individuals on leisure or business travelers.

In our digital age, platforms like Airbnb and VRBO have made it incredibly accessible for anyone with a vacation home or rental property to venture into the realm of short-term rentals. The flexibility of STRs allows property owners to maximize earnings by:

  1. Charging higher rates.
  2. Swiftly turning over the property for more renters.

This flexibility has contributed to the phenomenon observed in locations like New York, where the number of Airbnb listings surpasses available apartments for long-term rental.

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Comparing STRs and LTRs: A Tale of Income Streams

The choice between STRs and LTRs is a crucial decision for real estate investors, and it often hinges on the desired income stream. Long-term rentals offer a more predictable income, with leases typically signed for a year, providing stability for landlords to budget and secure financing.

On the contrary, the income from short-term rentals tends to be more erratic, influenced by factors like nearby competition, seasonality, average guest stays, and the average daily rate (ADR). Yet, the potential upside is significant, as evidenced by data from STR research firm AirDNA, reporting a record average annual revenue of $56,000 for full-time STRs in 2021.

Financing the Venture: LTRs vs. STRs

The financing landscape differs significantly when considering LTRs and STRs. Long-term rentals, backed by longer leases and a more consistent income stream, often find it easier to secure financing. Additionally, they can benefit from more competitive interest rates and lower down payments.

Conversely, financing STRs through traditional or conventional loans might pose challenges due to stringent lending requirements. According to AirDNA, there are three types of STR loans available:

  1. Asset-based loans: Based on income potential rather than the borrower’s income.
  2. Cash-out refinance: Tapping into existing property equity to fund STR purchases.
  3. Home equity lines of credit (HELOCs): Accessing primary residence equity for STR acquisition.

Tenant Turnover: STRs vs. LTRs

Tenant turnover is a pivotal consideration for investors. Long-term rentals generally boast lower turnover rates, thanks to extended leases. However, dealing with problematic long-term tenants can present challenges, from property damage to rent payment issues, especially in states with eviction challenges.

On the flip side, STRs, with their average short stays of 5-7 nights, experience higher turnover. Constant marketing is essential for STR property owners to ensure a consistent income flow. Temporary tenants often use credit cards for stays, covering both accommodation and potential damages.

Navigating Exit Strategies

When it comes to exit strategies, LTR investors may find themselves restricted, especially if they aim to sell with a tenant in place. The challenge of selling a home with a tenant can limit the pool of potential buyers.

In contrast, STR investors enjoy more flexibility in choosing profitable exit strategies. The ability to swiftly respond to changing market conditions without the constraints of long-term leases allows STR property owners to cater to various investor preferences, whether STRs, LTRs, or even owner-occupants seeking a primary residence.

Lifestyle Investing: STRs’ Unique Appeal

For those considering the lifestyle aspect of real estate investing, STRs offer a distinct advantage. Long-term rentals, often situated outside high-demand destination towns and occupied by long-term tenants, don’t provide the opportunity for personal use.

STRs, on the other hand, are strategically located in areas like ski resorts, beach communities, and high-traffic resort towns. This not only ensures a cash-flowing investment but also allows property owners and their families to relish unique experiences.

As advocated in the book “Die With Zero,” which emphasizes creating memorable experiences after securing enough for retirement, STRs align with the philosophy of turning investments into lifelong enjoyment.

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How to Dive into STR Real Estate Investment

If the potential of STRs has captured your attention, here are key steps to consider:

  1. Define Your Goals:
    • Determine if you seek a vacation home with income or aim to build a cash-flowing rental portfolio, whether actively or passively.
  2. Understand Local Regulations:
    • Familiarize yourself with STR regulations in your chosen location, as each market has unique rules governing vacation rentals.
  3. Research STR Markets:
    • Investigate key metrics such as average occupancy rateaverage daily rates (ADRs), operating expenses, seasonal rates, and the major draws to the area.
  4. Run the Numbers:
    • Leverage resources like Airbtics, Vrolio, AirDNA, and Roofstock STR Marketplace to assess crucial metrics like average length of stay (ALOS)cash flow, occupancy rates, cash-on-cash returnADRrevenue per available room (RevPAR)cap rate, and annualized return.
  5. Make an Offer:
    • Similar to LTR properties, crafting a written purchase and sale agreement with specific terms and conditions is crucial. Enlisting an agent to assess the asset and income value can provide insights into the offer’s alignment with market standards.
  6. Closing the Deal:
    • Once an offer is accepted, initiate the due diligence process. After a successful inspection, the lender begins the loan underwriting process. The closing, dictated by state-specific STR laws, is typically managed by a real estate attorney or title company.

As with any investment, the devil lies in the details of STR real estate investing. Both advantages and disadvantages exist, and the choice between STRs and LTRs often boils down to individual goals, risk tolerance, and desired involvement in the investment process.

For those with limited time, like myself and members of our Passive Investors Circle, partnering with reliable entities in the short-term rental space can simplify the investment journey. This strategic collaboration promises:

  • Solid cash flow.
  • Tax benefits.
  • Appreciation.

If you’re keen to explore the deals I personally invest in, consider joining our group today.

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Navigating the Complex Landscape: Key Considerations for STR Investments

Venturing into short-term rentals (STRs) is not merely about securing a property and listing it on platforms like Airbnb or VRBO. Success in this realm requires a comprehensive understanding of various factors that can influence your investment. Here’s a closer look at the critical elements to consider:

Local Regulations and Compliance

Before diving headfirst into the world of STRs, it’s imperative to understand and comply with local regulations. Vacation and short-term rental markets are not uniform in their permissibility, and some areas may have stringent restrictions or outright bans on STRs. Engaging a local real estate agent well-versed in the area’s regulations is not just a good idea; it’s a necessity. They can guide you on registration requirements, permit fees, the need for a business license, and whether there’s a requirement to collect lodging or rental taxes.

Market Research: Identifying Profitable Locations

Not all vacation markets are created equal. Thorough market research is indispensable to pinpoint locations that promise a high return on investment. Investigate metrics such as average occupancy rates, average daily rates (ADRs), operating expenses, and seasonal fluctuations. Understanding the demands of the local market and identifying the key attractions that draw visitors can guide your investment strategy.

Financial Metrics: Running the Numbers

Running the numbers is the bedrock of sound STR investing. Utilize resources like Airbtics, Vrolio, AirDNA, and Roofstock STR Marketplace for real-time data. Key metrics to assess include average length of stay (ALOS), cash flow, occupancy rates, cash-on-cash return, ADR, revenue per available room (RevPAR), cap rate, and annualized return. Factor in maintenance costs and expenses associated with property management if applicable. A thorough financial analysis is vital for making informed investment decisions.

Making Informed Offers: The Art of Negotiation

Crafting a compelling offer is a nuanced art, whether you’re using the services of a real estate agent or navigating the process independently. A written purchase and sale agreement (PSA) should outline crucial terms, including the property address, purchase price, financing details, earnest money amount, and contingencies such as property inspections. Having an experienced agent assess the asset and income value helps ensure that your offer aligns with the prevailing market conditions.

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Closing the Deal: Due Diligence and Transition

Once your offer is accepted, the due diligence process commences with property inspections. Assuming a successful inspection, the lender initiates the loan underwriting process. The closing, in accordance with state-specific STR laws, is typically handled by a real estate attorney or title company. Take possession of the property on the closing day, ensuring that any bookings made before the purchase are seamlessly transitioned to your control. Verify that advance deposits and down payments are accurately reflected in the closing statement.

Unveiling the Potential: STR Investment Strategies

Passive or Active Investment: Defining Your Role

Investing in STRs offers the flexibility to tailor your level of involvement. For those seeking a hands-off approach, passive investment options, such as partnerships with experienced property managers or participation in STR funds, can be attractive. On the other hand, active investors may choose to directly manage their properties, leveraging platforms and tools to streamline operations.

Risk Mitigation: Insurance and Legal Safeguards

Mitigating risks is paramount in real estate investment. STR property owners should secure comprehensive insurance coverage tailored to the unique challenges of short-term rentals. Additionally, understanding local laws and regulations is crucial for compliance. This includes lease agreements, tenant screening processes, and adherence to safety standards. Legal safeguards protect both property owners and guests, fostering a secure and sustainable investment environment.

Crafting Your STR Investment Journey

Embarking on a journey into short-term rentals demands a meticulous approach. By aligning your goals, understanding local dynamics, and conducting thorough research, you position yourself for success in a market that, when navigated wisely, can yield robust returns. Whether you’re eyeing a vacation home with income potential or aspiring to build a dynamic rental portfolio, the key lies in a strategic and well-informed approach.

Stay tuned for the next steps in your STR investment journey, including insights on optimizing property management, marketing strategies, and capitalizing on emerging trends in the dynamic world of short-term rentals.

Nurturing Success: Beyond Acquisition to Optimal Management

Having navigated the initial steps of acquiring a short-term rental (STR) property, your journey now extends to the realm of effective management. This crucial phase involves optimizing your property’s performance, enhancing guest experiences, and ensuring a seamless operational flow. Let’s delve into the key aspects of successful STR management:

Strategic Marketing: Positioning Your Property in a Crowded Landscape

With numerous properties vying for attention, strategic marketing becomes indispensable. Craft an enticing listing that highlights the unique features of your property, emphasizing its appeal to your target audience. Leverage high-quality photos, compelling descriptions, and considerate pricing strategies. Platforms like Airbnb reward well-marketed listings with higher visibility, potentially increasing bookings and maximizing your rental income.

Dynamic Pricing Strategies: Adapting to Market Trends

The short-term rental market is dynamic, influenced by factors such as seasonality, local events, and market demand. Implementing dynamic pricing strategies ensures that your property remains competitive. Platforms like Airbnb offer tools for adjusting pricing based on occupancy rates, demand spikes, and other variables. This adaptability allows you to capture peak seasons, optimize revenue, and respond promptly to market fluctuations.

Effective Property Management: Streamlining Operations

Efficient property management is the linchpin of a successful STR venture. Whether you choose to handle this aspect personally or enlist the services of a property manager, streamlined operations are essential. Attend to maintenance promptly, ensuring the property is in optimal condition for each guest. Respond promptly to inquiries and reviews, fostering positive guest relations. Consider employing smart home technology for keyless entry, climate control, and security, enhancing the overall guest experience.

Guest Experience: Elevating Satisfaction for Repeat Bookings

Creating a memorable guest experience is not just about the property itself but extends to every interaction. Implement thoughtful touches, provide clear communication, and offer local insights to enhance the overall stay. Positive reviews and satisfied guests contribute to higher occupancy rates and increased demand. A focus on guest satisfaction can lead to repeat bookings and positive word-of-mouth, amplifying the property’s desirability.

Capitalizing on Trends: Staying Ahead in the STR Landscape

The short-term rental landscape evolves, influenced by technological advancements, travel trends, and shifts in consumer preferences. Staying abreast of these trends positions you as a proactive and adaptable investor. Explore emerging technologies in property management, consider eco-friendly initiatives, and gauge the impact of remote work on travel patterns. By aligning your property with contemporary trends, you tap into evolving market demands, ensuring the sustained relevance of your investment.

Your STR Success Journey Continues

As you embark on the ongoing management of your short-term rental property, remember that adaptability and responsiveness are key. The STR market rewards those who stay attuned to guest expectations, market dynamics, and emerging trends. In the next segment, we’ll explore avenues for expanding your STR portfolio, optimizing returns, and addressing challenges that may arise in this dynamic and rewarding real estate sector.

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Expanding Your STR Portfolio: Scaling for Success

Having established a solid foundation in the short-term rental (STR) realm, the opportunity for portfolio expansion emerges. Scaling your STR investments involves strategic decision-making, risk assessment, and aligning your portfolio with your overarching financial goals. Let’s delve into the key considerations for expanding your STR portfolio:

Diversification: Balancing Risks and Returns

Diversifying your STR portfolio is akin to constructing a resilient financial ecosystem. Consider investing in properties across different locations, catering to varied demographics and travel preferences. Diversification mitigates risks associated with localized market downturns or unexpected events, providing a buffer against potential challenges. Assess the unique strengths and demand drivers of diverse markets to optimize your portfolio’s stability.

Market Research: Identifying Lucrative Opportunities

Before expanding your portfolio, conduct comprehensive market research to identify promising opportunities. Explore locations with high demand for short-term rentals, assess local regulations, and gauge the competitive landscape. Analyze the performance of existing STRs in the target market, considering factors such as average daily rates (ADRs), occupancy rates, and seasonal trends. Informed decision-making at this stage sets the groundwork for a successful expansion.

Financing Strategies: Navigating the Path to Growth

Expanding your STR portfolio often involves securing additional financing. Assess various financing options, considering factors such as interest rates, loan terms, and eligibility criteria. Explore financing avenues tailored to short-term rental investments, such as asset-based loans or cash-out refinancing. A strategic financing approach enhances your capacity to acquire properties, manage mortgage payments effectively, and optimize returns.

Operational Efficiency: Streamlining Management Across Properties

Managing multiple STR properties demands operational efficiency. Implement standardized processes for property acquisition, onboarding, and maintenance. Leverage property management tools that facilitate centralized control and streamline communication. Whether you choose to handle operations independently or enlist the services of a property management company, efficient processes are integral to sustaining a growing portfolio.

Navigating Challenges: Proactive Problem Resolution

Expanding your STR portfolio may come with unforeseen challenges. Stay proactive in identifying and addressing issues promptly. This could include adapting to changes in local regulations, addressing property-specific challenges, or refining your marketing strategy based on evolving trends. A proactive stance positions you to navigate challenges effectively, safeguarding the performance and value of your expanding portfolio.

Embracing Growth in the STR Landscape

As your short-term rental portfolio expands, embrace the growth journey with a blend of strategic decision-making and continuous learning. In the subsequent segment, we’ll explore advanced strategies for maximizing returns, optimizing property performance, and navigating the intricate landscape of short-term rental investing.

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Advanced Strategies: Maximizing Returns in Your STR Portfolio

Now that you’ve mastered the fundamentals and successfully expanded your short-term rental (STR) portfolio, let’s delve into advanced strategies to optimize returns and navigate the intricacies of the dynamic STR landscape:

Dynamic Pricing Optimization: Maximizing Revenue Potential

Fine-tuning your pricing strategy is paramount in the competitive STR market. Embrace dynamic pricing models that respond to real-time demand, seasonality, and local events. Leverage data analytics tools to analyze market trends, adjust pricing accordingly, and ensure your properties remain competitive while maximizing revenue during peak seasons.

Guest Experience Enhancement: Fostering Positive Reviews and Repeat Business

In the world of short-term rentals, positive guest experiences translate into stellar reviews and repeat business. Prioritize guest satisfaction by providing well-maintained properties, seamless check-in experiences, and responsive communication. A satisfied guest is more likely to leave positive reviews, enhancing your property’s online reputation and attracting a steady stream of bookings.

Technology Integration: Staying Ahead in a Digital Landscape

Stay abreast of technological advancements that can elevate your STR business. Explore property management systems, smart home technologies, and automated communication tools. Implementing technology not only streamlines operations but also enhances the overall guest experience. Automated check-in processes, smart home features, and real-time communication contribute to efficient property management.

Strategic Partnerships: Collaborating for Mutual Success

Consider forming strategic partnerships within the local community or broader industry. Partnering with local businesses for guest discounts or collaborating with complementary service providers can enhance the overall guest experience. Additionally, exploring partnerships with other real estate investors or property managers may open doors to shared resources, valuable insights, and mutually beneficial opportunities.

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Continuous Learning: Adapting to Industry Shifts

The short-term rental landscape is dynamic, influenced by technological advancements, market trends, and regulatory changes. Commit to continuous learning by staying informed about industry shifts, attending relevant conferences, and networking with fellow investors. A proactive approach to ongoing education positions you to adapt to changes swiftly and make informed decisions for the sustained success of your STR portfolio.

Navigating the Future of Your STR Investments

As you embrace advanced strategies and navigate the evolving landscape of short-term rental investing, remember that agility and adaptability are key. The final segment of our exploration will focus on future trends, emerging opportunities, and preparing your STR portfolio for long-term success.

Future Trends and Long-Term Success in Short-Term Rentals

As the short-term rental (STR) market continues to evolve, anticipating future trends is crucial for positioning your portfolio for long-term success. Let’s explore key considerations and emerging opportunities to stay ahead in this dynamic industry:

Technology Evolution: Embracing Innovations for Efficiency

Stay attuned to technological advancements shaping the hospitality and real estate sectors. The integration of artificial intelligence, virtual reality, and enhanced booking platforms may redefine guest experiences and streamline property management. Adopting these innovations can give your properties a competitive edge and improve operational efficiency.

Sustainability and Eco-Friendly Practices: Meeting Guest Preferences

An increasing number of travelers are prioritizing sustainability in their accommodation choices. Consider incorporating eco-friendly practices into your properties, such as energy-efficient appliances, waste reduction initiatives, and sustainable amenities. Not only does this appeal to environmentally conscious guests, but it can also align your business with evolving consumer preferences.

Regulatory Compliance: Navigating Legal Changes Effectively

Keep a vigilant eye on evolving regulations governing short-term rentals. Many jurisdictions are adapting their laws to address the growing popularity of platforms like Airbnb. Stay informed about local ordinances, tax regulations, and licensing requirements. Proactively complying with legal changes ensures the longevity and stability of your STR investments.

Diversification Strategies: Exploring New Markets and Property Types

Diversification remains a potent strategy for mitigating risks and tapping into emerging opportunities. Explore new markets with high demand, considering factors like tourism trends, job growth, and economic indicators. Additionally, assess the potential of different property types, from boutique apartments to unique vacation homes, to diversify your portfolio effectively.

Community Engagement: Building Positive Relationships Locally

Foster positive relationships within the communities where your STR properties are located. Engage in open communication with neighbors, address concerns proactively, and contribute positively to the local economy. Building a good rapport within the community not only enhances the reputation of your properties but also positions your investments favorably in the eyes of local authorities.

Adapting Marketing Strategies: Staying Visible in a Crowded Market

As the STR market becomes increasingly competitive, refining your marketing strategies is essential. Leverage social media, search engine optimization (SEO), and online travel agencies to maximize visibility. Highlight unique selling points, such as exceptional amenities, tailored experiences, or proximity to popular attractions, to attract your target audience effectively.

Your Journey to STR Success

Armed with a comprehensive understanding of short-term rental dynamics, advanced strategies, and future considerations, you are well-equipped to navigate the diverse landscape of real estate investing. Whether you’re a seasoned investor or exploring STRs for the first time, continuous learning and strategic decision-making will be your allies on the path to success.

For personalized insights, tailored recommendations, or to explore exclusive investment opportunities, feel free to reach out to Jeff Davis at jeff.davis@bridgestoneinvest.com. Additionally, subscribe to the Supply Chain Investor Newsletter for the latest updates and valuable insights at Bridgestone Invest.

Your journey in short-term rental investing awaits – embrace the opportunities, stay informed, and thrive in this exciting and dynamic real estate sector.

Navigating Challenges and Mitigating Risks

Investing in short-term rentals (STRs) can be a lucrative venture, but it comes with its own set of challenges and risks. Understanding these factors is crucial for any investor looking to capitalize on the booming short-term rental market. Here’s a closer look at how to navigate challenges and mitigate risks:

  1. Regulatory Compliance: Before delving into the world of short-term rental properties, it’s essential to grasp the local laws and regulations governing these investments. Local governments often have specific rules regarding the use of properties for short-term rentals. Consulting with a knowledgeable real estate agent or legal professional can provide insights into zoning laws, permit requirements, and any restrictions imposed on vacation rentals.
  2. Market Research: Conduct thorough market research to identify the best locations for your short-term rental investment. Analyze key metrics such as average daily rate (ADR)occupancy rates, and seasonal demand. Platforms like Airbnb and VRBO can offer valuable data on the performance of similar properties in your target area. Understanding the short-term rental industry in a specific location is crucial for making informed investment decisions.
  3. Property Management: Managing a short-term rental property requires a proactive approach to ensure a seamless experience for guests. Consider partnering with a reputable property management company specializing in STR properties. They can handle tasks such as guest communication, cleaning, and maintenance, allowing you to focus on the strategic aspects of your investment. This is especially beneficial for real estate investors who prefer a more hands-off approach.
  4. Risk Mitigation Strategies: The short-term rental market is susceptible to factors like seasonality, economic downturns, and unexpected events. Diversify your portfolio across different locations to minimize the impact of regional economic fluctuations. Additionally, implementing flexible pricing strategies based on demand can help optimize rental income during peak seasons.
  5. Financial Planning: Understand the financial implications of investing in STRs compared to long-term rentals (LTRs). While the potential for higher cash flow exists in short-term rentals, the income can be more variable. Plan for potential vacancies during off-peak periods and allocate funds for property management, marketing, and regular maintenance. Thorough due diligence in financial planning is key to long-term success.
  6. Exit Strategies: Unlike long-term rental investmentsshort-term rental investors have the flexibility to choose from various exit strategies. Whether selling to other investors, transitioning to long-term rentals, or selling to owner-occupants, having multiple options enhances your adaptability to changing market conditions. This agility is a notable advantage in the ever-evolving real estate landscape.

Your Strategic Partner in Short-Term Rental Success

Embarking on a short-term rental investment journey can be both exciting and rewarding. However, having a strategic partner can significantly enhance your chances of success. If you’re a busy professional with limited time, consider partnering with experienced professionals in the short-term rental space.

You should seek a local real estate agent or an active partner in the market/space you are interested in.

  • Solid Cash Flow: Maximize your rental income with our proven strategies for pricing optimization and occupancy management.
  • Tax Benefits: Explore potential tax advantages associated with short-term rentals and make informed decisions to optimize your financial outcomes.
  • Appreciation: Benefit from our insights into market trends and capitalize on opportunities for property appreciation in high-demand areas.
  • Streamlined Processes: We handle the complexities of property management, allowing you to enjoy a truly passive investment experience.

If you’re eager to learn more about the deals we invest in and how you can achieve financial success through short-term rentals, join our exclusive group today. Subscribe to the Supply Chain Investor Newsletter and stay informed about the latest trends and opportunities in the real estate market.

Invest wisely, invest strategically, and unlock the full potential of short-term rental real estate. Contact us today at jeff.davis@bridgestoneinvest.com or subscribe to the Supply Chain Investor Newsletter here.

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To receive information about passive income ideas please contact me at jeff.davis@bridgestoneinvest.com. We have syndications going on throughout the year.

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