7 Common Challenges For Startups In The Vacation Rental Market

  • Challenges for startups can come in a variety of packages. These can range from technical challenges with your website to having the right partners helping run your business run smoothly.
  • Startups will also have to deal with customer expectations and clearing laying those out to ensure they have the best possible experience. And staying current on all legal matters is crucial to not only keeping your business afloat but also avoiding any costly fines or lawsuits.
  • Another challenge is hiring the right people, which will determine how efficiently your business runs. Within that same principle is having the financial discipline to ensure the business is run responsibly and has the necessary resources to continue operating. Finally, winning customers' trust is one of the toughest challenges for any startup to face, but once it has been done, a business is on a straight path toward success.

1. Staying on top of website issues

In this industry, your website is the backbone of the business. Even when you’ve perfected your code, issues will still pop up here and there. An image may not be showing up; an integration isn't working as well as expected; a payment gateway may not work properly, and transactions can’t go through.

You need to be responsive and fix the issues as soon as possible. Prioritise your tasks and determine which issue should be tackled first. A common mistake people make is fixing the issues as soon as they arise, yet some are more urgent while others can wait.

2. Finding the right partners

It’s crucial to find the right partners to work with. As an online company, you will have to rely heavily on third parties, and your reputation depends on them. Your business will suffer whenever your customers have a terrible experience with a third party. Therefore, make sure that you only work with professionals you can trust.

Meet them, talk to them and test their services to understand the quality of services you are offering to your customers. As your company grows, you will receive more offers to collaborate, but not every single one will fit your goal. Be selective and resist the temptation to partner with everyone who comes to you. Remember that quality is more important than quantity.

3. Managing customers’ expectations

Problems arise when there is a mismatch in customers’ expectations and your deliverables. Take great care to avoid any miscommunication, overpromising and under-delivering. Be honest about what you can and cannot do and communicate that clearly. As William Howard Taft said, “Don't write so that you can be understood, write so that you can't be misunderstood.”

While you may promise the best experience for your customers, sometimes things may be out of your control. You need to have clear judgment to determine where your responsibility lies and when an issue is not yours to own.

4. Getting the legal matters right

It’s never fun to run into legal problems. If you are in the emerging vacation rental market, regulations may change quickly. You might also operate in several countries while dealing with many hosts. From a legal perspective, how do you enter a new market? What if something happens during a customer’s stay? Make sure that you understand the legislations, pay your tax, get your business visa and have everything clear in the terms and conditions to avoid getting into trouble.

5. Hiring the right people

Hiring the right people

As you grow, you will need more people in the company, and that can be a real challenge. You want to find people with the right skills, attitude and fit in well with the organisation. Having a talented team and keeping them happy are extremely important as they represent your brand, your values and help ensure that customers have a wonderful experience.

On the other hand, having a misfit in a small team can create a big issue. Aside from the problem itself, the team’s morale is also affected. As an entrepreneur, you have enough to deal with, and the last thing you want are internal issues. Set up your hiring process, be selective and only hire those who align with your company’s values.

6. Having financial discipline

Keeping good finance is one of the most common challenges for any startup. You need to have enough capital to sustain the company. It’s vital to have your budget well planned and spend on the right things. Know where your money is coming from, where it goes, and what your return on investment is. Having good financial discipline will allow you to focus on improving the business.

7. Winning customers’ trust

Winning customers trust

It’s hard to win your customers’ trust when they can’t see you in person. You will have to convince them to part with their money to try your services through your website. Therefore, your site must look credible with testimonials from those who have tried your services.

Having a solid “About Page” where you introduce the business, the team, your missions and visions will help the customers understand the company better. But above all, make sure that you keep your promises and deliver results. No amount of words or marketing magic can cover up a poor experience.


David Chambat

CEO at Villa-Finder.com

David Chambat is the Founder and CEO of Villa Finder, an innovative platform for consumers to find and book a villa in Asia. Villa Finder, a Singapore-based company, owns and operates Villa-Bali.com – featuring more than 500 private villas in Bali and Villa-Phuket.com, Samui-Villa.com, Mauritius-villa.com and SriLanka-Villa.com. The company leads the villa distribution in Asia-Pacific with more than 1,000 villas for rent.


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Deborah Vella

Deborah Vella , Owner at Support Legal

Thanks for sharing David. I second point number 4 to get the legals right. It is well worth the effort to make sure you are well organised to prevent unnecessary problems in the future.

Jef Lippiatt

Jef Lippiatt , Owner at Startup Chucktown

I think managing expectations and hiring the right people go hand in hand. If you hire the wrong people it is hard to meet and exceed customer expectations. Also, focusing on being great at a few things rather than trying to be everything to everyone will put you ahead of most of your comopetition. It sounds counter-intuitive but it is true.

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