Creating a vacation rental space that guests love so much that they can’t wait to return isn’t just about the location, especially if you’re in a sought-after area like Oahu or Maui.

What truly makes your property stand out are the features and thoughtful touches you offer that turn a great stay into an unforgettable one!

Whether you’re a seasoned vacation rental owner or just starting, here we have listed a few simple steps on how to get repeat guests to your vacation rental every time they visit your area.

Why Are Encouraging Repeat Guests Important to Vacation Rentals?

Having repeat customers is a total game-changer for your vacation rental business. Not only do they bring good vibes and trust, but they’re also way cheaper to keep around than finding new guests.

Everyone knows it costs a lot less to keep your existing customers happy than to always chase after new ones. So, while we suggest you not stop promoting to new customers, you should definitely invest some cash in keeping your repeat renters coming back.

They already know your rules and pricing, so you don’t have to explain everything a million times. This makes everything run smoother and cuts down on any drama.

10 Steps to Getting More Repeat Guests

We have researched thoroughly and figured out ten steps to making your vacation homes profitable by attracting more loyal guests.

More Repeat Guests

Step 1: Understand Your Guests Needs

Before you start figuring out how to get repeat bookings to your rental properties, you gotta know why they picked your place and your area in the first place. What’s the draw for them?

It may be because you are offering a calm workstation space or a fully loaded room perfect for a family vacation. Or maybe your property is safe for women visitors. It could be anything, but you’ve got to notice and make a note of it.

Some amenities you can add to attract guests are, if you’re getting returning guests coming to work remotely, give them easy access to a WiFi connection. For example, I love spending time by the pool and working. So, I am looking for a place with a good pool, a good internet connection in that area, and comfortable seating.

I also look for the drink options they serve, be it cocktails, mocktails, or shakes that I can have while I’m working. By nailing the experience right off the bat, you’ll have satisfied guests who will keep coming back.

Giving Them a Nice Welcome

Step 2: Focus on Giving Them a Nice Welcome

Whether it is a high-end hotel or a short-term rental business, customer loyalty is what will help you get repeat business. Therefore, you’ll put every effort to make sure you increase customer loyalty and repeat booking.

The first way to do this is to welcome them warmly. You can offer welcome drinks or a welcome basket filled with snacks or gifts.

To add a personal touch, add a nice and sweet welcome note to make the guests feel valued. You can add the basic house rules of the vacation rental, your contact number, and local suggestions about where they can get around during the stay.

Adding this information to the note is a way of relationship building that will definitely benefit you in the long run, fostering guest retention.

Quality Check Your Space

Step 3: Quality Check Your Space

First impressions last, so take a thorough look around your rental. Examine whether the furniture and appliances are modern, up-to-date, and in good working order. Are they aesthetically pleasing as well as functional?

Assess the decor to ensure it creates a welcoming and comfortable atmosphere that invites relaxation and comfort.

It’s essential to remember that your space doesn’t just need to serve functional purposes; it should also evoke a sense of warmth and comfort. If it feels like a home away from home, your odds of having repeat guests increase!

Assess Your Amenities

Step 4: Assess Your Amenities

Guests often choose vacation rentals over hotels for the extra amenities that can make their stay more comfortable and personalized.

To cater to guests who enjoy cooking, it’s important to ensure your kitchen is fully equipped with all necessary appliances, utensils, and cookware. For business travelers or those who blend work with leisure, high-speed internet, and a dedicated workspace are vital for productivity and staying connected.

Don’t forget the importance of entertainment options to enhance the guest experience; offering streaming services for a wide range of movies and shows, along with a selection of board games, can provide special nights filled with fun for your guests.

Focus on Comfort

Step 5: Focus on Comfort

A good night’s sleep can make all the difference! Investing in high-quality mattresses and soft, luxurious linens can significantly enhance their sleeping experience, ensuring they wake up feeling refreshed and rejuvenated. Trust us, nothing turns off repeat guests like an awful night of sleep.

Consider the overall comfort of your rental, which plays a vital role in their satisfaction. Pay close attention to the climate control system; can your guests easily adjust the temperature to suit their personal needs? These occasionally overlooked necessities can make all the difference in the quality of their stay.

Thoughtful Vacation Rental Touches

Step 6: Add Thoughtful Touches

Small details frequently create the most memorable experiences! Providing a welcome basket filled with local delicacies, a guidebook featuring your favorite dining spots and activity recommendations, or even basic beach gear — such as towels and chairs — can dramatically elevate the overall guest experience.

Consider travel-sized shampoo and conditioner bottles, hair dryers, and other specialty items. These thoughtful touches not only enhance their stay but also demonstrate a genuine care for their well-being and enjoyment, going beyond merely offering a place to sleep.

It’s these nuanced gestures that resonate deeply with guests, making their visit unique and showing them that their comfort and satisfaction are your top priorities. They’ll know next time when they are one of your repeat guests that you really do go above and beyond.

Market Your Property Right

Step 7: Market Your Property Right

To attract more guests and stand out in a crowded market in the vacation rental industry, updating your online listings with high-quality photos showcasing your rental in the best light is paramount. Provide detailed descriptions that accurately capture what guests can expect during their stay.

Don’t just list the amenities; describe them in a way that paints a vivid picture for potential guests. Highlight the unique features and selling points of your rental that set it apart from others in the area, such as a scenic view, proximity to local attractions, or any special services you offer.

Additionally, don’t forget to encourage repeat guests through outlets like email marketing newsletters and social media!

Listen to Guest Feedback

Step 8: Listen to Your Guests

Feedback is invaluable. Regularly scrutinizing guest comments can provide you with priceless insights into the aspects of your vacation rental that excel and identify areas ripe for improvement.

Even negative guest reviews should be seen as golden opportunities to pinpoint and rectify issues, demonstrating to future guests your unwavering commitment to offering an exceptional stay.

Taking the time to respond thoughtfully to feedback not only shows your dedication to guest satisfaction but also helps you continuously elevate the quality of the experience you provide.

Not to mention, future guests will be able to see that you promptly responded and are working to correct any issues another guest may have encountered.

Partner with the Pros

Step 9: Partner with the Pros

Partnering with a reputable local vacation rental management company can significantly elevate your rental property from good to great! These companies offer comprehensive services that cover all aspects of property management.

They should adeptly handle guest queries and swiftly resolve any issues or concerns to ensure a smooth and enjoyable stay for each visitor.

If any maintenance matters arise during a guest’s stay, they’ll promptly address the repairs and will work with you to ensure your property stays in pristine condition.

Beyond just upkeep, they go the extra mile to ensure the property is spotless and welcoming for each new arrival, embodying the 5-star service guests expect and deserve.

This not only enhances the guest experience but also boosts the property’s reputation, potentially leading to higher occupancy rates and more positive reviews.


Step 10: Offer Them Exciting Deals on their Next Stay

Trust me, guests love freebies, discounts, and exciting deals! So, why not provide guests with the same?

If you can identify potential customers who can become loyal customers, you can offer them exceptional service and unmatched deals that will keep them coming back to your property.

You can offer them discounted rates on their next trip or a day of a fully sponsored tour around the place. Think of something that your competitors are not doing that makes you different from them.

You can also suggest a referral program and encourage repeat guests to bring their friends and family with them. While your guests can get points that they can use while booking rooms with you, the people they’ve referred can get free nights on their first booking or an impressive discount on multiple bookings.


How can I personalize the guest experience to encourage repeat bookings?

Personalization can include greeting guests by name, leaving a welcome note, offering local recommendations tailored to their interests, and remembering their preferences for future stays.

How can I maintain communication with past guests without being intrusive?

Send periodic emails with updates about your property, special offers, or local events. Ensure the communication is friendly, relevant, and not too frequent to avoid being perceived as spammy.

What are some common mistakes to avoid when trying to attract repeat guests?

Common mistakes include neglecting communication, failing to address guest feedback, letting maintenance issues slide, offering inconsistent service, and not personalizing the customer experience. Consistency and attention to detail are key.

Ready to Learn More About Partnering with a Local Manager?

With the right management partner, you can turn your Oahu or Maui vacation rental property into a successful and profitable investment!

So don’t wait any longer; take the leap and start making the most of your valuable asset today. We can start working together to ensure your guests have an amazing experience and turn into repeat guests who keep coming back for more.

You can learn about our services by clicking below, and please feel free to reach out to us if we can help you in any way:

Maybe you’re looking to purchase your first vacation rental in Hawaii or add to your portfolio. We have you covered! Head over to our real estate website to search properties by clicking here.