Managing Your Vacation Rental

Who Is Today’s Vacationer?

Written by Elizabeth Weedon
5/5 - (2 votes)

Updated December 2023

The importance of knowing your customers

Why is it important to know what vacationers want? Because an owner’s attention to the guest experience at their home is vital to the success of managing a short-term rental (STR) these days.

No longer is it adequate to simply provide a roof over someone’s head. Stiff competition and increasingly more demanding vacationers require hosts to up their game and to do whatever they can to assure the happiness of their guests.

Meeting the needs and wants of guests results in great guest reviews, more repeat guests, and the ability to get top dollar for your home. It also avoids contention, negative reviews, and even complaints.

Times change, and so do vacationers

For many, many years, vacationers have demanded, at the very least, two criteria for a short-term rental: that the home be clean and in good working order.

But more recently, and particularly since the start of the pandemic, general attitudes and expectations have evolved. Propelled by fears of Covid, vacationers have a heightened sensitivity to cleanliness. They are also paying considerably more for rentals than they did even a few years ago, and their expectations of the vacation home have risen significantly as a result.

What we learned from our Vacationer Survey

Curious to know the make-up of the current vacationer market, we asked over 2,000 survey takers about their vacationing habits.

Nearly 70% of respondents visit the Cape or Islands at least once a year. It’s a way of life, part of the fabric of their lives, a tradition that they likely started when they were children.

In addition, the pandemic converted many vacationers who had previously stayed only in hotels or inns. In fact, 12% of those surveyed had never rented a STR anywhere prior to the pandemic. So, they were new to the industry and were used to a hotel or resort-type experience (cleanliness, lack of clutter, guide to the area, almost concierge-type service, etc.).

Facilitating the booking process

In the survey, vacationers made it very clear that it was important for them to be able to communicate directly with the owner prior to booking. By phone, email, text, they feel safer and more comfortable having direct access to you.

But they don’t want to waste a lot of time and energy with the booking process. They expect:

  • Up-to-date calendars
  • Transparent pricing (no hidden fees!)
  • The ability to pay electronically

Enter your pricing and availability for next year in the fall

Despite the trend towards a significant increase in early bookings for the following seasons, tell us in the fall that they are not ready to enter pricing and availability for the following summer. Not only are these owners missing out on valuable early bookings, but vacationers may leave our site in frustration due to the lack of available homes to choose from.

Responding to inquiries promptly

Response time can impact your bookings. Vacationers could be looking at multiple homes, eager to reserve/confirm, or just kicking tires (which is when you have their attention). Without timely responses comes frustration and lack of trust.

This was born out in our vacationer survey in which virtually all respondents indicated that prompt responses to their inquiries are either Very Important (86%) or Somewhat Important (13%).

Many owners complain that they do respond to inquiries, and then they hear nothing back from the vacationer. Unfortunately, that happens. But your best option is to respond promptly and look to see if they provided a phone number to call/text.

The dilemma of how to handle repeat guests

A number of owners hesitate to open their calendars because they are waiting for commitments from past guests. But how long should you give them to book? While you certainly don’t want to lose a repeat guest, you may miss out on new ones by waiting until December or January.

So, you have to consider this: How much is a repeat guest worth to you? You don’t have to treat all guests the same – someone who has stayed with you for 2+ years is more likely to return than someone who only came this past summer.

The earlier demand we’ve been seeing is reason to request a small deposit sooner than you used to.

The importance of good communication

When asked to rate the host services they appreciate in a rental, vacationers responded that contact from the homeowner prior to arrival (72%), receiving a Welcome Book/Info (71%), general communications (86%), and clear check-out instructions (92%) were all very important to them.

Vacationers want you to be accessible to them, they want to know where things are and how they work in your home, and they want you to be clear about what’s expected of them.

What part of a listing most impacts their choice of rentals?

Vacationers were asked to rank aspects of a listing by how they impact their decision to inquire about a rental.

  • The first item, Good & accurate pictures, was rated the MOST important (91%). Only 8% said Somewhat Important, and less than 1% said Not important.
  • Good pictures and informative Property Descriptions both had highly weighted responses.
  • While only 45% said having plenty of guest reviews was Very Important, as many as 52% said Somewhat Important, and only 3% said Not Important.
  • Ability to pay online: 39% Very Important, 41% Somewhat Important, and only 21% Not Important.

Vacationers demand transparent pricing

A common question from vacationers when inquiring about a home is, “What is the full cost including fees?”

No one likes to feel like they’re getting taken advantage of. Costs, even if optional or refundable, should be stated up front on your listing.

And of course, if there are lengthy check-out requirements on top of extra fees, it can be very annoying to your guests.


Take trash to the dump?! Not exactly the vacation experience one would hope for. (Another rental outside the Cape made headlines by requiring the lawn to be mowed by the guest!)

Ability to pay electronically

The vast majority of vacationers surveyed said that the ability to pay an owner electronically is either very or somewhat important to them.


Online payments for booking can be extremely efficient and convenient for both vacationers and owners. Within a few minutes, guests secure their rental, and homeowners gain bookings without having to wait for a check – and possibly lose other guests in the meantime.

And most of your competition does allow for online payments:


The most popular amenities and how many homes offer them

Below are the top 12 most popular amenities found in Searches on our site, and in the column on the right are listed the percentages of homes on our site that offer each amenity.


As you can see, pet-friendly homes are in demand, but only 24% of rentals allow them. Also, the vast majority of owners provide AC, washer/dryer, Wifi, an outdoor shower, a deck/porch/patio, cable TV/streaming, and a dishwasher – so if you don’t, you are clearly in the minority

In our Vacationer Survey, over 60% of vacationers indicated they would not rent without some kind of AC, 34% said they would like it, and only 5% said they don’t need it.

The value of first impressions

After cleanliness, a lack of basic supplies and kitchen essentials are among the most bothersome to vacationers. Although they don’t make or break a guest’s stay, it can be frustrating to guests to have to either purchase some items or do without them.

We saw a guest review giving a listing 3 stars, saying, “It would have been 5 but for the lack of supplies.”

As for a well-stocked kitchen, people cook in your home more than you might think, and attention to detail will go a long way with them. They don’t appreciate poor quality knives, for example, or hand-me-down utensils and mismatched plates and glasses.

Tips to improve your guests’ experience

Perhaps you can identify adjustments you can make to your management practices such as:

  • Live in your rental, experience it as a renter would or solicit honest feedback from a family/friend who stays. Do all the lightbulbs work? Are the overhead light globes clean? If the power went out, would you know where to find a flashlight? Are the knives sharp? Are there ample hangers?
  • Identify the little things, attention to detail, that will show guests you care for your home and their stay.
  • Review your communication plans – too much, too little, available in advance. And find ways to make it easier for yourself, using templates and a good booking management system.

[The homeowner] was an outstanding person, so helpful, warm, sincere, and such a pleasure to rent from. Her home was so lovely, cozy and the amenities were perfect in every way.

Summary of the keys to successful rental management

Being aware of what vacationers care about these days is the important start, enabling you to market your home to those tastes and attract as many vacationers as possible. Offer a thorough and up-to-date listing, including transparency in your pricing and what’s included, and then, create a smooth and efficient booking process for them. And finally, provide a well-maintained and provisioned home, great communications, and thoughtful attention to detail to award your guests a top-notch experience while they’re in your home.

About the author

Elizabeth Weedon

Elizabeth Weedon - Although I’ve worked for since 2008, I’ve been a loyal homeowner on the site since early 1998, just a few months after the website was launched by the Talmadges. I grew up summering on the Vineyard and managed my family's rental home there since the mid-1980’s. I’m passionately devoted to the Vineyard – and to WeNeedaVacation, which I credit with enabling me to hold onto the special property that has been in our family for nearly a century. An enthusiastic member of the WNAV Homeowner Support Team, I endeavor to keep my finger on the pulse of the Cape and Islands vacation rental industry so that I can provide homeowners advice about how to ensure their booking success with us. With owner Joan Talmadge, I am also responsible for editing and writing much of the text on our website, our monthly newsletters, and Homeowner Blog posts.


  • Very well done, Elizabeth. Fortunately for us there up in Chilmark, we’ve only had one query about air conditioning. So that’s one thing we haven’t provided…yet. Also, none of our renters complain (yet) about our not having electronic means of payment.

    Thanks so much for all you do to help us provide a “quality product.” You ARE appreciated!

    John and Caroline Moore

    • Thank you, John, for your thoughtful comment! It means a lot, I assure you. As for “holding out” on getting AC, good for you! Just keep in mind that, even though vacationers might not ask you about it, they do have the ability to search by that amenity. So your listing simply doesn’t even appear to them. If you are getting plenty of inquiries and bookings, it’s a moot point. But if you’re not, it’s possible the lack of AC is making an impact.

  • Multi week, multi year tenants is our priority.
    Respect for our property, consistent patronage, is why new prospective tenants must be relegated to fill in open weeks.
    Paul FLAHERTY #6620 #5997