Mastering Guest Communication: Why It Matters and How Wilkuma Can Help
Mastering Guest Communication: Why It Matters and How Wilkuma Can Help
A Successful short-term rental property isn’t just about having a beautiful space in a great location; it’s also about delivering a five-star guest experience. One of the most overlooked but essential pieces of that puzzle is guest communication. Wilkuma is your local Massachusetts vacation rental manager; we are experts at guest communications as it relates to your vacation rental property.
Whether your vacation rental is in Gloucester, Rockport, Manchester-by-the-Sea, or anywhere on the Cape or Berkshires, Massachusetts vacation rental management services like Wilkuma exist to take that burden off your plate, so you can stop stressing and start seeing better reviews, higher ADR/Occupancy Rates, and higher gross annual booking revenue.
If you're managing your vacation rental independently, here's a comprehensive look at what effective guest communication entails.
Gloucester Vacation Rental Houses, Managed by Wilkuma
Pre-Booking Communication Checklist
This is your chance to make a great first impression and win the booking.
Respond to all inquiries within 1 hour (ideally less)
Provide clear, concise property information (this should be a saved canned message that goes out every time)
Answer all questions thoroughly and quickly
Be transparent about house rules and policies and allow the guest to confirm they understand the rules
Responsiveness and professionalism matter. Delaying a reply or sending vague information risks losing the booking altogether, and your ranking on Airbnb and VRBO will be impacted by slow response times. Wilkuma properties all receive sub 1 hour guest responses.
Post-Booking / Pre-Arrival Checklist
Once the booking is confirmed, it’s time to shift to prep mode.
Send a booking confirmation email within 24 hours of the booking (generally Airbnb & VRBO will do this for you, but for direct bookings, you will need to send this).
Provide a welcome guide with:
Check-in instructions
Wi-Fi password and network name
House rules reminder
Local attractions and recommendations - we like to provide a list of nearby restaurants that we recommend, and any shops or attractions that might be off the radar, and will give guests a more local experience.
Pre-arrival message 2–3 days before check-in:
Confirm arrival time
Provide contact info for emergencies
Offer directions and parking info
Sending messages in this sequence will help set expectations and reduce guest anxiety. First impressions matter, and getting off on the right foot with your guests is important to guest experience.
Guest Check-in Day Checklist
When guests arrive, they should feel welcomed and supported.
Send a check-in reminder with key/lockbox info
Be available by phone or message for any issues (this is super important)
Send a welcome message after check-in
Confirm everything is satisfactory after they check in to get ahead of any issues they may have and remind them you are 100% available if they need.
Check-in is often when issues surface—lockbox confusion, driveway mix-ups, Wi-Fi questions. Being proactive keeps everything running smoothly.
During the Stay Checklist
Your role isn’t done once they’re in the door.
Check in midway through longer stays
Respond promptly to any messages or concerns
Communicate clearly about resolution steps if issues arise
Problems happen. It’s how you handle them that guests remember—and review.
Check-Out Checklist
Make departure just as easy as arrival.
Send a reminder the day before check-out
Confirm check-out time
Provide any special instructions
Send a farewell message on check-out day
Thank guests for staying
Provide key return/lockbox instructions
Remind about leaving a review (this is essential and needs to be done in a way that converts reviews)
A thoughtful goodbye closes the loop and encourages that glowing review.
Post-Stay Checklist
Don’t skip this step—this is how you build long-term loyalty.
Send a thank-you message within 24 hours
Direct mail marketing to the guest so if they want to book again next year they are able to book direct and save Airbnb & VRBO fees
This is your last touchpoint. Done right, it leaves a lasting impression—and encourages repeat bookings.
General Communication Tips
Whether you’re messaging once a day or 20 times a week, these habits keep things professional.
Always maintain a friendly, professional tone
Use templates for consistency, but personalize when possible
Proofread all messages before sending
Keep response times under 24 hours (preferably much faster)
Use a guest communication platform to stay organized
Feeling Overwhelmed with Guest Communications? That’s Where Wilkuma Comes In.
At Wilkuma, we handle everything you just read—automated, personalized, professional guest communication from pre-booking to post-stay. Our team is local, responsive, and trained to handle every message with care. We use smart tools and real human support to make sure your guests feel seen, heard, and taken care of—so you can enjoy passive income without the late-night texts.
Our Massachusetts vacation rental management services are set up to make your life easier and your property more profitable.
Let’s chat: hello@wilkuma.com
Or call us at 781.691.0029
