How to Capture More Last-Minute Bookings and Win All 5 Stars Doing It

Capture direct bookings

By The Hospitable Team

While last-minute bookings can do wonders for your occupancy rates, they can also create operational nightmares. Success means not just winning those last-minute reservations, but also providing the same quality guest experience as you’d deliver if your guest had booked months in advance.

We sat down with expert Alex Alioto, Head of Growth at Whimstay, which specializes in helping hosts capture last-minute bookings. We picked his brain to share some of his advice on how you can earn more last-minute reservations and deliver the vacation experience your guests deserve.

Specifically, we cover:

  • Why you should care about last-minute bookings
  • What makes last-minute guests special
  • Strategies to capture more last-minute reservations 
  • How to deliver a fantastic guests experience at no notice automates nearly 100% of your guest messaging.

And now, we’re building an end-to-end direct booking solution so you can extend your exceptional hospitality to direct guests.
Start today with a 14-day free trial.

Last-minute bookings are increasingly commonplace

“After Covid, there was a massive bump in travelers going to vacation rentals, and that bump has maintained,” Alex explains.

“People started to discover vacation rentals for a number of different reasons. They could travel but  didn’t necessarily want to get on a plane, and so they wanted to drive instead. They didn’t necessarily want to go to a hotel because they didn’t want to go through lobbies and have to wear a mask at the pool.”

And the statistics back up what Alex says:

  • HomeToGo and Transparent found that 90% of surveyed property managers in the US saw an increase in last-minute bookings in 2021 compared with previous years.
  • Meanwhile, this AirDNA trend report found that 59% of families were more likely to drive instead of fly on their next trip.
  • And Evolve reported that 86% of surveyed travelers planned to book a vacation rental some time in 2022.

So there’s every indication that the last-minute vacation rental market is going from strength to strength—which is why you should have a strategy in place to win and accommodate last-minute guests.

What to know about last-minute guests

The first step to capturing last-minute bookings and delivering an amazing guest experience is understanding what differentiates last-minute bookers from other guests.

Studies show that a growing proportion of last-minute bookings are made on a mobile device.

“We’re seeing that there are all these different types of travelers now that weren’t booking vacation rentals before. And a whole new generation, the millennial and the Gen-Z travelers that make up about 151,000,000 travelers in the United States, spent about $400 billion in travel last year. They’re choosing vacation rentals over hotels” says Alex.

But, according to Alex, it’s not just Gen-Z travelers who are choosing to stay at the last minute: “We’re seeing a lot of retirees, we’re seeing a lot of digital nomads,” he explains.

Keep in mind these key characteristics of last-minute bookers:

Last-minute bookers are looking for a deal

Many travelers opt to book at the last minute because of the discounts. If you find you have rooms available a week ahead of time, consider running a campaign to keep your prices competitive.

“You’re going to need a good discount. This is expired inventory. This is inventory that otherwise is not going to sell” Alex observes.

But of course, you need to achieve a balance between being competitive, attracting guests, and meeting your business needs. 

So, as Alex says, “The first thing is to understand the importance of a discount that makes senseone that makes sense in your bank account, and is aggressive enough to not only drive people to the property but also get them to actually book it.”

Your last-minute guests are more likely to book using mobile

Take into account that the majority of those bookings will come from mobile users. 

In order to improve their overall booking experience—and to prevent them from jumping ship before making their reservation—be sure to optimize your website for mobile and perfect the user experience (UX). Here are three key ways to achieve that goal:

  • Make your website design intuitive to use.
  • Get rid of any excessive text or visual distractions.
  • Minimize the number of steps it takes for website visitors to make a booking. 

Pro tip. You can easily create an intuitive booking experience on your existing website and sync your calendars with OTAs by embedding’s booking widget.

Last-minute guests more likely to be tech-savvy

Make sure guests can easily access fast and reliable WiFi during their stay. To make the connection as fast as possible, separate your personal network from the one that your guests use. If your stay welcomes pet owners and families with children, make sure the router is out of reach. That way,  guests will be less likely to move the device and change its settings.

They might be short on time

Last-minute bookers are less likely to have planned much before traveling. So, make it clear in your listing and guestbook that you can give guests local advice on restaurants, attractions, and upcoming events. 

They could be arriving tomorrow morning

You need to have solid processes in place for your turnovers and guest communications to handle last-minute changes. To stay one step ahead, schedule cleanings as soon as guests check out. That way, you can have your rentals clean and ready to go at a moment’s notice.  

Capture more last-minute guests with these strategies

Now that we’ve looked at some of the characteristics of last-minute guests, here are some solutions that will help you capture more last-minute stays.

Be extremely responsive to inquiries

“When guests are booking last minute, they don’t have time to wait on slow replies—miss a notification, and you lose the business. So responsivity is absolutely key,” says Alex.

To make sure your guest communication is always on point, use a STR message flow. With, this is all automated so you have no extra workload.

All the information is sent out in bite-sized chunks over the course of the guest journey, from pre-stay to post-stay, including:

  • Your guest’s booking confirmation
  • Arrival, access, and stay essentials, like the WiFi password
  • A check-up message to make sure there are no issues
  • A check-out message on what to do or turn off before leaving
  • A review request 

And when your last-minute booking doesn’t leave enough time for a normal message flow, Hospitable recognizes this and adapts the message flow accordingly so your guest still receives all the key information when they need it. 

You can see how this works in our tutorial on check-in instructions for last-minute reservations. automates nearly 100% of your guest messaging.

And now, we’re building an end-to-end direct booking solution so you can extend your exceptional hospitality to direct guests.
Start today with a 14-day free trial.

Offer competitive pricing and incentives

As we know, last-minute guests are looking for a discount. By creating special deals and offers, you’re selling stays that would otherwise slip into the ether.

With Hospitable’s pricing feature, you can save time by making multiple pricing updates from one convenient location. 

This also allows you to integrate smart pricing tools used to make updates based on the market’s condition. If you’re trying to stay competitive, this is the best way to be responsive to market trends and develop the most enticing and profitable pricing strategy for your properties.  

Reduce your minimum number of nights per stay

Before the pandemic, travel usually meant taking a week or more off work.

But, as Alex points out, the rise in remote work has been a real game-changer for the vacation rental industry. “Now it’s kind of these multiple micro-vacations every year. You can take five, six, or even seven of these three-to-four-day vacations—because you can work remotely.”

When thinking about your listing, make sure you don’t miss opportunities by having minimum nightly stays set to more than three nights. By cutting down your minimum stays, anyone looking for a short last-minute break will still see you in the search results. 

And those short stays can have a significant impact on what you earn. According to research about Airbnb’s minimum night policy, “excluding August, one-night listings earn, on average, 17% more revenue throughout the course of the year.”

List on the right channels for last-minute bookings

There’s only a small window of time to offer discounts and special offers before your listing expires. To capture as many last-minute bookings as possible, you’ll need to act fast and market wisely. Here are some of the best ways to capture more stays before time runs out. 

Advertize last-minute deals on social media

This is a great way to boost direct bookings and spread the word about special offers. Social media channels can be particularly effective when running discounts for referrals. Previous guests will be more likely to share posts with friends and family.

Create a mailing list

You can increase the number of direct bookings you receive by collecting guest email addresses and sending them last-minute promotions.

Airbnb discounts

On Airbnb listings, you can select an option to automatically offer guests a discount on last-minute stays. This is a great feature to take advantage of, especially if you’re offering a discount of 10% or more, as guests will see how much they’re saving and feel more compelled to book a stay. discounts also offers you the possibility of running last-minute deals for your listings. This feature is easy to use and customize. You can determine and set dates, amounts, and other criteria to attract guests.

List on booking websites that target last-minute travelers

Listing your bookings on websites that specifically target last-minute travelers will also help fill those empty blocks in your booking calendar. 

And, as Alex points out, “to have a diverse distribution strategy is probably the most important thing you can do to raise occupancy and revenue and bring new travelers into your space.”

Here are some of the best places to consider listing for last-minute travelers:

  • Whimstay
  • HotelTonight
  • LateRooms
  • Hotwire
  • Last-minute rental groups on Facebook
  • Last-minute deals on Expedia
  • Vrbo last-minute deals

However, listing on every website can be complicated and nearly impossible to coordinate unless you have an STR channel manager. Channel managers automatically update calendars across all booking channels. That way, you can save time posting and updating listings across multiple platforms and protect yourself from double bookings.

Channel managing tools are essential to boosting efficiency while listing across multiple platforms.

Optimize your site for mobile users

According to Google Trends, travel-related searches related to last-minute travel have increased by 519% in the past five years. When it comes to zeroing in on those last-minute bookings, mobile optimization is a website must-have.

Deliver a fantastic experience to last-minute guests

“There’s so much competition out there—it’s so important that owners are unique,” says Alex, “and, if the property isn’t unique, that’s fine. Make the hospitality unique.”

The guest experience is all, so if you don’t have the means to deliver a positive experience to last-minute guests, it’s better to not accept them at all.

On the other hand, if you’re well prepared and ready to take on these bookings, you might receive the kind of appreciation that really sets you apart from your competitors. We’ve included some of the ways that you can better prepare and earn rave reviews from last-minute stays.

Prepare your processes for last-minute turnovers

One of the biggest challenges with last-minute bookings is making sure the property is ready. Alex emphasizes that you need a trustworthy team to help you in these situations.

“I think that it’s incredibly important to find someone that you trust and someone that is really good at what they’re doing.”

Communicating with cleaning staff is one of the biggest challenges while managing last-minute bookings.

As well as hiring the right cleaning staff, you need to be able to notify them about turnovers at a moment’s notice.

The best way to do this is with a reliable task automation system. With a task management tool, you can:

  • Notify your team of last-minute turnovers
  • Automatically update schedules and tasks
  • Create a shared task calendar and send it to your team members
  • Share updates with your team and property owners via email or SMS

Build your message flow around key information

Above all else, guests need to be able to check in without a problem. And as Alex advises: 

“Keep communication consistent and never assume anything. Have a standard operating procedure on how you communicate with guests.”

Here are some key guest messaging best practices to make sure you’re never overwhelmed while providing guests with all the information they need:

  • Use message templates to reflect your voice and style
  • Centralize messages from different listing platforms in one inbox
  • Automate responses
  • Automate review requests after each stay

But a standing operating procedure for hyper-efficient guest communication can’t come at the cost of host-guest rapport: Guests still need to feel they’re communicating with a real person. achieves this with our unique guest experience AI that recognizes questions and instantly crafts a personalized response. This optimizes your response time, allows your voice to be heard, and saves you from being glued to your phone 24/7.

Delight guests with a surprise they’ll love

Provide guests with extra treats to make your hospitality, and their guest experience, stand out.

Small details and extra surprises can really go a long way when it comes to impressing last-minute stays. Welcome baskets or extra amenities are great to have on hand and can make guests feel extra appreciated.

Even better, try leaving guests with local keepsakes or gift cards to nearby restaurants. This is a great way to make them feel welcome while also supporting local businesses.

Make it unique in such a way that they’re gonna remember it and wanna come back. The beauty of it is that everybody has got a unique community, everybody. Take the flavor of that community and put it within the confines of the house…What’s the reason why people love vacation rentals? It’s because they feel like locals

Prioritizing the last-minute guest experience 

Attracting last-minute stays can help you to raise your occupancy levels and revenue. However, creating a five-star guest experience for those stays depends on amazing guest communication and streamlined internal operations. 

Here’s an overview of some of the key strategic factors to help you provide the best experience for last-minute guests:

  • Understand your target audience and the qualities that make last-minute guests different.
  • Make your website mobile-friendly and use social media to promote campaigns.
  • Stay competitive by offering discounts on multiple booking platforms. Using a channel manager will save you time.
  • Provide guests with essential information on check-in and access, and build your message flows around guest needs.
  • Give guests more personalized experiences with small gifts and surprises. Automating your processes and making sure your inventory is stocked with the right items will make this feasible.

With Hospitable’s range of features for automated guest communication, team collaboration, and channel management, you can capture guests you’d otherwise have missed out on, make use of that expired inventory, and deliver a five-star guest experience—even for stays booked on a whim. automates nearly 100% of your guest messaging.

And now, we’re building an end-to-end direct booking solution so you can extend your exceptional hospitality to direct guests.
Start today with a 14-day free trial.
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