9 tricks for vacation rentals to get more bookings in the low season

It’s one of the biggest headaches for property owners; getting bookings in mid and low seasons. I’ve been partly involved in the property business for a few years now, and these are just some of the tricks that I’ve learned along the way to boost bookings.

1. Allow for shorter stays 🏁

There are no two ways about it; you have to be more flexible in these seasons. You need to offer lower rates and allow for shorter stays than you would in the high season. Most travelers are savvy enough now to be on the lookout for cheaper and more flexible deals during these seasons, so if you offer a good one you’ll find they get booked up quickly.

2. Create special wellness packages 🌱

Offering packages alongside a booking is a great way to entice potential bookers. A great trick I learned is to research local wellness centres, and offer yoga or spa retreat packages alongside your accommodation.

The new, modern-day focus on wellness makes these popular, and you can work with local businesses who have a social media presence to help you promote these packages.

3. Optimize for countries with low fare rates ✈️

Deals are changing all the time, and it’s worth spending some time researching them. Use Skyscanner to search for flights anywhere from your location for the upcoming months. It will give you a quick look into where the cheapest flights are, and then you can optimize your bookings around this.

For example, if you are based in Lisbon and see that there are cheap flights from Paris to Lisbon all summer, then it would be useful to have a French version of all your vacation rental site listings.

4. Company retreats 🖥️

I started my company Surf Office four years ago with the aim of helping people be more productive in beautiful places. We shifted our focus to help companies with company retreats, and now cooperate with accommodation partners and landlords around Europe.

Our highest demand is in autumn and spring, and so we can now offer these accommodation partners and landlords a perfect proposition where we can help to fill their spaces and rooms in the low and mid seasons.

5. Organize local events 🎪

If your property has a large open space, like a garden or a patio, you can try organizing local events. There is a huge range of events you can think about, like wine tastings, movie nights, or meetups, and you can find local event organizers on places like Meetup.com.

You aren’t always likely to earn money with these local events, but it’s a great way to build up your reputation and create a fantastic relation with the locals. Word-of-mouth counts for a lot in the property business, and they will recommend your properties to friends or relatives visiting them. This is more of a long-term strategy, but it works.

6. Invite bloggers & Instagrammers 📷

This is another strategy which will bring you bookings in the long-term. Bloggers and Instagrammers will create fresh content around your property, which they will share with their peers. Don’t expect direct bookings immediately, especially if you aren’t inviting celebrities with hundreds of thousands of followers.

Try to attract bloggers who aren’t so famous, otherwise, they will charge you for the visit and ask you to cover all of their costs. Smaller bloggers are simply happy with a free stay. You will get some backlinks to your website and probably a few cool pictures to update your listings, and any additional bookings are a bonus.

7. Long-term discounts with weekly/monthly stays 💸

Many sites like Airbnb allow you to set up discounts for a longer stay with weekly and monthly discounts. Avoid them in the high season, when you can fill out your properties easily.

But in mid-low season you can attract people who are searching for longer stays, usually business travelers, digital nomads, students, or teachers. Be aware that these people are very careful with the amenities that regular travelers care about less: equipped kitchen, desk, solid internet, or washing machine.

8. Bundle and unbundle rooms 📦

American entrepreneur and investor Marc Andreessen says that there are “only two ways to make money in business: One is to bundle; the other is unbundle.” You can apply this to vacation rentals too.

Try to be creative with your properties — imagine you have a property with 4 rooms, try to unbundle it into a 4 single room listing. If you manage 10 studios, you can try to bundle them into two, three, four, five studios, and this way attract groups of different sizes.

It may take some playing around to get this right, but it will allow you to appeal to a wider range of people.

9. Contact organizers of local conferences or events 🎤

Research larger events in your area and contact them with an offer to become an accommodation partner. If it’s not a large conference, they don’t usually even ask for commission. This strategy needs a bit of luck to find good partners, but you would be surprised at how many leads to one relatively small event can drive to your business.

And again, it helps with that much-needed word-of-mouth.

Business Ideas & Experiments

Subscribe to my newsletter where I share my experiments of building hospitality businesses.
Well done!
Oops! Something went wrong while submitting the form.

More reading

👋 Hey, I'm Peter and  I'm building a portfolio of niche hospitality businesses.

I have created a marketplace for business group travel. It's called Surf Office.

We help companies to organize offsites, we help hotels to bring group bookings. Almost 1000 hoteliers are subscribed to our Hotel Nuggets newsletter.

Before that, I created the first coworking and coliving space for digital nomads. It went well until it didn't.

Weekend projects 🛠️

Around 2019 I started to play with the idea of building a coworking cabin.

It was my inspiration for Epic Monday - a site full of resources for people who are planning to start a cabin business.

Once I'm passionate about something, I deep dive into the topic, run tons of experiments, and sometimes come up with monetization ideas.

Hoodpicker started as a simple survey, then I created a comparison of neighborhoods in Lisbon, and now it's a set of tools for people who want to invest in real estate in Portugal.

With my latest project, I'm trying to redefine the experience of buying a small hotel in Portugal.

Sharing ideas 💡

I have a small team researching ideas that combine hospitality, real estate, and tech. Some of these ideas I share on this blog.

But I share all of them in my personal newsletter. You can subscribe here:

Well done!
Oops! Something went wrong while submitting the form.

"Your newsletter is the only one I read end to end. You just create no-BS, valuable content. Amazing." - Gui Perdrix

Call for startups 🚀

Are you building something in niche hospitality?

I would love to be involved. I'm mainly interested in:

I can help you with funding and distribution.

Happy to discuss your project over Linkedin or Twitter chat. If you live in Amsterdam, we can meet at the next hospitality coworking day.


"Hi Peter, I have subscribed to your newsletter for a while now and am loving it. The hospitality industry fascinates me and your newsletter always gets my brain to go prrrrrr brainstorming ideas."

- Dário

"Really cool newsletter. Thanks for sharing. Too many interesting ideas to work on."
- Johannes

"Hey Peter, just wanted to reach out to tell you how much i love your posts here. I found out about you through a recent Jakob Greenfeld newsletter, and when i did, i spent hours to read through your previous posts/tweets."
- Cziri

"Just to say that your newsletter is my favorite of all time. I always get so inspired and want to have as many cool projects as you do."
- Margarida

"Very comprehensive. Not working directly on the space anymore, but following your content closely as it is so engaging actionable and without noise 🙏"
- Nico

"Lovely newsletter again Peter! I’m a fan of your ideas and how your brain works.Always sees opportunities ad niche business. Keep up the good work!"
- Sjoerd

"Love your newsletter! The posts are very inspiring and I love how well you break down the business side of it."
- Martin