How ‘Rather Be Properties’ Upsells Success with Hostaway

Like most short-term rental businesses, Rather Be Properties started out small. Owner Al Sed bought two vacation rental properties in 2021. His wife and partner Elissa ran the business while Al worked full-time in residential lending. 

As anyone in the space will tell you, residential lending is a grind. So Al made a big change — he retired from his full-time gig and, in 2023, put all his professional focus and attention on Rather Be. 

Today, they run 34 active listings across California, North Carolina, Arizona and more. Beyond being a standout Hostaway user in every which way, Rather Be Properties has tapped into a lucrative, additional revenue stream — upsells. 

This is the story of Rather Be Properties’ success, thanks in part to their dynamic upsell strategy. 

Rather Be Properties Bio

• Founded: 2021

• Headquarters: North Carolina, US

• Locations: California, North Carolina, Arizona and more

• Listings: 34 active listings, 5 more coming soon

• Employees: Al & Elissa Sed + 7 full-time employees, plus contractors

• Started with Hostaway: Feb 2023

Living by Their Mission Statement

Delivering five-star hospitality to guests while maximizing owner profits. That’s the goal, that’s the mission. And it’s what sets Rather Be apart from the competition. 

“It’s hard to do both and we’re not perfect. But that’s the north star we follow and we believe that’s what sets us apart.” says Al. 

Rather Be does it all. They’re a full-fledged property management and co-hosting company for brand new listings, agency- and owner-managed properties. When it comes to their services, there’s virtually nothing they don’t offer. 

From the nitty-gritty details of finances and accounting to the art of interior design, OTA channel management and more, it’s this full-suite of services that’s helped Rather Be achieve the success it has. 

Working with Hostaway

Every short-term rental company gets to a stage in its growth trajectory where a little vacation rental software is needed. Not only to accommodate more listings across more channels, but to help onboard a growing staff. 

Since Rather Be signing on as a Hostaway customer in February 2023, Hostaway has become their hub for everything. Chief among all the things Rather Be relies on Hostaway for is OTA channel management, in addition to guest messaging, listing management and optimization, and integrations. 

Where Rather Be shines in the world of Hostaway customers is in their upsell strategy. They started adding upsells a year ago and the results speak for themselves.

Upselling Their Way to Success

Early check-in and late check-out were the first areas of opportunity for upsells. It was one of the most frequent requests made by guests, and the potential for monetizing accommodating these requests was obvious. (Pool heating and pet fees were also identified as popular upsells). 

The guests had little hesitation about paying for these upsells. Around half of all guests would book and pay for the upsells without asking about it, resulting in immediate extra revenue. 

The problem though was an operational one. Rather Be was manually sending upsell options through Airbnb. So when Al and team wanted to offer upsells across all OTAs, things became very complex. That’s where the power of Hostaway flexed its muscle again. 

With Hostaway, Rather Be could easily incorporate upsells through OTAs that didn’t have native upsell capabilities. Upsells were now added as part of the online check-in form in Hostaway for all reservations. What’s more, Rather Be branched into amenity-related upsells like offering a silent disco set and paddleboard rentals. 

More Money, Less Problems

In just four months from January to April 2024, Rather Be generated more than $40k in upsell revenue (around $300-$400 a month for each listing with early check-in alone). They started with $50 and slowly raised the fee to $75, seeing no noticeable drop-off after the price hike. Al and team already see additional upsell opportunities when it comes to amenities they’ve yet to monetize. 

Of course how they monetize amenity and other upsells can be a delicate balance. Al says that property and price point matter when it comes to the willingness of guests to pay for certain upsells. “Make sure the value is already there on your nightly rates before charging more for add-ons.” 

Beyond assessing a guest’s willingness to pay for upsells, Al cautions short-term property managers to be thoughtful before entering the world of upsells. If you’re going to promise — and charge for — extras, businesses need to make sure they can actually handle the promises being upsold. 

Upsells Can Be Your Ticket to Boosting Revenue

It’s not like upsells with Hostaway will turn a mediocre business into a world-class operation overnight. Rather Be Properties has been honing their craft, offering a five-star experience for almost three years now. It’s this attention to detail and commitment to excellence that has allowed them to benefit from Hostaway’s upsell feature, they had to walk before they ran. 

Nonetheless they are a prime example of the value short-term rental operators can unlock through thoughtful, meaningful upsells. The guest gets a better experience and the business ends up with more money in their pocket. 

A win-win situation like this one will ensure Rather Be is a force to reckon with in the vacation rental space for years to come.