Looking Ahead: Navigating the Future of Short-Term Rentals
3 min

As we conclude the first quarter of 2024, it's a pivotal moment for reflection and forward planning in the short-term rental (STR) market. This year has already shown us the importance of adapting to changing dynamics and capitalizing on emerging trends. With an eye on the rest of the year, let’s explore the current landscape and how Whimstay is strategically positioning itself and its partners for ongoing success.


  • This year brings with it economic uncertainties and the buzz of the election season, impacting international travel and occupancy rates, which are expected to hover around 50%. These factors necessitate a nimble and adaptive strategy for property managers.


  • However, there’s a silver lining with supply and demand in the STR space projected to grow by about 10%. The Gen Z and Millennial demographics continue to fuel travel enthusiasm, with a marked increase in demand for luxury and unique properties. These trends represent significant opportunities for growth and innovation in the sector.

Preparing for Success:

  • How can property managers stay ahead? The focus should be on:
    • Personalizing experiences and sharpening your value proposition to stand out.
    • Diversifying your portfolio to attract new, dynamic audiences.
    • Implementing competitive pricing strategies across all booking windows.
    • Developing a robust last-minute booking strategy to capture the growing trend of spontaneous travel.

Trends in Booking Windows:

  • The trend toward last-minute bookings is becoming increasingly pronounced:
    • 58% of all bookings in 2023 were made within the last 30 days.
    • KeyData reports a 11.4% reduction in US booking windows.
    • This shift is driven by travelers’ confidence in finding options and the prevailing financial stress affecting consumer confidence.

Whimstay’s Record-Breaking 2023:

  • 2023 was a landmark year for Whimstay:
    • Bookings surged by 400%.
    • Gross Booking Value (GBV) increased by 3.5 times.
    • The number of property management partners grew by 2.5 times.
    • Listings doubled.
2023 was a record year for Whimstay

2023 was a record year for Whimstay

  • This momentum is only accelerating in 2024, with Whimstay:
    • Already reaching 1.5 million users year-to-date and on track to hit 4 million in 2024 through partnerships and performance marketing.
    • Achieving 100% direct and organic traffic without any spend on paid media.
    • Onboarding over 1,000 property managers, managing approximately 200k properties.
    • Employing a market-focused strategy and supply partnerships poised to triple our total STR supply by 2025.

Embracing Opportunities, Overcoming Challenges

As we look forward, it’s clear that agility, strategic planning, and innovative thinking will be key. Whimstay is committed to empowering property managers to capitalize on these dynamic trends. By embracing change and leveraging Whimstay’s platform, you’re not just preparing for the future; you’re shaping it. Let’s turn these insights into action and lead the way in the short-term rental industry, together.

Download_PDF_icon Download


Seize the stay! Save up to 60% on vacation rentals.