Maximizing Last-Minute Bookings in the Short-Term Rental Industry

Meet the Experts

Jamie Lane, Chief Economist at AirDNA, brings deep data-driven insights into the vacation rental industry. In this episode, he's joined by Alex Alioto, Head of Growth at Whimstay, who represents the leading online travel agency (OTA) focused exclusively on last-minute vacation rentals.

Alex explains Whimstay's unique position in the market: "We're the leading last-minute channel in the short-term rental industry. If you're a host, you use us to fill unsold gap nights at the last minute. If you're a traveler looking for a last-minute deal, you go to Whimstay. It's a win-win."

The concept behind Whimstay draws from successful models in other industries. As Alex notes, "Every industry has an overstock model—Nordstrom has Nordstrom Rack. It's an opportunity to make money rather than nothing—found money." This perspective highlights how last-minute vacation rentals represent untapped revenue potential for property owners.

Booking Window Trends and Market Dynamics in 2025

Shortening Booking Windows: Data and Drivers

The vacation rental industry in 2025 faces a dramatic shift in booking patterns. Pre-COVID, typical beach vacation rentals enjoyed booking lead times of approximately 2.5 months—a comfortable window for property managers to plan and optimize their inventory. By 2022, this had already compressed to around 65 nights, still over two months but noticeably shorter. Now in 2025, average booking windows have shrunk below 60 nights, hovering around 55 nights and continuing to decrease.

This compression stems from multiple factors, with economic uncertainty playing the dominant role. Jamie Lane observes, "The name of the game right now is uncertainty." This uncertainty manifests in travelers' reluctance to commit to plans far in advance, preferring to maintain flexibility in an unpredictable economic environment.

Alex Aoto draws parallels between current conditions and the pandemic era: "At the time of COVID, and even now, there's a similar feel—I'll call it 'COVID light.' It's driven more by economic uncertainty than health concerns." This comparison helps property managers understand that while the drivers differ, the behavioral patterns mirror those seen during the pandemic's peak.

The impact on property managers requires significant strategic adjustments. Budget properties experience the most dramatic changes, with a 20% reduction in lead times compared to previous years. This shift demands more agile pricing strategies, flexible inventory management, and a willingness to adapt to last-minute booking patterns.

Traveler Demographics and Behavior Shifts

The Rise of Next-Gen Travelers

Gen Z and millennial travelers have emerged as the driving force behind last-minute vacation rental trends in 2025. These digital natives exhibit distinct travel patterns that reshape industry dynamics. According to Alex, "Gen Z and millennial travelers take about eight or nine trips a year, usually micro-vacations." This frequency far exceeds traditional vacation patterns, creating consistent demand throughout the year.

The work-from-anywhere revolution fundamentally alters how these travelers approach accommodations. "They're working from home, but not their own home," Alex explains, capturing the essence of the digital nomad lifestyle. This flexibility enables spontaneous travel decisions and weekday stays, traditionally slow periods for vacation rentals.

These next-gen travelers show higher check-in rates from Sunday to Wednesday compared to other generations, presenting opportunities for property managers to fill typically challenging mid-week gaps. Their preference for short-term rental experiences over traditional hotels stems from the desire for authentic, Instagram-worthy accommodations that support both work and leisure activities.

Baby boomers represent another significant demographic embracing last-minute travel in 2025. Retirement brings unprecedented flexibility, as Alex humorously notes about his parents: "My parents are retired now, and whenever I see them, they don't even know what day of the week it is." This freedom translates into off-peak travel preferences, with retirees actively avoiding crowded peak seasons in favor of shoulder periods when destinations offer better value and fewer crowds.

Group Travel and Property Types

The last-minute vacation rentals market in 2025 reveals surprising trends in property preferences and group dynamics. Two- to four-bedroom properties dominate the sweet spot, with average daily rates (ADR) between $300-$400 performing exceptionally well on platforms like Whimstay. Alex confirms, "For us, two- to four-bedroom properties are our sweet spot, with an average daily rate of $300–$400."

Perhaps most unexpected is the rise in last-minute group bookings. Traditional logic suggests large group trips require extensive planning, but 2025 data tells a different story. "Logic would suggest a 15-person group trip wouldn't be planned two weeks in advance, but we're seeing it happen," Alex observes. This trend reflects changing social dynamics and the increasing spontaneity enabled by digital communication tools.

Multi-unit properties, condos in vacation destinations, and urban rentals show exceptional performance in the last-minute market. Properties near lakes, mountains, and in city centers particularly benefit from spontaneous booking patterns. The key lies in understanding that last-minute doesn't necessarily mean budget—luxury properties also participate, though typically with slightly longer lead times than the standard 29-day window.

Strategic Approaches for Last-Minute Vacation Rentals in 2025

Platform Diversification and Distribution

Success in 2025's last-minute vacation rental market requires intentional platform diversification aligned with booking window patterns. Alex provides a clear framework: "Different OTAs perform better at different booking windows: Vrbo is strong for 180 to 90 days out, Airbnb for 90 to 30 days out, and we're best for 30 days and under."

This strategic distribution approach ensures properties capture travelers at every stage of their planning process. Vrbo attracts families and groups planning traditional vacations months in advance. Airbnb dominates the mid-range window, capturing both planned trips and those with moderate flexibility. Whimstay and similar last-minute platforms excel at converting unsold inventory into revenue within the final month.

Booking.com typically operates with longer booking windows similar to Vrbo, making it another valuable channel for advance bookings. The key insight Alex emphasizes is intentionality: "Having intention behind your distribution and pricing strategies is key." Random platform selection or hoping for the best no longer suffices in 2025's competitive landscape.

Property managers must resist the temptation to list everywhere without strategy. Instead, understanding each platform's strengths and aligning them with specific inventory segments maximizes both occupancy and revenue. This might mean maintaining premium pricing on Airbnb while offering last-minute deals through specialized channels.

Dynamic Pricing and Revenue Management

Dynamic pricing tools have evolved from optional to essential for last-minute vacation rentals success in 2025. The compressed booking windows demand real-time price adjustments based on market conditions, local events, and remaining inventory. Static pricing strategies leave money on the table and result in unnecessary vacancies.

Maintaining rate integrity across platforms while maximizing last-minute opportunities requires sophisticated approaches. Alex suggests a dual strategy: "You can pair it with Whimstay, so you don't have to show that low rate on Airbnb if you want to maintain rate integrity." This approach preserves brand perception while capturing price-sensitive last-minute travelers.

Expert guidance proves invaluable in navigating pricing complexities. Alex recommends consulting specialists: "Talk to experts like Ben Coleman, who focuses on pricing strategies." These professionals understand market nuances and can help property managers develop pricing rules that automatically adjust based on time to arrival, local demand patterns, and competitive dynamics.

The goal isn't simply filling empty nights at any price—it's optimizing revenue across the entire portfolio. This might mean accepting lower rates for truly last-minute bookings while maintaining premium pricing for properties with strong advance demand. The sophistication lies in knowing when to hold firm and when to adjust.

Marketing and Demand Generation

Attracting Spontaneous and Value-Driven Travelers

Whimstay's 2025 marketing evolution demonstrates how last-minute vacation rental platforms must adapt to reach modern travelers. After years of organic growth, the company launched comprehensive marketing initiatives spanning multiple channels. "We're active on Instagram, TikTok, Facebook, and even have ads on TV Connect, like Hulu," Alex explains, highlighting the multi-channel approach necessary to reach diverse traveler segments.

Social media presence proves particularly crucial for capturing Gen Z and millennial audiences. These platforms are both advertising channels and community-building tools where spontaneous travel inspiration occurs. Visual content showcasing last-minute getaway opportunities resonates with audiences scrolling through feeds and contemplating weekend escapes.

The marketing message must align with the spontaneous traveler mindset. Rather than promoting advance planning, successful campaigns celebrate flexibility, value discovery, and the excitement of impromptu adventures. This messaging shift requires understanding that last-minute bookers aren't necessarily procrastinators. Many people actively choose spontaneity as a lifestyle preference.

Building brand awareness in the last-minute space means educating travelers about the value proposition. Many don't realize significant savings await those willing to book closer to arrival dates. Marketing efforts must overcome the misconception that last-minute equals leftover or inferior properties.

Measuring Incrementality and Value Creation

The critical question for last-minute vacation rental platforms and property managers alike centers on incrementality—are these bookings truly additional revenue, or simply cannibalization from other channels? Alex acknowledges the challenge: "If we're just taking a booking from Airbnb, we're not adding value. One way we've measured it is by talking to our travelers."

Guest interviews reveal a compelling pattern: many trips occur specifically because travelers discover attractive last-minute deals. The value proposition actually induces travel that wouldn't have happened otherwise. Someone browsing Whimstay might see a $180 per night rate in Lake Tahoe and decide to book a spontaneous weekend getaway purely based on the discovered value.

This demand induction represents the holy grail of last-minute strategies. As Jamie notes, "There aren't enough lower prices on weekdays or during the off-season. The hotel industry does this well." Hotels have long understood that empty rooms generate zero revenue, making aggressive last-minute pricing a standard practice. The vacation rental industry in 2025 increasingly adopts similar thinking.

Property managers can measure their own incrementality by tracking booking patterns, guest surveys, and revenue comparisons. The goal isn't achieving 100% incremental bookings. Even partial incrementality justifies last-minute strategies when the alternative is vacant nights.

Emerging Trends and Opportunities in 2025

Domestic vs. International Travel Patterns

The 2025 travel landscape reflects significant shifts in domestic versus international patterns, profoundly impacting last-minute vacation rentals. International travel's decline creates both challenges and opportunities for U.S. property managers. Americans increasingly choose road trips over international flights, driven by persistent high airfare costs and economic uncertainty.

"Airfare remains high, and people are opting for destinations within driving distance to reduce transportation expenses," Alex observes. This shift benefits drive-to destinations disproportionately. Someone in New Orleans might skip Paris in favor of Orange Beach, Alabama. San Francisco residents choose Lake Tahoe over Thailand. These aren't just substitutions—they're deliberate choices favoring accessibility and value.

The absence of international visitors particularly impacts traditionally popular U.S. destinations. Europeans, Canadians, and Asian travelers who once provided steady shoulder season demand now explore other options. However, this gap creates opportunities for domestic travelers to experience typically crowded destinations with more breathing room.

Drive-to markets benefit from another crucial factor: they tend to be more vacation rental-friendly than hotel-dominated destinations. Traditional beach towns, mountain resorts, and lake communities built their infrastructure around vacation homes rather than hotels, making them naturally suited for the short-term rental experience.

Shoulder Season and Off-Peak Travel

The democratization of travel flexibility in 2025 opens unprecedented opportunities for shoulder season bookings. Traditional peak season constraints—school schedules, office vacation policies—matter less when travelers work remotely and retirees ignore calendar conventions. This flexibility redistributes demand across previously slow periods.

"I hope a trend we'll see is people taking advantage of beautiful places when they're not crowded," Alex predicts. His vision isn't mere wishful thinking. Early data shows travelers actively seeking off-peak experiences. Palm Springs in late spring, Park City in mud season, and beach towns in early fall attract visitors who prioritize value and authenticity over peak season bragging rights.

Marketing these opportunities requires education and inspiration. Many travelers don't realize that Telluride's fall colors rival New England's, or that Palm Springs offers perfect pool weather well into November. Property managers who effectively communicate these advantages capture incremental demand that previously didn't exist.

The benefits extend beyond individual bookings. As Alex emphasizes, "If we can spread demand off weekends and peak periods, there's so much potential to grow revenue and occupancy without needing more supply or amenities." This redistribution represents sustainable growth—expanding the pie rather than fighting over existing slices.

Cancellation Policies and Last-Minute Rebooking

Flexible cancellation policies in 2025 serve dual purposes: attracting hesitant bookers and enabling rapid rebooking of cancelled reservations. The interplay between cancellation flexibility and last-minute strategies creates new revenue optimization opportunities. Properties with strict cancellation policies may deter bookings in uncertain times, while overly lenient policies risk revenue loss.

The sweet spot involves strategic flexibility—perhaps offering free cancellation until 7-14 days before arrival, then leveraging last-minute channels to rapidly rebook any cancellations. This approach acknowledges traveler uncertainty while protecting revenue. Platforms like Whimstay excel at converting these last-minute cancellations into bookings, often at rates comparable to the original reservation.

Technology plays an increasingly important role in managing cancellations and rebookings. Automated systems can immediately list cancelled dates on last-minute platforms, adjust pricing based on urgency, and even notify previous guests about newly available dates. This rapid response capability transforms potential losses into recovered revenue.

The comparison with hotel practices proves instructive. Hotels routinely overbook assuming some cancellations, then leverage last-minute channels to fill genuinely empty rooms. While vacation rentals can't overbook, they can adopt similar agility in managing cancellations and converting them into opportunities.

Direct Bookings and Long-Term Industry Health

The relationship between OTAs and direct bookings represents a crucial strategic consideration for 2025 and beyond. Alex offers a perspective that challenges traditional OTA-versus-direct thinking: "Once you get a traveler from an OTA, do everything you can to bring them back direct next time." This approach frames OTAs as acquisition tools rather than permanent intermediaries.

The math supports this strategy. A 5% OTA commission for acquiring a guest who books directly for future stays represents excellent marketing ROI (Return on Investment). The key lies in delivering exceptional experiences that create loyalty beyond platform convenience. This means professional communication, seamless check-in processes, and memorable stays that guests want to repeat.

Industry health depends on maintaining high standards across all bookings. Alex passionately advocates for professionalism: "We need to think hospitality first. If we do, we'll get more direct bookings and capture these travelers." His concern about hosts cancelling for better rates reflects a broader challenge—short-term thinking that damages long-term industry reputation.

The opportunity to capture next-generation travelers won't remain open indefinitely. These digital natives form travel preferences now that will persist for decades. Property managers who deliver consistent, professional experiences regardless of booking source build sustainable businesses. Those who chase short-term gains through questionable practices risk not just individual reputation but the industry's collective future.

The path forward requires balancing multiple channels, maintaining service standards, and viewing each guest interaction as an opportunity to build direct relationships. In 2025's last-minute vacation rental landscape, success comes not from choosing between OTAs and direct bookings, but from strategically leveraging both to build thriving, sustainable businesses.