Shahar Goldboim
January 9, 2025
Vacation rentals have existed for many years, offering an alternative to traditional hotels and resorts. However, the way these rentals are marketed and managed has changed dramatically. Early on, owners often relied on pen and paper to track bookings and communicate with guests. Over time, more advanced applications appeared, answering a growing demand for better efficiency and wider reach.
Today, we’re seeing a new wave of tech solutions that use artificial intelligence (AI) to streamline everything from pricing to day-to-day communication.
This article reviews the history of vacation rental software, showing how each stage has paved the way for advanced platforms such as Boom.
Early Foundations: Paper Planners and Basic Tools
In the past, vacation rental management involved little more than a physical calendar and a phone. Owners might mark down dates for arrivals and departures, keep track of cleaning schedules, and make calls to confirm details with upcoming guests. This format was labor-intensive.
A single misread note could lead to booking conflicts, double reservations, or a missed arrival. While this personal approach worked for a handful of properties, it posed problems as businesses grew.
Despite the extra effort required to manage these rentals, the smaller scale made it easier to offer a welcoming experience. Guests often received personalized calls or letters confirming their stays. In many cases, these close connections turned first-time travelers into repeat visitors. However, with shifting travel trends and a growing market, owners began to handle more inquiries.
Keeping up with the added volume using only manual techniques became stressful. Owners started seeking new ways to store data, reduce errors, and keep pace with guest expectations.
Spreadsheets later became a common tool for those wanting something more organized than a handwritten ledger. A spreadsheet was more legible and could be shared quickly among team members. Yet it had its limitations.
People had to manually update formulas, ensure no one else overwrote information, and remember to cross-check the sheet with emails or phone calls. Even if it was simpler to reorder or update data, the risk of human error remained.
The Emergence of Online Booking Platforms
As the internet became widespread, online booking platforms changed the industry. Sites such as HomeAway (later Vrbo) and Airbnb gave owners direct access to travelers looking for unique lodging. Instead of relying on local ads or personal networks, a single listing could attract guests from all around the globe. This broader visibility caused a surge in bookings for many properties, but it also introduced new challenges. Owners found themselves jumping between multiple platforms to keep calendars current and answer messages.
For a time, this was enough to spark significant growth. Many travelers liked the fresh concept of renting a home or apartment rather than booking a traditional hotel. Owners benefited from the constant stream of inquiries rolling in from these websites. However, the day-to-day workload rose. Accepting or declining reservations, confirming check-in times, and coordinating cleaning schedules across multiple sites became a major task.
A key pain point was the possibility of double bookings.
- If a property was listed on three or four platforms, the owner had to update each site whenever a new reservation came through.
- Forgetting to do so even once could mean two sets of guests arriving on the same date.
- Negative reviews followed, leading to headaches and revenue loss.
This situation highlighted a need for more integrated solutions, which led to the next phase of the industry’s development.
The Rise of Early Vacation Rental Software
As online booking portals gained traction, specialized software emerged to help property managers handle tasks more smoothly. These early solutions provided features like
- Centralized calendar
- Automated message templates for guest communication
- Financial tracking
Compared to manual methods, this was a major step forward. Instead of entering the same information on multiple platforms, managers could sync bookings and send out standard check-in instructions with less effort.
These tools were especially welcome for operators managing a few units or more. The immediate benefits included fewer overlooked requests, less double data entry, and more consistent responses to guests.
At the same time, managers still had to oversee several tasks themselves. For instance, they had to guess or calculate nightly rates based on personal observations or local advice, because dynamic pricing was not yet a standard feature. In many cases, owners set a single rate for low season and another for high season, hoping that this guesswork would work out over time.
Reporting features in early software were helpful but often limited. Users might see a chart or a simple data sheet summarizing occupancy over a chosen period. While this overview saved time, it didn’t provide deeper insights into how rates compared with rival properties or whether local events might affect demand. Nevertheless, these early solutions became the foundation for today’s more advanced offerings.
Integrated Systems: Going Beyond Basic Automation
As vacation rental businesses gained momentum, the need for more complex platforms became apparent.
A typical day for a property manager involves:
- Updating calendars
- Checking each property’s maintenance status
- Tracking payments
- Responding to guest questions
Doing all of this across many booking portals was tedious, so developers started creating all-in-one systems. These platforms went beyond basic calendar syncing, offering modules for staff scheduling, payment processing, and real-time performance dashboards.
With these integrated systems, the idea of a single “control panel” for all properties became a reality. Owners could see at a glance how many bookings they had for the coming weeks, what tasks needed immediate attention, and which listings needed price adjustments.
Guest communication improved as well. Instead of manually drafting messages for each inquiry, managers could store and modify templates for common scenarios, such as sending directions and check-in codes. These automated messages could be personalized by inserting guest names or specific details about the property, delivering a feeling of direct contact while saving time. The result was an overall smoother experience that kept the industry moving forward.
AI Enters the Scene: New Levels of Automation
The next major turning point came when artificial intelligence (AI) began to shape vacation rental software. AI allows software to process huge data sets from multiple sources, recognizing patterns that a human might miss.
In the context of short-term rentals, this translates into predictive pricing, accurate demand forecasts, and better management of guest interactions. Instead of picking a one-size-fits-all nightly rate, AI can factor in local events, competitor rates, booking pace, and seasonal trends, then suggest rate changes that adapt to real market conditions.
This approach has allowed property managers to set competitive pricing without constantly monitoring the industry. AI also updates these rates in real time, so there’s less need for manual oversight.
On the guest communication side, AI can answer routine questions automatically, such as providing check-in times or house rules. Only the more complicated cases need a manager’s attention, which is a welcome relief for businesses that handle large volumes of messages.
Moreover, AI-powered systems help owners see beyond raw numbers. By comparing past performance and future forecasts, they can predict periods of high demand and schedule maintenance or upgrades when bookings are usually slow. This knowledge offers a stronger edge in a competitive field. At the same time, these systems gather feedback from every interaction, allowing them to refine their suggestions or responses as user behavior changes.
Learning from the Past to Shape the Future
The history of vacation rental software reveals a progression that mirrors the evolution of the market itself. At first, it was enough to write guest details in a day planner and hope that no one else booked the same slot. Later, digital platforms made it easy to show properties to a wider audience, generating more revenue but also more tasks.
Vacation rental software then simplified tasks by consolidating calendars and automating basic messages. AI has been the latest step, creating an environment where properties are priced in line with actual demand and day-to-day operations run with minimal oversight.
This path underscores how each leap in technology responds to rising expectations from owners, travelers, and marketplace competition. Guests want quick responses and fair rates, while owners want to earn strong returns without losing control of daily tasks. Modern systems meet these needs by merging automation with real-time insights, ensuring that managers can focus on growth instead of micromanaging.
The future of the short-term rental industry is likely to see even more specialization:
- AI may soon manage dynamic marketing campaigns or provide immediate translations for international guests.
- Voice-based interfaces or human-like AI chatbots could become standard features, letting travelers book or request info without ever typing a message.
- Data analytics will keep improving, guiding owners on where to invest in new properties or how to enhance existing ones.
Next Steps for Vacation Rental Software
From its humble origins—penciled-in notes and manual phone confirmations—to the sophisticated AI platforms of today, vacation rental software has followed the needs of a thriving industry. Property managers using Boom experience reduced manual input and faster decision-making, which in turn boosts guest satisfaction and revenue.
Learning from the history of vacation rental software helps us see the progress the sector has made. It also highlights the ongoing drive for greater accuracy and convenience—trends that will shape the next wave of innovation.
With AI’s increasing influence, owners and managers can expect software that continues to refine itself, cut down on repetitive tasks, and deliver an enjoyable experience for both travelers and hosts.
This journey shows that vacation rental software remains a vital tool for anyone aiming to stand out in a busy market, and new inventions on the horizon promise to push the boundary further in the years ahead.
