We’ve all experienced it—that moment when you check your calendar and notice more gaps than bookings. After hosting hundreds of guests over the last few years, I’ve learned that booking fluctuations happen to everyone. Seasonal changes, market shifts, and even unexpected global events can impact your occupancy rates almost overnight.
I wasn’t hosting during the pandemic, but it perfectly illustrates how quickly travel patterns can transform and how hosts need to be prepared to pivot their strategies. While I didn’t face those specific challenges, I’ve navigated my share of booking slowdowns and developed effective approaches to turn empty calendars into profitable stays.
This guide shares practical, proven strategies that have helped me maintain strong occupancy rates even when the market gets tough. Let’s dive into actionable methods to boost your bookings and make your property stand out from the competition. NOTE: There is a lot of information below. Don’t get overwhelmed – just start with a couple of options that you can implement quickly and start seeing results.
Optimize Your Listing
Perfect Your Photography
Professional photos can make a big difference in the number of bookings you get. People make decisions based on photos! If your photos are not high-quality, you will not get potential guests to stop scrolling long enough to learn about the amenities of your property.
- Consider professional photography an investment, not an expense – I’ve seen properties with average furnishings but amazing photos outperform beautifully decorated places with mediocre images.
- Update your photos seasonally – If you have a property with big weather changes – lots of snow in the winter and fields of flowers in the spring – update your photos seasonally to represent those changes.
- Show every room from multiple angles – Guests tell me they appreciate seeing the exact layout and space before booking.
- Include neighborhood photos – The coffee shop two blocks away and the sunrise view from the nearby hiking trail can help tip a guest in favor of your property.
Write a High Quality Listing Description
- Write a compelling headline that highlights your property’s unique selling points
- Use descriptive language that helps guests imagine their stay
- Break text into scannable sections with clear headings
- Highlight proximity to popular attractions, transportation, and amenities
- Be transparent about potential drawbacks to set proper expectations
- Update seasonal information to stay relevant year-round
I have a video on creating your listing description that outlines how to do this using the free version of ChatGPT. You can use it as a starting point to get you going – but be sure to add your own voice to it so it doesn’t sound like AI. The video is linked below.
Refine Your Pricing Strategy
- Implement dynamic pricing based on demand, local events, and seasonality
- Offer weekday discounts to fill traditionally slower periods
- Consider last-minute booking discounts for unbooked dates approaching quickly
- Create special packages for extended stays (weekly/monthly discounts)
- Analyze competitor pricing regularly to stay competitive without undervaluing
- Use pricing tools like PriceLabs, Beyond Pricing, or Wheelhouse for data-driven decisions (full disclosure, I have not used these tools and cannot say for sure which option is best)
Enhance Your Guest Experience
Create Instagram-Worthy Moments
- Design a photo opportunity spot within your property
- Add unique, memorable decor elements that guests will want to share
- Create a beautiful welcome display that guests will photograph upon arrival
- Install statement lighting that photographs well
- Provide branded items that appear in guest photos (mugs, robes, etc.)
- Encourage guests to post and tag your property to create additional awareness
Provide Thoughtful Amenities
- Offer locally-sourced welcome gifts that showcase your region
- Create a coffee and tea bar for guests
- Include unexpected conveniences like phone chargers in every room
- Add experience-enhancing amenities relevant to your location (beach equipment, hiking guides, etc.)
- Consider tech upgrades like smart home features or streaming services
Make It Easy for Guests
- Streamline check-in procedures with detailed instructions and photos
- Create a comprehensive house manual answering common questions
- Provide local recommendations organized by category (dining, activities, shopping)
- Offer flexible check-in/out times when possible
- Respond quickly to all inquiries and booking requests
- Provide multiple payment options if you accept direct bookings
Build Local Partnerships
Establish Strategic Relationships
- Connect with local attractions – I reached out to our area’s popular horse park and built a relationship where they recommend my property to visitors attending multi-day events
- Partner with construction and roofing companies – These businesses regularly need accommodations for clients displaced during home renovations or repairs; I’ve created special rates and flexible booking options specifically for these situations
- Contact project developers and corporate offices – When I learned about a major shopping development project nearby, I proactively reached out to the management company to offer accommodations for consultants, contractors, and visitors
- Offer services to local hospitals – Medical facilities often need housing for traveling staff or patients’ families during extended treatments
- Network with wedding venues – Create special packages for wedding parties for out-of-town family and friends
Create Specialized Solutions
- Develop corporate housing options for businesses with regular visitors
- Design “between homes” packages for people in real estate transitions
- Create custom amenities for specific types of travelers (like providing secure storage for sports equipment for guests visiting for tournaments)
- Facilitate introductions between your guests and local service providers they might need
- Offer insider knowledge that enhances specific visitor experiences
Expand Your Marketing Reach
Diversify Your Booking Platforms
- List on multiple OTAs beyond just Airbnb (VRBO, Booking.com, Expedia)
- Create a property website for direct bookings to avoid platform fees
- Join niche rental sites relevant to your property type (pet-friendly, family-focused, luxury)
- Consider corporate housing platforms for longer-term guests
- List on international platforms popular with travelers from your target markets
Leverage Social Media
- Create dedicated accounts for your property on Instagram and Facebook
- Share behind-the-scenes content of preparations and improvements
- Post guest photos (with permission) and testimonials
- Highlight local attractions and seasonal activities
- Run targeted ads to reach potential guests planning trips to your area
- Join local community groups to promote your property to friends and family visitors
Build Email Marketing
- Collect email addresses from past guests (with permission)
- Send seasonal promotions highlighting what’s special about your property during different times of year
- Create a referral program offering discounts for guest recommendations
- Share property updates and improvements to encourage repeat bookings
- Send targeted offers for dates you typically struggle to fill
Run Promotions and Special Offers
- Create limited-time discounts during traditionally slower periods
- Offer added-value packages instead of reducing rates (include local experiences, wine tastings, etc.)
- Develop loyalty programs for returning guests with progressive benefits
- Bundle services with local tour operators or activity providers for package discounts
- Surprise guests with unexpected upgrades when you have premium inventory available
Target Special Markets
Attract Remote Workers
- Create a dedicated workspace with ergonomic furniture
- Guarantee high-speed internet with backup options
- Highlight your work-friendly amenities in your listing
- Offer extended-stay discounts for “workations”
- Provide office supplies and printer access
- Showcase quiet working areas in your photos
Welcome Families and Groups
- Provide kid-friendly amenities (high chairs, pack-n-plays, toys)
- Create safe outdoor spaces for children to play
- Stock age-appropriate games and entertainment
- Offer baby gear rentals to save families from traveling with bulky items
- Highlight bedroom configurations ideal for different family structures
- Create guides for family-friendly local activities
Improve Your Property
Make Strategic Upgrades
- Add in-demand amenities like hot tubs, fire pits, or outdoor kitchens
- Enhance curb appeal with landscaping and exterior improvements
- Upgrade mattresses and bedding for better sleep experiences and reviews
- Renovate key areas that guests prioritize (kitchens, bathrooms)
- Improve climate control for year-round comfort
- Consider adding unique features that make your listing stand out
Create Seasonal Appeal
- Adapt outdoor spaces for year-round use (covered areas, heating, cooling)
- Add seasonal decorations appropriate to major holidays
- Provide season-specific amenities (sleds in winter, beach gear in summer)
- Update photos to showcase current seasonal appeal
- Create special packages for seasonal activities and attractions
Cultivate Excellent Reviews
Prioritize Guest Satisfaction
- Respond promptly to all guest communications
- Address issues immediately when they arise
- Provide unexpected touches that delight guests
- Follow your guests’ lead when it comes to communication – don’t send tons of messages
- Create personalized welcome notes addressing guests by name
- Remember returning guest preferences
Manage Your Online Reputation
- Respond thoughtfully to all reviews – both positive and negative
- Address criticism constructively and explain improvements
- Thank guests for specific positive feedback
- Learn from patterns in guest comments
- Actively request reviews from satisfied guests
- Showcase review highlights in your listing description
Analyze and Adapt
Track Performance Metrics
- Monitor occupancy rates across seasons and years
- Compare pricing to similar properties in your area
- Analyze booking lead times to understand planning patterns
- Review cancellation reasons to address potential issues
- Track inquiry-to-booking conversion rates
- Assess the effectiveness of different marketing channels
Stay Current with Market Trends
- Join host communities to share insights and strategies
- Follow short-term rental industry news
- Attend webinars and conferences for professional development
- Study successful properties in your market
- Monitor local tourism trends and forecasts
- Adapt quickly to changing traveler preferences
After hosting hundreds of guests over the last few years, I’ve learned that success in the short-term rental business requires creativity and adaptability. The strategies that fill my calendar consistently now aren’t the ones I started with—they evolved through experimentation and response to changing market conditions.
What’s been most effective for me has been thinking outside the typical vacation rental box. Building relationships with local businesses that need housing solutions—from the horse park that brings in regular events to construction companies with displaced homeowners to the management team of a major shopping development—has created booking streams that aren’t dependent on typical tourism patterns.
These partnerships have proven invaluable during traditionally slow periods. When other properties in my area sit empty during the off-season, I often have workers staying for weeks at a time or families waiting for their home renovations to be completed.
Promotions have also been a powerful tool in my arsenal to fill gaps during a typically slow month.
The short-term rental market will always have fluctuations, but with strategic partnerships, creative marketing, targeted promotions, and continuous improvement to your property, you can minimize those slow periods and build a more resilient business. What works for one property or location might not work for another, so don’t be afraid to try unconventional approaches until you find what resonates with your target guests.
Remember that sometimes the most effective strategies come from simply asking yourself, “Who needs housing in my area that isn’t being well-served by traditional accommodations?” Answer that question creatively, and you might just find your calendar filling up regardless of season or market conditions.