Why guests rebook the same property
Four factors drive rebooking decisions, and understanding them helps you design better retention systems.
- Emotional connection matters more than amenities: Guests who’ve stayed at your property already know where the coffee maker is, which bedroom gets morning sun, and how the wifi works. Familiarity reduces travel stress. No research required, no reading 47 reviews, no worrying if photos match reality.
- Trust builds over time: First-time guests take a risk on you. Repeaters already know you respond quickly, deliver on promises, and handle issues professionally. For busy professionals and families, certainty is worth paying for.
- Convenience saves mental energy: Rebooking a familiar property takes minutes instead of hours. Many guests don’t realize rebooking direct saves platform fees while giving better rates.
- Cost benefits add up: Smart managers offer returning guest discounts on direct bookings. Even without explicit discounts, guests save time searching and can plan trips faster.
Rick Armour of RJA Vacation Rentals increased revenue 39% despite losing 30% of his portfolio to regulatory changes. His approach focused on guest experience systems driving repeat bookings through direct channels.
What to send guests before they arrive?
Pre-arrival communication sets tone for entire stays and impacts review scores significantly. Getting the sequence and timing right makes the difference.
Send booking confirmation immediately with property overview and excitement builders. Share your digital guidebook link 7 days before arrival so guests can start planning activities. Building anticipation increases emotional investment in trips.
48 hours before check-in, send logistics:
- Exact address (including GPS coordinates)
- Parking instructions with photos
- Check-in procedures
- Quick-start guide for essentials
On the day of arrival, send access codes and emergency contact numbers. Keep messages short. Guests are traveling and won’t read long emails.
Digital guidebooks answer repetitive questions automatically. Properties using Hostfully’s digital guidebooks report fielding 40-50% fewer basic questions about wifi passwords, parking rules, checkout procedures, and local recommendations.
Amanda from How To Host Kelowna called Linkbase guidebooks integrated with Hostfully “a total game-changer” for creating fully customized guest experiences. Guests check guidebooks at 2am for breakfast recommendations, before booking to evaluate fit, and during stays for answers without waiting for responses.
Set proper expectations to avoid negative surprises. Be honest about property limitations in pre-arrival messages. “Property is on the third floor with no elevator” prevents angry reviews later. “Street parking can be tight on weekends; here’s the paid garage alternative” prevents frustration.
Under-promise, over-deliver works better than the reverse. Guests appreciate transparency. Clear expectations can lead to better reviews even for properties with limitations.
How to personalize communication at scale?
Personalization doesn’t require manually writing every message. Smart data usage and automation structure make it possible to give each guest individual attention while managing dozens of properties.
Track preferences in your property management system:
- Late checkout requests
- Ground floor preferences
- Equipment needs (crib, wheelchair access)
- Amenity usage patterns
Next booking, proactively offer preferences in pre-arrival email. Zero extra time, massive impact.
One manager tracks whether guests use the BBQ, hot tub, or kayaks during stays. Return guests get customized messages: “We restocked the propane and have new BBQ tools since your last visit.” Specific acknowledgment of preferences drives loyalty.
Create message templates for each guest type. Families need different information from business travelers:
Family template mentions:
- Kid-friendly restaurants
- Playgrounds
- Babysitting services
- High chair availability
Business traveler template highlights:
- Workspace setup
- Reliable wifi speed
- Nearby gyms
- Quiet coffee shops for video calls
Hostfully’s unified inbox lets you segment communications automatically based on booking data. Set up once, runs forever. InboxAI (available to customers above the starter package) drafts responses using your property and reservation data, plus guidebook content. Press send rather than writing from scratch.
Camille Maternaghan at Sanctuary Vacation Homes gained back hours daily using smart templates, maintaining personal connections while serving more guests.
Timing matters as much as content. The same message sent at the wrong time is annoying. The right message at the right time delights:
- Mid-stay check-ins work for 3+ night stays
- Post-stay thank you within 2-3 hours of checkout
- Detailed feedback request 3-5 days later
- Special returning guest rate offer 2-3 months later or seasonally
Technology that enables growth without proportional staff increases
Modern STR managers need integrated systems, not disconnected tools. Here’s what actually works.
Smart access management
Hostfully Devices integrates with over 200 smart lock models, including RemoteLock, Lynx, and PointCentral:
- Generate unique access codes automatically for each reservation
- Remotely manage access
- Eliminate key exchange logistics entirely
Properties using smart locks report a 60% reduction in check-in support requests. Visual instructions with photos showing where to park, which door to use, and how to operate locks prevent confusion. One property manager reduced check-in issues by 73% after adding photo-based directions.
Unified communication
Managing messages across Airbnb, Vrbo, Booking.com, direct bookings, and SMS becomes impossible without centralization. Missed messages equal bad reviews and lost bookings.
Hostfully’s unified inbox aggregates all channels into a single interface:
- Nothing slips through cracks
- Your team sees the complete guest conversation history regardless of the booking source
- Set up automated acknowledgment messages, buying time for detailed responses
If the guest messages during the check-in window, the system auto-sends detailed entry instructions. Wifi questions get the password and the troubleshooting guide. Restaurant inquiries get neighborhood food guides.
You only intervene in complex issues. Attention stays on relationship-building conversations rather than answering “What’s the wifi password?” for the 50th time weekly.
Cleaning coordination automation
Turno integration (free for Hostfully users) or Breezeway automatically notifies cleaning teams of check-ins and checkouts:
- No manual coordination
- Cleaners receive task lists
- You get confirmation photos
- Everything flows automatically through the Service Provider Hub
Dynamic pricing integration
PriceLabs or Wheelhouse (offering free Insights to Hostfully customers) adjust rates automatically based on market demand, local events, seasonality, and booking patterns. Managers using dynamic pricing can see revenue increases per property annually.
Chris Miller of Stay Coastal Hospitality turned manual chaos into 34% revenue growth by implementing communication automation. His team maintains personal relationships while managing 3x more properties.
Guest screening and verification
Safely and InsuraGuest integrations protect properties while maintaining a welcoming booking process:
- Screen guests automatically without adding friction
- Truvi (formerly SuperHog) is popular with European property managers
- Autohost offers guest vetting and screening capabilities
Properties by Preston went from 1 to 718+ units in two years using automation for routine tasks while preserving a personal touch for exceptional moments.
Which amenities actually drive rebooking decisions
Not all amenities create equal loyalty. Focus investment on elements impacting rebooking decisions rather than chasing every trend.
Essentials are table stakes (guests expect them, but they don’t drive loyalty):
- Reliable high-speed wifi (minimum 100 Mbps)
- Comfortable beds with quality linens
- Fully equipped kitchen with basics
- Climate control is working properly
- Hot water with good pressure
- Sufficient towels
Nice-to-haves create differentiation and memories:
- Smart TV with streaming services already logged in
- Quality coffee setup with variety
- Board games or books curated to the location
- Local welcome basket with regional treats
- Premium toiletries
- Workspace setup for remote workers
Invest in essentials first. Add nice-to-haves based on your guest demographic.
Local experience curation separates you from competitors
Guests find generic restaurant lists on TripAdvisor. Your insider knowledge can’t be replicated easily.
Create neighborhood guides reflecting genuine local expertise:
- “Best coffee shop for laptop work” beats “best coffee”
- “Family-friendly restaurant with fast service” beats “family restaurant”
- “Romantic dinner spot under $100/couple” gives specific budget guidance that guests appreciate
Properties using detailed local guides in Hostfully guidebooks report 25% higher review scores for “location” ratings.
Partner with local service providers for guest convenience at zero cost:
- Pre-arrival grocery delivery through a local delivery service
- Restaurant reservation assistance
- Activity booking with local tour operators
- Bike or kayak rentals
- Airport transfer connections
Property-specific unique offerings become booking decision factors
Mountain property partners with local ski shops for discount equipment rentals. Beach property provides beach gear (chairs, umbrella, cooler, toys). Urban property creates walking tour guides with historic sites. Lakefront property includes kayaks, paddleboards, and fishing gear.
Guests return because the exact combination exists nowhere else.
Maximizing post-stay retention opportunities
Guest experience doesn’t end at checkout. Post-stay period determines whether guests become one-time visitors or loyal repeaters.
Within 24 hours, send a thank-you while the experience is fresh. Reference something specific about stays. “Hope you enjoyed that coffee shop we recommended” shows you paid attention. Small details create emotional connections, driving rebookings.
3-5 days after checkout, request feedback once guests have settled home:
- What did guests love?
- What could improve?
- Would guests return?
Simple surveys give a goldmine of data for refining operations.
2-3 months later or seasonally, offer a returning guest discount when planning their next trip. Include direct booking links in communications. Many guests don’t realize booking direct saves platform fees. Calculate your direct booking ROI to see potential revenue impact.
Add past guests to simple CRM or marketing automation tools. Send occasional updates about property improvements, local events, or special returning guest rates.
MTM Premier Property Management saw 40% of bookings come from direct and mid-term rentals, perfecting pre-arrival and post-stay communication, making guests feel taken care of throughout the entire journey.
Measuring what’s working in your retention strategy
You can’t improve what you don’t measure. Track specific metrics to understand performance.
Calculate current repeat booking rate
What percentage of guests have stayed before? Industry average is 15-20%. Top performers hit 25-40%.
Formula: (Number of repeat guest bookings ÷ Total bookings) × 100
Monitor response time to guest messages
The average time from guest message to your first response matters. Target under 30 minutes during business hours, under 2 hours after hours. Fast response strongly correlates with review scores and rebookings.
Track review scores by category separately
Cleanliness, accuracy, communication, location, check-in, and value each tell different stories:
- Which scores lag?
- Those areas need attention
- One property with 4.8 stars overall, but 4.3 for check-in focused there and jumped to 4.9 overall
Count support ticket volume and resolution time
How many questions per booking? How long to resolve issues? Declining questions indicate better systems. One manager reduced questions from 8.3 per booking to 3.1 per booking over 18 months.
Measure direct booking conversion rate
Of guests who stayed via OTA first, what percentage book direct next time? Shows how well you’re capturing repeaters into higher-margin channels. Anything above 15% is strong.
Calculate guest lifetime value
Total revenue from repeat guests matters more than single booking value. One guest booking three times at $1,200/stay generates $3,600 in revenue with minimal acquisition cost. Perspective shifts priorities from chasing new bookings to nurturing existing relationships.
Consider taking the business health quiz to identify specific opportunities in your operation. Jasper Ribbers from Overni praised Hostfully’s reporting and customer support for helping analyze metrics.
Key Data offers market intelligence for larger companies needing big analytics. Wheelhouse provides Insights products free to Hostfully customers for forecasting revenue and seasonality trends.
Common mistakes in scaling guest experience systems
Managers scaling operations often hit predictable pitfalls. Avoid them.
Choosing tools before defining processes creates chaos:
- Define your ideal guest journey first
- Map every touchpoint from booking confirmation through post-stay follow-up
- Identify which steps need automation, which need human touch
- Then select tools fitting your process, not the reverse
Over-automating removes personality: Guests can tell when dealing with robots. Find balance between efficiency and authentic connection. Automate routine, personalize exceptional.
Ignoring integration compatibility creates data silos: Your PMS, smart locks, cleaning coordinator, pricing tool, and guest messaging need to communicate with each other. Hostfully offers over 100 integrations, ensuring smooth data flow between systems.
Neglecting team training on new systems wastes technology investment: Your team needs to understand how systems work together. Hostfully University, onboarding webinars, and office hours help teams get up to speed quickly.
Failing to update content regularly makes guidebooks stale:
- Restaurant closed?
- Construction detour?
- New house rules?
Update digital guidebooks once, and changes are deployed instantly to all active guests and future bookings. Set quarterly reminders for seasonal updates.
Creating passive revenue through guidebook upsells
Digital guidebooks do more than answer questions. They create revenue opportunities without additional workload.
Offer early check-in and late checkout through the guidebook:
- Guests browse options at their convenience
- No back-and-forth emails negotiating timing
- Simple add-on purchase during booking or before arrival
Properties report 15% profit increases from passive income without additional workload.
African wildlife sanctuary at Sanctuary Farms captured a 928% revenue increase and a 71% occupancy increase with reliable payment processing through Stripe integration, and guidebook upsells for local experiences.
Partner with local businesses for affiliate-driven revenue:
- Car rental companies
- Tour operators
- Restaurant delivery services
- Spa treatments
- Equipment rentals
Guests get curated recommendations with easy booking. You earn referral fees. Partners get qualified customers.
Linkbase Technologies integration with Hostfully enables AI-powered upsell optimization. The system analyzes booking patterns and guest preferences to automatically push relevant upsells, increasing conversion rates.
Keep upsells relevant to property type and guest needs
Mountain cabin offers firewood delivery and ski equipment. Beach house offers paddleboard rentals and beach setup service. Urban apartment offers parking and restaurant reservations.
Price upsells to provide value while covering costs plus profit margin
Early check-in is typically priced at 15-25% of the nightly rate, depending on the market. Late checkout at 10-20% of the nightly rate. Additional services are priced based on your cost plus desired margin.
Track which upsells convert best. Double down on high performers. Eliminate low performers. Test new offerings quarterly based on seasonal activities and guest feedback.
Building loyalty programs for short-term rental guests
Hotels perfected loyalty programs decades ago. STR managers can adapt principles without complex software.
Offer returning guests 10-15% off when booking directly through your website. Saves you OTA commission fees while passing savings to loyal guests. Win-win economics.
Create simple tiers based on the number of stays:
- Third-time guests get free early check-in or late checkout
- Fifth-time guests get priority booking for popular dates
- Tenth-time guests get a complimentary mid-stay cleaning or a welcome amenity
Give guests who refer friends a discount on their next stay. Word-of-mouth remains the most powerful marketing. Incentivizing creates win-win situations:
- Friend gets a trusted recommendation
- Referring guest gets a reward
- You get a qualified lead
Treat repeat guests differently in communications. They already know your properties and don’t need detailed instructions. Recognize loyalty with personalized welcome messages and small gestures.
Track guest history in your PMS. Hostfully makes it simple with guest profiles, storing preferences, past stays, and notes. Use data to make each stay better than the last.
StayFi integration captures guest information through the Wi-Fi portal for retargeting campaigns, encouraging direct bookings. Guests connect to the Wi-Fi once, and you maintain relationships beyond a single stay.
Programs don’t require complex software. A simple spreadsheet or basic CRM tracks guest history. Automated systems in your PMS trigger different message sequences for new vs. returning guests.
FAQs
How long after a guest stays should I follow up to encourage repeat bookings?
Send a thank-you message within 24-48 hours while the experience is fresh. Follow up with feedback requests after 3-5 days once guests have settled into their homes. Offer return booking incentive 2-3 months later or seasonally when planning next trips. Stay top-of-mind with occasional property updates and special rates for returning guests throughout the year.
What percentage of short-term rental revenue typically comes from repeat guests?
Industry data shows repeat guests can account for 20-40% of bookings for well-managed properties, with higher profit margins due to lower acquisition costs. Top-performing managers achieve 35-45% repeat rates while average operators see 15-20%. Properties with strong guest experience systems consistently reach the higher end of the range.
How can small property managers compete with large companies on guest experience?
Focus on personal touches, local expertise, and quick response times. Small managers have advantages in flexibility and personalized service that larger companies struggle to match. Use automation for routine tasks to free time for relationship building. Your local knowledge provides insider recommendations that large operators can’t offer. The ability to recognize and remember individual guests creates loyalty that big companies can’t replicate at scale.
What’s the most cost-effective way to improve guest experience?
Improving communication timing and quality provides the highest ROI, requiring minimal investment beyond time to set up systems. Create comprehensive digital guidebooks answering common questions proactively. Streamline check-in processes with clear visual instructions. Changes cost little but can reduce support burden while improving satisfaction. Small personal touches like handwritten welcome notes cost under $1 but create an outsized impact on reviews and loyalty.
How do I measure if my guest experience improvements are working?
Track repeat booking rates, guest review scores, response times to inquiries, and direct booking percentages over time. A 10% increase in repeat bookings can impact profitability due to the elimination of acquisition costs. Monitor support ticket volume because declining questions indicate better systems. Survey guests post-stay with specific questions about their experience. Compare metrics quarterly to identify trends and validate which changes drive results.
