By analyzing guest reviews and feedback over multiple years, some clear factors have emerged on why travelers choose to return to their preferred vacation rental properties and destinations. Gaining insight into these decision drivers enables rental owners and managers to tailor their offerings for higher retention and repeat visits.

Discover how and why travelers become repeat guests in this article.

Jump to:

The Comfort of Familiarity
Exceeding Expectations on the First Stay
Building Special Relationships and Personal Touches
Maintaining Quality and Continuous Improvements
Rewarding Loyalty With Perks or Special Attentions
Allow them to book through your own website
Frequently Asked Questions
Key Takeaways

The Comfort of Familiarity

One of the most commonly cited factors for repeat trips is the comfort and familiarity of staying at a known and trusted vacation rental. When guests book a property for the first time, there is uncertainty about what to expect regarding the space, amenities, neighborhood, and overall experience.

Once experienced, familiar properties feel more like temporary homes than impersonal hotel rooms. Returning guests appreciate knowing what to expect in terms of:

  • The layout, size, and furnishings of the rental property
  • Location of bathrooms, bedrooms, the kitchen, and common living areas
  • Operating appliances, electronics, and entertainment systems
  • Quality and cleanliness standards
  • Noise levels and neighborhood quirks
  • Proximity to preferred attractions and conveniences

This familiarity lets guests relax and settle in quickly without unfamiliar elements. Some guests highlight how they appreciate having their preferred bedrooms, quickly finding their way around the kitchen and common areas, and understanding neighborhood norms.

Establishing this comfort and familiarity is a key factor for repeat rental stays.

Exceeding Expectations on the First Stay

Travelers with an extremely positive and enjoyable first experience at a vacation rental property are likelier to return. Their inaugural trip sets the tone for all future stays.

Vacation rentals that exceed expectations, regarding cleanliness, decor, amenities, hospitality, and service, lay the foundation for repeat visits. Strong satisfaction on a first stay also drives word-of-mouth recommendations from guests to their family and friends. This establishes the rental as a top choice for future vacations and trips.

Analyzing guest ratings and reviews shows that guests who rate their first visit 5 out of 5 stars are around five times more likely to book that same property again than those with only average ratings. This demonstrates the importance of ‘wowing’ guests on their first impression.

First Stay Best Practices

Some best practices vacation rental owners use to exceed guest expectations on first stays include:

  • Pre-stay communication: Proactively reaching out before the trip to answer questions, offer local suggestions, and set expectations. This personal touch is appreciated.
  • Arrival gifts: Providing a welcome basket or bag of local snacks, drinks, or gifts surprises and delights new guests.
  • Extra amenities: Stocking bonuses like luxury soaps, high thread count sheets, beach toys and supplies elevate the experience.
  • Effortless check-in: Making arrival, check-in, and entry to the property as seamless and stress-free as possible. Detailed instructions and lockboxes can assist.
  • Cleanliness verification: Performing extensive cleaning, washing, and sanitization procedures before each stay provides peace of mind.
  • Proactive issue resolution: Identifying and quickly fixing any problems or maintenance needs to exceed expectations and build trust.

First impressions go a very long way. Meeting and exceeding initial guest expectations pave the path for repeat visits.

Building Special Relationships and Personal Touches

Some exceptional vacation rental properties have cultivated long-term loyalty by building personal relationships with repeat guests. This is achieved by providing regular visitors with personalized touches and services.

When guests feel like valued individuals instead of just another room number, they are more likely to return year after year. Owners who know their frequent guests’ personalities, preferences, and trip purposes can tailor each stay for maximum enjoyment.

Building bonds through small personalized touches, such as the following, has significantly boosted retention rates:

  • Welcome baskets with the guest’s favorite local snacks and treats
  • Knowing and setting a visitor’s preferred room temperature in advance
  • Remembering if they prefer soft or firm pillows
  • Requesting the same housekeeper
  • Arranging for their preferred interior decorator in advance of annual family trips

Repeat travelers appreciate feeling like the property owner truly knows them and cares about the details that matter most to them. This thoughtful personalization extends special relationships that encourage loyal repeat business.

Maintaining Quality and Continuous Improvements

While familiarity and consistency attract many repeat guests, travelers also want assurance that quality standards are maintained over time. Vacation rentals that offer reliable, high-quality experiences trip after trip have much higher retention rates.

Two key elements of quality over time are:

  1. Consistent cleanliness and maintenance: Guests expect meticulous cleaning, upkeep, and attention to detail during every visit. This builds confidence in the property. Reviews regularly highlight appreciation for consistent cleanliness and presentation.
  2. Continuous improvements: Even when satisfied, guests appreciate seeing upgrades, renovations, and new features that enhance the stay. These improvements signal them that the owner actively maintains and improves the property.

Seeing new bedroom furnishings, added amenities like a hot tub or pool toys, upgraded appliances or electronics, and improved outdoor living spaces reinforces to guests that the experience keeps getting better. It also provides renewed enthusiasm for repeat trips.

Delivering exceptional quality trip after trip, with continuous enhancements, ensures visitors get the best experience every time. The result increases guest retention and referral rates.

Rewarding Loyalty With Perks or Special Attentions

To encourage repeat bookings from loyal guests, some vacation rental companies institute benefits programs that reward return visits. 

For smaller property managers, this might just be personalised gestures such as offering  late check-out for repeat guests, or leaving a note with a small local food or drink to thank them for coming back!

Guest feedback highlights appreciation for the ongoing value they receive as regular returning visitors. Benefits, like progressive discounts, credits for amenities, room upgrades, early check-in/late checkout, and bonus extras, add perceived value that enhances retention rates.

Allow them to book through your own website

To enhance guest convenience and foster loyalty, make it simple for them to book their next stay directly through your own website. By offering the most competitive prices exclusively on your platform, guests have a compelling reason to bypass third-party channels, ensuring they always get the best deal directly from you. 

Additionally, actively communicate your website’s details to guests, providing them with easy access to more information about your property as well as local information, and any special offers. 

This not only avoids channel commissions but also strengthens your relationship with guests by making direct communication and transactions smoother.

With Rentals United, you can create your own direct booking website in just a few clicks! Find out more about My Website 

Key Takeaways

The primary factors that lead travelers to become repeat vacation rental guests include:

  • Familiarity – Returning to known, trusted properties provides comfort and relaxation
  • Exceeding expectations – An exceptional first stay paves the way for repeat visits
  • Personalization – Thoughtful, customized touches build loyalty over time
  • Quality and improvements – Consecutive great experiences with ongoing enhancements demonstrate care
  • Location – Highly desirable destinations entice multiple visits
  • Loyalty rewards – Perks and special attentions for frequent guests increase retention
  • Direct Booking Incentives: Share your website and offer the best direct booking prices maximizes the chances of your guest to repeat

Frequently Asked Questions

What are the benefits of repeat guests?

Repeat guests provide many benefits for vacation rental owners, including:

  • Increased revenues from multiple bookings
  • Reduced marketing costs from less need to acquire new customers- Higher occupancy rates from repeat reservations
  • Lower turnover time and costs from guests already familiar with the property
  • Free word-of-mouth marketing and referrals to the guests’ network
  • Lower risk from guests who you java had a good experience with
  • Ability to develop rapport and tailor service for specific preferences

How can I identify and market to repeat guests?

Strategies to identify repeat guests include:

  • Reviewing historical booking data to see frequent visitor patterns
  • Flagging guests who have booked at least twice before
  • Segmenting your customer email list by repeat vs new guests
  • Analyzing guest reviews to identify mentions of previous stays

Effective marketing tactics include:

  • Sending special offers and promotions exclusively to repeat guests
  • Inviting repeaters to join a formal loyalty rewards program
  • Emailing occasional surveys to identify why they return
  • Showcasing improvements and new features to encourage revisits
  • Using guest photos and testimonials in repeat customer nurturing campaigns

How can I make repeat guests feel more appreciated?

  • Welcome back messages and a special repeat guest arrival gift
  • Handwritten cards or notes thanking them for their loyalty
  • Amenities like snacks, beverages, or treats just for return visitors
  • Loyalty tiers with perks like late checkout, priority booking, etc.
  • Double loyalty points during birthdays or anniversaries
  • Local gift baskets delivered after their visit as a surprise
  • Sending anniversary gifts if they return on the same week every year

The key is showing you recognize and value them as repeat customers.

How can hotels attract more repeat vacation rental guests?

Hotels can attract repeat guests from vacation rentals by:

  • Offering larger suite or apartment-style spaces for extended stays
  • Providing kitchens, living areas, and laundry facilities
  • Giving loyalty program status matches and perks to convert visitors
  • Highlighting unique on-site amenities like waterparks, spas, or restaurants
  • Creating branded residential properties with home-like furnishings
  • Leveraging partnerships with attractions and entertainment
  • Pitching location benefits like walkability to key sights
  • Bundling discounted packages that add value

The key is addressing the main reasons travelers choose vacation rentals: space, amenities, location, and experience.


Gaining repeat rental guests provides tremendous benefits for vacation property owners and managers. It leads to higher revenues at lower marketing costs, increases occupancy, and improves forecasting with consistent bookings.

Understanding the primary factors that motivate repeat visits, like familiarity, relationships, quality, and value, makes programs scalable to maximize retention and loyalty.

Paying attention to the small details that make guests feel appreciated while maintaining high standards trip after trip will encourage repeat business. Travelers are drawn back to properties and destinations they trust to deliver consistently enjoyable vacations time and again.

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