Loyalty Begins with a Memorable Stay

In the competitive world of short-term rentals, securing a booking is only the beginning. What separates average properties from high-performing ones isn’t just location or price, it’s how guests feel during and after their stay.

Especially in the Azores, where guests come for authenticity and natural beauty, the emotional impact of a warm, thoughtful experience is what truly lasts. And that’s exactly what brings guests back or leads them to recommend your rental to friends and family.

Whether you’re managing your property independently or relying on a professional partner like Your Nest, the key to building guest loyalty lies in small, well-executed details. Let’s look at five that make a real difference and how you can apply them today.

1. Personalised Local Touches That Make a Stay Memorable

Guests don’t expect luxury, they expect authenticity, comfort and care. A small, local detail can completely change the tone of their arrival.

A handwritten welcome note with their names is an old-school touch that always works. A simple gesture like offering local tea, homemade biscuits, or even a single queijada from a nearby café shows that you’re not just renting a space, you’re welcoming someone into a place you care for.

You could also:

• Include a custom mini guide with your favourite local spots (a viewpoint at sunset, a bakery only locals know, your go-to restaurant);

• Provide a regional map with handwritten annotations for hiking routes or swimming spots;

• Leave a postcard of the island and suggest they post it to a loved one, a free memory they’ll associate with you.
  

These touches are low-cost but high-impact. They’re not just thoughtful, they’re what people talk about when they get home.

2. Fast, Friendly and Flexible Communication (Before, During and After)

Speed matters, especially with modern travellers used to instant replies. But tone matters even more.

Guests want to feel like they can count on you, not just “contact support”. Clear, warm and helpful communication from booking to check-out builds trust, reduces anxiety, and helps prevent negative surprises.

Best practices include:

• Pre-arrival: Confirm check-in times, send directions (with a Google Maps pin), let them know what’s included (e.g., towels, soap, washing machine).

• During the stay: A simple “Welcome! Let us know if you need anything 😊” message on the first night makes a big difference.

• Unexpected flexibility: If possible, allow early check-in or late check-out. Guests remember kindness more than strict policies.
  

If you’re not available 24/7, use automated messages, but write them in a way that still feels human.

In reviews, hosts often get 5 stars not because “everything was perfect”, but because they handled small issues well.

3. Make Everything Effortless: Simplicity Is Powerful

Nobody wants to figure out how the hob works after a long flight. Simplicity is key and good information is gold.

Your guests should never feel like they’re “figuring things out”. Anticipate their needs by:

• Providing a printed or digital house guide, in clear English and Portuguese;

• Labelling switches, bins, remotes (with icons if possible);

• Leaving basic instructions near appliances;

• Including info like where to buy groceries, when rubbish is collected, and what’s open on Sundays.

  
  

Also consider:

• Making check-in seamless with a key box or smart lock;

• Having a contact number visible (even if it’s via WhatsApp);

• Explaining the check-out process clearly and kindly.

  
  

The more relaxed your guest feels in the space, the more at home they’ll act and the more likely they are to return.

4. Add One or Two Unforgettable Extras

It’s not about luxury. It’s about surprise and usefulness.

Offer something the guest didn’t expect, but will genuinely appreciate:

• A reusable shopping bag (eco-friendly and practical);

• A small beach kit: two towels, a sun umbrella or snorkel mask;

• A list of “10 restaurants where locals eat”, not the Tripadvisor top 10;

• USB charging cables or adapters;

• A Spotify playlist with Azorean music and fado.

  
  

Seasonal extras work well:

• In summer: fans, picnic kits, bug spray;

• In cooler months: a blanket, local herbal tea, dehumidifier.

  
  

These thoughtful additions turn a “good stay” into a memorable experience and that’s what guests pay forward with reviews, loyalty, or word-of-mouth.

5. Follow-Up: The Detail Most Hosts Skip

Once a guest checks out, most hosts stop communicating, which is a missed opportunity. A thoughtful follow-up after departure can build a relationship, invite feedback, and encourage repeat visits.

What to do:

• Send a thank-you message the day after departure;

• Ask (gently) for a review and offer to host them again;

• Offer a discount code for direct bookings if they come back next year.

  
  

To illustrate this: “Thank you again for choosing us for your Azores adventure 🌿 We’d love to host you again and we always offer returning guests a little bonus! Safe travels 😊”.

Professional property managers like Your Nest can automate this process, but always keeping the tone personal.

A well-timed, kind message can lead to repeat bookings without platforms or commission fees.

Guests Come for the Island, But They Return for You

Yes, the Azores are beautiful. Yes, the landscapes are unforgettable. But in the world of holiday rentals, what makes guests return is how they’re treated.

A clean and functional home is expected. A warm, well-thought-out experience is remembered.

Whether you're managing one property or a portfolio of homes, taking the time (or working with the right team) to create meaningful guest experiences leads to higher occupancy, better reviews, and recurring income.

Want support delivering that level of care at scale?

👉 Discover how Your Nest helps property owners deliver unforgettable guest experiences with ease.

Also read: How to Maximise Your Holiday Rental Income During Peak Seasons

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