How to Maximise Your Holiday Rental Income During Peak Seasons: Practical Tips for Property Owners in the Azores

Managing a short-term rental in the Azores is increasingly seen as a smart way to generate income — especially with the steady growth in regional tourism. But not all months bring the same level of demand, and knowing how to adapt your management strategy to seasonal fluctuations is one of the most important factors in achieving consistent and sustainable returns.

In this article, we explain the typical tourism calendar in the Azores, what sets the high season apart, and share practical strategies that every property owner can apply to make the most of these high-demand periods.

The tourism calendar in the Azores: what seasons are there?

Unlike large cities or beach destinations, where seasonality is more even, tourism in the Azores follows well-defined cycles — shaped by religious events, emigrant flows and the islands’ natural rhythms.

Low season (November to March)

The weather is more unpredictable and demand is lower. However, there are growing opportunities in niche markets such as peaceful nature tourism, workation stays, long-term rentals, and monthly lets. It’s also an ideal time for property maintenance and updates.

Mid-season (April, May, October)

A transition period where many travellers seek to avoid the peak crowds, often choosing longer stays, short cultural getaways, or couple’s retreats. Prices begin to rise, but competition is still manageable.

High season (June to September)

This is the busiest time of year: summer holidays, returning emigrants, international flights and large tourist volumes. Occupancy rates soar, prices peak, and operations become more demanding — but also more profitable.

Religious and festive events

Key dates such as Santo Cristo dos Milagres (May), the Festas do Espírito Santo (June–July), and other local celebrations often create sharp demand spikes, sometimes surpassing the traditional high season in terms of pressure on accommodation supply.
👉 Read our article on Santo Cristo and its impact on tourism

How to make the most of high season: 5 practical strategies for property owners

Now that you understand the seasonal patterns, here’s what you can do to get the best results during peak periods, without unnecessary stress.

1. Plan ahead — the calendar is your friend

Success starts well before the season kicks off.
Good management means planning several months in advance, not just opening the booking calendar at the last minute.

Identify local events, review past demand patterns, and begin preparing both the property and operations to meet the expected increase.
In places like Ponta Delgada, for instance, accommodation for Santo Cristo is often fully booked 4 to 6 months in advance.

Waiting until the season begins often means missing out on income.

2. Set smart pricing — balance profit with occupancy

As demand increases, so should your rates but not blindly. Keeping a flat rate all year is a mistake, but overpricing without justification can also put guests off.

The key lies in using smart pricing tools that adjust rates based on day of the week, demand surges, local events and competitor analysis.

Example: A one-bedroom apartment charging €85/night in April could achieve €120/night during Santo Cristo, and €100–110 in August — with no drop in bookings — when pricing is well-managed.

3. Operational readiness speed, consistency and attention to detail

In high season, response times are shorter and mistakes can cost you dearly. Having well-defined processes for check-ins, cleaning, and guest communication is essential.

Make sure to:

• Use cleaning checklists to maintain quality and avoid oversights;

• Stock up on essentials before the season (extra towels, toiletries, paper goods);

• Perform preventative maintenance (taps, boilers, locks);

• Have contingency plans for late check-ins, last-minute changes, or emergencies.

If operations aren’t well structured, what should be profit can easily turn into stress and negative reviews.

4. Be proactive in guest communication

Guests during peak season often have higher expectations. They want comfort, efficiency, clear information and quick replies.

It's essential to have a well-structured communication plan:

• Use automatic messages before arrival with essential info;

• Offer recommendations suited to the season (events, transport changes, places to book);

• Be flexible with check-ins when possible;

• Provide a simple contact method for emergencies or questions.

Proactive communication builds guest confidence and leads directly to better reviews.

5. Know when (and with whom) to delegate

Managing a rental during high season can feel like running a marathon. If you have just one property, live on the island and have time, it’s possible to do it all yourself although it can be intense.

But if you live off-island, have other commitments, or prefer hassle-free returns, working with a professional management company might be the ideal solution.

At Your Nest, for example, we offer:

• Real-time pricing optimisation;

• Cleaning and maintenance coordination;

• 24/7 multilingual guest support;

• Booking management across multiple platforms;

• Full guest communication and owner updates.

👉 Learn more about our services here

Conclusion: income and peace of mind can go hand in hand

High season in the Azores is full of opportunity for short-term rentals but it also comes with high expectations.
Those who plan ahead, manage pricing properly, streamline operations, and communicate effectively are best positioned to benefit.

And if you'd rather not handle it all yourself, having a local, experienced team at your side could be the difference between a good season… and a great one.
👉 Contact us today and find out how we can help