The High Season Is Coming. Here's How to Supercharge Your STR Listing Now

As the calendar turns toward peak season, property owners managing their own short-term rentals face a now-or-never moment. High season doesn’t wait and neither should you. If you’re hoping to capture maximum revenue, maintain top-tier reviews, and avoid unnecessary stress, this is your opportunity to act with urgency and strategy.

In this column, we’ll dive into practical, proven steps to prepare your STR for the busiest time of year. Each tip is backed by results from real hosts and performance data from successful listings. This isn’t just advice. It’s a revenue blueprint.

Start With First Impressions: Your Listing Photos and Positioning

Your listing photo is your storefront. In a sea of options, the first image is what stops a scroll or loses a booking. If you haven’t updated your listing photos in the last 6–12 months, especially to reflect seasonality, you’re missing out.

Professional photography isn’t optional. It’s foundational. Guests don’t want to guess what the space feels like. They want to see it. Examples from Stronghold-managed properties include:

1. A couple enjoying wine by a fire pit with string lights overhead.

2. Kids jumping into a backyard pool.

3. A holiday breakfast scene on a sunlit dining table.

4. These images do more than show space. They show lifestyle. That’s what books.

Copy That Converts: Talk to the Right Guest

Your headline and description should do more than list features. They should invite a specific kind of guest into a specific kind of experience.

Instead of: “3BR, 2BA home with WiFi and smart TV.”

Try: “Family Retreat w/ Heated Pool + Game Room, 10 Mins from Downtown.”

And instead of writing: “Our home has high-speed internet, a smart TV, and plenty of beds.”

Say this: “Binge your favorite movies on the 65” smart TV, log into Zoom calls with 400 Mbps WiFi, and unwind in a king-size bed after exploring local hotspots.”

Use language that lets the guest see themselves in the space. Use keywords that match what they’re already searching: "family-friendly," "pet-friendly," "near beach," "holiday rental." Update every two weeks to stay algorithm-friendly and visually fresh.

Pricing Isn’t Static. It’s Strategic.

If your rates are the same Monday through Sunday, you’re leaving money on the table. High-performing listings use dynamic pricing tools like PriceLabs or Wheelhouse to auto-adjust nightly rates based on local demand, seasonality, and competitor data.

For example, if there’s a major concert, sports event, or holiday weekend in your area, your rate for those nights should reflect increased demand. One Stronghold client raised their nightly rate by 42% during a festival weekend and booked out completely three weeks in advance.

Minimum night stays should also shift. Weekdays might allow for one-night bookings to fill gaps, while weekends should require two to three nights to maximize returns.

Add discount rules for:

• Early birds (20+ days out)

• Last-minute bookings (3 or fewer days out)

• Weekly and monthly stays

• This isn’t about charging more. It’s about charging smart.

Operational Excellence = 5-Star Reviews

Booking volume increases during high season, and so do operational breakdowns unless you’ve prepared. Most negative reviews stem not from the home itself, but from poor communication, unmet expectations, or missed details.

To avoid chaos:

1. Automate guest messaging with tools like Hospitable.

2. Pre-schedule cleaning and maintenance with a shared calendar.

3. Create a digital guidebook that includes WiFi info, house rules, parking, and local recommendations.

4. Keep backups of all essentials: linens, toiletries, batteries, coffee, and paper goods.

Party-Proofing and Property Protection

More guests mean more risk. Don’t let a single bad booking compromise your reputation or your asset.

Here’s what Stronghold recommends:

1. Require ID verification before confirming any reservation.

2. Use smart tech like NoiseAware for indoor noise monitoring and Ring or Eufy cameras for exterior views.

3. Install keyless locks with code resets between stays.

4. Schedule recorded welcome calls to reiterate guest rules.

5. Have a security contact on standby to respond to major violations.

One Stronghold property in Austin saved over $5,000 in potential damage by detecting a party early via smart noise sensors and responding within 20 minutes to shut it down. Prevention is protection.

Turn Momentum Into Growth

Peak season is more than a cash infusion. It’s your chance to compound growth. Use the income to:

• Fund renovations to improve nightly rates.

• Refinance under better terms.

• Acquire your next property.

• Hire professional help to exit daily operations.

Final Thought: Time Won’t Wait

There is a narrow window to prepare for high season. Once the bookings are coming in, you’re already reacting. The time to set pricing, optimize listings, and strengthen systems is now.

If you’re feeling stretched thin or unsure where to begin, this is your sign to get help. Stronghold clients earned an average of $12,200 per property in 2024 by following a tested system. Not a guess. Not a trend. A system.

Want your STR to become a financial stronghold, not a part-time headache? Book your consultation with Casey today.

Click here to book: https://www.cnvrsnly.com/widget/bookings/turnkeymanagementservices

Because high season favors the prepared.