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šŸ” Tips for Boosting Your Short-Term Rental Occupancy Year-Round 🚨

Slow seasons can devastate your bookings. Use these tips to keep your calendar full all year.

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July 28th, 2025

Good evening STR Report Community!

In today’s issue, you will find:

šŸ“±Today’s Article: šŸš«šŸ” Don’t Let Empty Nights Kill Your STR Income 🚨

šŸ“ˆ Trending Market Highlight: Milwaukee, Wisconsin

🚁 Unique Airbnb of the Week

šŸ« Subscriber Perks: Go Live Playbook, including: Beginner’s Guide E-Book, Guest Communication Messaging Templates, Airbnb Welcome Guide Template, STR Buy Box Template, & Tax Savings E-Book

āœ… Community Perks: Top-Tier Property Management, Personal Airbnb Investment Finder, and STR Loans & More

šŸ“¬ See our collection of newsletters here: Prior Newsletters

šŸ” Tips for Boosting Your Short-Term Rental Occupancy Year-Round 🚨

Owning a short-term rental can be incredibly profitable—but only if your calendar stays booked. Empty nights mean lost revenue, and too many of them can seriously threaten your business. The good news? You don’t have to accept low occupancy as inevitable. Here’s how to keep guests coming in, no matter the season:

Excited Jimmy Fallon GIF by The Tonight Show Starring Jimmy Fallon

Keep your guests coming back like:

1. Identify Your Slow Periods—and Market Smarter


Dive into your booking data to spot the slowest months or weeks. Then create targeted promotions to attract travelers who do book during those times, like remote workers looking for longer stays or locals wanting a weekend escape.

2. Create Irresistible Packages Instead of Deep Discounts


Slashing your rates isn’t always necessary. Instead, bundle in perks—like free early check-in, local attraction tickets, or a complimentary welcome basket—to add value and entice bookings without sacrificing too much revenue.

3. Refresh Your Listing for Each Season


Your photos and descriptions should reflect the current season. Show your cozy fireplace and blankets in winter, highlight outdoor spaces and BBQ areas in summer. Help guests picture themselves enjoying your space right now.

4. Optimize for Direct Bookings


Relying solely on Airbnb or Vrbo eats into your profits. Build an attractive direct booking website, collect guest emails for future promotions, and offer small incentives for booking directly with you.

5. Leverage Local Events to Drive Bookings


Keep tabs on local festivals, sporting events, and conferences. Mention them in your listing and social media posts, and adjust your pricing and minimum stays to capture event-driven demand.

6. Keep Reviews Glowing


Positive reviews are gold for short-term rentals. Wow guests with thoughtful touches and excellent communication, and kindly ask them to leave reviews after their stay. A stellar reputation fuels more bookings.

7. Be Flexible When It Counts


During slower periods, lower your minimum stay requirements to snag shorter bookings that fill calendar gaps. The extra flexibility can help you stay ahead of competitors stuck on rigid policies.

Don’t let empty nights drain your income or put your STR business at risk. Stay proactive, creative, and tuned in to what travelers want—and keep your bookings rolling in all year long.

Milwaukee, Wisconsin šŸ§€

Downloadable Milwaukee, Wisconsin Short-Term Rental Market Report

Milwaukee STR Market Report.pdf2.10 MB • PDF File
  • Average Daily Rate (ADR): $236.07 per night

  • Occupancy Rate: 52.33%

  • Annual Revenue Potential: Around $45,090.85 per year

Read our full Milwaukee, Wisconsin Short-Term Rental Market Report attached above.

šŸ“¬ See our collection of 60+ market reports here: Prior Trending Market Reports

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Subscriber Perks:

šŸ“–šŸ”šŸ’° Go Live Playbook

The "Go Live Playbook" is your all-in-one guide featuring a beginner’s guide e-book, messaging templates, Airbnb welcome book, STR buy box template, and tax savings tips to kickstart your short-term rental success.

Community Perks with The STR Report

šŸ  Top-Tier Property Management ā€“ Lower fees, higher payouts, and premium service. Built for investors who want performance and peace of mind. Act Now: Mention The STR Report by 7/30/25 and get a 6-Month Risk-Free Guarantee.

šŸ”Ž Personal Airbnb Investment Finder ā€“ Connect with an expert to handpick profitable Airbnb properties that match your criteria. With 213+ successful deals, all cash-flowing, you’re in good hands. Take 15 seconds to fill out the form to see how all of these properties are experiencing at least a 15% Cash-on-Cash return.

šŸ¤‘ STR Loans & More – Need funding for your next short-term rental? Expect expert guidance, personalized service, and the best possible rates.

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