Starting Strong: More Than Just Bookings

Every year, I meet homeowners who’ve just bought their first rental property in Destin or nearby—and they’re fired up. They’ve read the blogs, seen the Instagram reels, and are ready to earn some passive income.

But after that initial excitement fades, reality sets in: vacation rentals are a business, and they require more than just listing a property online and handing over the keys.

At Gulfview Retreats, we specialize in working with first-time rental owners. I’ve walked dozens of folks through their first seasons, and over time, I’ve noticed a pattern: there are things new homeowners need—but don’t know to ask for.

This post is for you—the first-timers. Whether you just bought your beachside dream or are thinking about turning your home into a rental, here’s what you might not know you need (but definitely do).

1. A Realistic Rental Strategy (Not Just a Price Tag)

New homeowners usually start by asking, “How much can I charge per night?” That’s a good question—but not the first one you should ask.

What you really need:

• A seasonal performance plan (what to expect in summer vs. off-season)
  
• A pricing strategy built around occupancy goals, not just rate
  
• A plan for last-minute bookings, cancellations, and minimum stay rules
  
• Revenue forecasts that factor in cleaning fees, taxes, and maintenance
  

A good property manager doesn’t just toss your place on Airbnb and hope for the best. We study your location, analyze comps, use tools like PriceLabs, and build a custom plan that fits your home and your financial goals.

2. Guest Expectations: The Little Details That Make a Big Difference

Most first-time owners underestimate what guests really expect—and it’s more than clean sheets and a coffee maker.

Today’s travelers are looking for:

• Hotel-level consistency (towels folded, amenities in place, no surprises)
  
• Clear communication (check-in instructions, FAQs, area guides)
  
• Smart tech like Wi-Fi thermostats and keyless entry
  
• Local flavor, like restaurant recommendations or thoughtful design touches
  

What you may not ask for—but should:
A manager who can help set your home up for success, from choosing mattress types to creating a digital welcome book. I work closely with my wife, who’s an interior designer, to help owners strike the right balance between stylish and durable.

3. Home Care Systems That Run on Autopilot

Many new owners don’t think about what happens between guests—but that’s where your property’s reputation is made or broken.

You need:

• A reliable cleaning and inspection team
  
• Systems for restocking essentials (soap, paper towels, linens)
  
• Regular maintenance checks
  
• A plan for last-minute fixes (because a broken toilet at 9 p.m. is not fun)
  

We use Breezeway to manage all our turnover tasks and maintenance scheduling. You shouldn’t have to chase your cleaner or guess whether the AC filter’s been changed.

Ask your manager: “What’s your operations system? How do you track cleaning and repairs?”

4. Transparent, Friendly Communication

Too many first-time homeowners assume they’ll just get a check each month and maybe a report. But the best relationships are collaborative and transparent.

At Gulfview, we believe in:

• Monthly performance reports (revenue, occupancy, reviews)
  
• Photos after cleanings or maintenance issues
  
• Upfront conversations about negative reviews or guest complaints
  
• Being available for your questions—no matter how small
  

You should feel like you’re part of a team, not just a number on a spreadsheet.

5. Education & Guidance Beyond the Basics

New homeowners don’t always realize how much there is to learn about the rental market—taxes, insurance, licensing, local ordinances, guest screening, cancellation policies… it’s a lot.

That’s why we run homeowner seminars a few times a year. We cover:

• Local regulations and what’s coming down the pipeline
  
• How to interpret performance metrics
  
• Tips for property upgrades with the best ROI
  
• How to build long-term value, not just quick bookings
  

Even if you’re not a client, I always encourage owners to ask questions and stay curious. A good manager should act as your guide—not just your booking agent.

6. An Advocate in the Community

One thing most owners never think to ask for: a manager who’s locally rooted and connected to the Destin business community.

We work closely with local vendors, attend Chamber of Commerce events, and stay in touch with city officials. That gives us an edge when:

• Navigating permit or regulation changes
  
• Sourcing trusted vendors for emergency repairs
  
• Recommending reputable services to guests or homeowners
  
• Staying ahead of tourism trends and market shifts
  

You’re not just hiring a manager—you’re tapping into their local knowledge, network, and reputation.

Ask More, Expect More

If you’re just getting started with your vacation rental, congratulations—it’s a fun and rewarding journey. But don’t sell yourself short by only asking surface-level questions.

Ask your property manager:

• “How will you help me grow?”
  
• “What systems do you have in place for care and communication?”
  
• “What happens when something goes wrong?”
  
• “What does your support look like in the off-season?”
  

The more you ask, the better you’ll understand what kind of partner you’re hiring. And trust me—when your property starts running like clockwork and your guests leave 5-star reviews, you’ll be glad you took the time to ask the right questions.

And if you’re ever in Destin and want to chat over coffee or a Gulf breeze, I’m always happy to share what I’ve learned.