Our Cape Cod Vacation Rental Management FAQ | Pretty Picky Properties
Chatham & Orleans Properties rent Friday to Friday during Summer Months

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Property Owners FAQ

Property Owners FAQ

  • What kind of advertising exposure will my property receive?

    We believe it’s your Rental Manager’s first responsibility to market your property on its own merits to as many qualified rental prospects as possible. That’s why our single biggest expense is online advertising. We are not content to simply list your property on our website and wait for the phone to ring. We advertise on the most widely used vacation rental advertising portals on the Internet. Places like Homeaway.com, VRBO.com, and Weneedavacation.com. And your property will look its very best, because we take great care and pride in having professional photography, virtual tours and floor plans for most homes. Experience pays off, and our founder, Jim Decker, has 35 years’ experience managing and creating advertising for clients of his own company, Decker Creative Marketing. Once a vacationer inquiry is received, you have a dedicated team which guarantees a quick, professional response – plus attentive service once a reservation is made. It’s a far better guest experience than the call center approach used by some of our competitors. Small wonder that more than 60% of our bookings each year come from returning guests.

  • What do I have to do to prepare my property for summer rentals?

    Musty smelling kitchen cabinet shelf paper that hasn’t been changed since the Reagan Administration doesn’t fly. Portable electric fan blades coated with several seasons of fuzzy grime don’t make the cut. By far the most important single thing you must do is hire a professional cleaning service to do a deep spring cleaning, scheduled as close to your first guest arrival date as possible. It’s now required by Pretty Picky at all properties. It sets the stage for a rental season with fewer headaches. Not to mention more repeat bookings for next summer. If you need it, we will recommend one of the proven cleaning services that we work with on a regular basis. There are many other steps you need to take to properly prepare for the rental season, from supplies to furnishings to safety to amenities. We will email our Pre-Season Property Prep list to you in early spring of each year. The list may seem overwhelming, but we stand ready to help you with a lot of it, as requested. The key is to start your preparations early, long before your first rental guests are due to arrive.

  • I’m worried about damage to my property. How do you approach that issue?

    Instead of a security deposit, we provide an Accidental Damage Protection program. Each rental guest pays a non-returnable fee of $50, for which the program covers up to $1,500 in accidental damage. For higher rental rate properties, it’s a slightly higher fee for more coverage. This provides greater owner peace of mind since the coverage exceeds the amount of a typical security deposit.

  • How much can I expect my property to rent for?

    Our guests are expecting a superior property and vacation experience and are willing to pay more for it. So you can rest assured that we will recommend the best, fair market rate you can expect for your property. We often scan the market so we know what homes comparable to yours have for rental rates. And we will share with you a complete rental analysis, a market savvy presentation of your property’s rental proposition.

  • Do you offer Dynamic Pricing?

    More and more of our owners are signing up for a new, cutting edge pricing tool called Dynamic Pricing. It is similar to the yield management tools that power hotel and airline pricing. Dynamic Pricing sets and manages participating home rates based on a dynamic algorithm that takes into account market-wide supply and demand for every night of the year, as well as comparable market factors particular to a home: amenities, seasonality, day of the week, etc. For the peak summer weeks, we will set the minimum to the rate you have already approved for those weeks. But if the system notices that demand is high for a week you have open, the rates would rise accordingly. In other words, your rate can’t go down, but it can go up for those peak summer weeks.

  • How long have you been rental managers?

    First, we are full-service real estate brokers. We are licensed to list properties for sale, as well as assist prospective buyers in finding their ideal place on Cape Cod. But we choose to focus on select vacation rentals. We’ve been doing that since 2003, shortly after we began renting our own cottage on the beach in Brewster (it’s 078-B here on our website). We could see a real need in the market for a value-added, prime property vacation rentals focus for “picky” owners like us. We also soon discovered that Jim’s, Blake’s & Scott’s marketing and sales experience, coupled with Karen’s organizational and people skills, make us a formidable management team that truly understands the right way to do vacation rentals – from both the guest’s and the owner’s perspective. It’s an approach that has led to impressive growth. Today, Pretty Picky Properties is a full service property management and hospitality team with three offices and a year round staff of nine plus a seasonal staff of more than 50.

  • Do you qualify guests before committing to them?

    We ask a lot of questions and try very hard to be sure a guest group is right for a property, and vice versa, before we send out a rental agreement. Questions include, “How many visitors do you expect during your stay?” and “How many overnight guests will be staying there at any one time?” “How many cars will be parked at the property at any one time?” At your request, we’ll confirm with you before we book any reservation. To streamline the booking process, most owners do not require that confirmation, as long as any guest group adheres to owner approved criteria established from the outset. Again, more than 60% of our guests are returnees, so their performance at the property is already proven.

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