Property Owners FAQ

Property Owners FAQ

What kind of advertising exposure will my property receive?

We believe it’s your rental broker’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 each property we list on the most widely used vacation rental advertising portals on the Internet. Places like,, TripAdvisor/ and And your property will look its very best, because we take great care and pride in taking the best photos and crafting the most compelling advertising you’ll see on those sites.

Experience pays off, and Jim has 35 years experience managing and creating advertising for his own company, Decker Creative Marketing.

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

By far the most important single thing you can do is hire a professional cleaning service to do a deep spring cleaning. If you think you can save money by doing it yourself, you’re in for a rocky rental season – and so is your rental manager, who will be the first to field the complaints from your guests.

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. A thorough, professional, pre-season total house cleaning is a must.

It sets the stage for a rental season with fewer headaches. Not to mention more repeat bookings for next summer.

How often do you find it necessary to assess a security deposit for damage or loss caused by a rental guest?

The answer is very seldom. That’s because most of our guests are discriminating in how they choose their vacation rental property and attentive in their treatment of it once they’re vacationing there. But you should understand that some wear and tear from rental guests is inevitable. When you do summer rentals, you’re running a small business that can gross up to $50,000 a season or more, depending on the property and its location.

There will be certain costs of doing business that you cannot expect to pass on to the guests. Accidents can happen – a torn screen, a plugged toilet, an empty propane tank, even a stain on your grandmother’s beloved duvet (which should have been locked away for safe keeping during the rental season anyway). The key is your outlook. If you perceive rental guests as a barely tolerable means of generating extra income, then you should avoid renting like you avoid left turns in August.

But if you adopt the role of an upscale innkeeper, welcoming guests into your home, summer rentals are a pleasant part of owning a second home on the Cape. And the extra cash sure comes in handy!

What if I want to rent only a few weeks?

If we feel you are a Pretty Picky owner and your Cape home is a Pretty Picky property, we’re happy to list it for a few summer weeks only. You’ll get the same attentive service all our owners receive.

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

We’ll always require a security deposit that is refunded after the guests depart, assuming there is no loss, damage or extraordinary cleaning needed. We also offer what’s called “Damage Protection Plans,” for which the guest pays a small, non-refundable premium which covers for up to $1500 in accidental damage. This provides greater peace of mind since the coverage exceeds the amount of a typical security deposit.

Even if you opt for the Damage Protection insurance, we will still require a smaller security deposit to protect against the need for extra cleaning, the single most common reason security deposits are assessed. Here’s another intangible added value Pretty Picky offers to give owners still greater peace of mind: if you or your property manager cannot be on site for rental turnover day, we send our Pretty Picky detailers to the property to execute our Prep Punch List . Sure, we can fail to notice things, but at least with us on the case, you have both the cleaning service and Pretty Picky checking for loss or damage on turnover day.

How much can I expect my property to rent for?

You can rest assured that we will recommend the best, fair market rate you can expect for your property. Often we can command somewhat higher rates, because we’ll advertise your property very aggressively online. Besides, our guests are expecting a superior property and vacation experience and are willing to pay more for it.

How long have you been rental brokers?

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 #78-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 team that truly understands the right way to do vacation rentals – from both the guest’s and the owner’s point of view.

Do you qualify guests before committing to them?

As licensed brokers, we cannot, by law, discriminate based on a number of criteria. However, 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 such as, “How many visitors do you expect during your stay?” and “How many overnight guests will be staying there at any one time?”

And by the way, we’ll confirm with you before we book any reservation if you prefer (most owners do). You’ll know the size of the group, the group configuration (kids’ ages, etc) and you’ll confirm the dates and the rate before the rental agreement goes out. We feel that clear and complete communication with both owners and guests is supremely important and one of our great strengths.

If you do not see your question above, please use this form to ask us. We will follow up with your answer as soon as possible.

Owner FAQ Form