How It Works: Renting Your House

I first met Albert back in the eighties. My then-future wife rented his house in Edgartown one summer and I used to bump into him from time to time. Albert was a little rough around the edges and a bit of a free thinker, but basically a straight-up guy.

When my wife rented his house, he had relocated to a tent out in the woods. Over the years tent living got tedious, so eventually Albert bought a sailboat and would live there when he had tenants. When I bumped into him again down by the dock in Edgartown a few summers ago, I asked if his house was rented and if he was living on his boat. It was indeed, he told me, and he was in fact living on the boat. I looked out at the harbor and asked him which boat was his.

"It's not out there; it's in my yard," he replied. Case in point: yes, there's good money to be made renting your house, but there can also be logistical problems. 

Basically, there are two types of Island rental properties: second homes and those places that are actual year-round residences. The rules of renting apply to both, but as Albert will tell you, it gets a little more complicated when you have to move out.

Madi and Bob Coutts of West Tisbury have rented out their house in the summer for years. “When we first started,” Madi told me, “we’d go away and have a vacation. It was great.” But when their kids got older and had summer jobs, and Bob and Madi needed to be on the Island for work, they fixed up a little guesthouse on the property.

“We planted a row of arborvitae that provided a visual block and it worked out fine,” Madi explained. “We’d just tell the people renting up front that we’d be on the property so there were no surprises. It’s funny, some of the people from the city actually liked having us there.”

If you have no guesthouse and work requires you to be here, you may still be able to profit by relocating to another rental house on the Island. But if you can get away, you can often find a place in Maine, New Hampshire, or Vermont that rents for a fraction of what you’re charging for your house. And then there’s couch surfing.

If your house is a second home or an investment property, you obviously don’t have to worry about moving out. But you might consider renting out your home year-round versus just in the summer. The numbers may come out very close; you might even make more. You avoid dealing with multiple renters and having to close down the house in the winter. You’re also helping local families find housing in an extremely tight year-round rental market.

So how do you go about finding renters? You can try it on your own, use a realtor, or do a little of both. It’s more work, but the advantage of doing it yourself is that you avoid the realtor’s 15 percent commission. What’s more, the Internal Revenue Service allows you to rent your house for two weeks and not pay taxes on the income.

Many Islanders going it on their own advertise on websites like,, or These sites often charge between $200 and $400 per year for the service and can be intimidating; features more than two thousand Vineyard homes. But they do work. You could also advertise in local publications such as the Vineyard Gazette.

The alternative to handling your rental yourself is to go through a realtor. It’s definitely easier that way than doing it yourself. A good realtor will advertise your property, screen tenants, and deal with payments and leases. They may even come in and take pictures of your home for their website. You should interview some realtors to make sure not only that they are a good fit for you, but that you are a good fit for them.

Realtors can’t do it all, however. Darlene O’Neill from Sandpiper Rentals in Edgartown has some tips on making your home rental-ready. Have a cleaning person lined up, and someone to mow the lawn and take out the trash. You also need a relationship with a plumber, an electrician – even an exterminator. If there’s a problem, it has to be fixed immediately. Besides someplace clean and well-maintained, she says, “people are also looking for a good living space where the family can gather – and they really expect a flat screen TV and Wi-Fi.”

When it comes to decorating, O’Neill says less is more. “I don’t think it’s a good idea to have a lot of tchotchkes and family pictures around. A few are OK, but more than that can make it too personal. You should also leave some shelf space in the kitchen in case people want to bring their own pots or pans.”

She recommends having a welcoming packet explaining trash pick up, checkout times, idiosyncrasies about the house, and information on the Island. You can get lots of useful literature at the Martha’s Vineyard Chamber of Commerce. Some homeowners go so far as arranging for ferry tickets, booking them in advance, and passing the costs along. If the tickets aren’t used they’re refundable.

Today, the number of homes for rent on the Vineyard is at an all-time high. “There are a lot more rentals now,” explains Madi Coutts. “We used to have the whole [season] filled by February, but every consecutive summer it seems to get a little harder...there are so many websites and so many people competing, it’s just getting harder.”

Harder, but definitely doable, as the Vineyard becomes more and more of a national, even international, vacation destination. Get your listing out early – many people start booking in January or earlier – and don’t be discouraged, because some people wait until a week or so before they want to come to book.

The bottom line is, it can be a lot of work, but you can make some good money renting your Vineyard house. Plus there’s another fringe benefit: it forces you to fix all those little things that you’ve been putting off for years. u

So, is it worth it?

We asked Lisa Stewart of Lighthouse Properties what a great four-bedroom house might fetch per week in the high season around the Island.

Katama: no water views: $5,000; no water views with a pool: $12,000–$15,000; water views or waterfront with a pool: $45,000.

Edgartown Village: no water views: $8,000–$15,000; no water views with a pool: $20,000; waterfront with a pool: $40,000.

Up-Island: pond views and water access: $15,000; ocean views and water access: $25,000.

West Tisbury: in the woods: $5,000; Deep Bottom area with a pool: $10,000–$12,000.

Oak Bluffs: in town: $5,000–$7,000; Harthaven or East Chop with water views: $7,000–$10,000.

Vineyard Haven: in town: $5,000–$8,000; West Chop waterfront: $10,000–$20,000.

So, should you rent your house? Well, let’s just say that if you’re on the water with a pool in Katama, you might want to think about it.