What self-managing really involves
- Answering every inquiry fast, including the ones that never book.
- Screening guests, writing leases, collecting deposits and returning them.
- Setting rates week by week, and knowing when to adjust.
- Registering with the state, collecting occupancy tax (11.7%, or 14.45% in Oak Bluffs) and filing monthly returns on the rent you collect yourself.
- Booking cleaners and linens for every turnover, and finding a backup when someone cancels in August.
- Arrival instructions, Wi-Fi questions, the broken dishwasher and the lost key, often while you are off-island.
- Keeping your insurance, town registration and inspections current as the rules change.
Done well, it is a part-time job through the whole summer. Done in a hurry, it costs you weeks, reviews and sometimes a notice from the Department of Revenue.
What changes when you hand it to us
- Guests find you. Your home goes on our direct-booking site and the major rental platforms, with professional photos and a listing we write.
- Every inquiry gets answered by a local team that knows your house, and every guest is screened.
- Money and taxes are handled. We collect the rent, file and pay the occupancy tax as your intermediary, and report it to you.
- Turnovers run on schedule, with island cleaners and linens, and photos after every clean.
- You see everything in your private Owner Hub: the live calendar, your rates to approve, house details, documents and a checklist of what’s left.
- You keep your weeks. Block them yourself, straight onto the calendar.
Is it time?
- You have missed a booking because you didn’t answer fast enough.
- You are not certain your occupancy tax filings are right.
- You spend more than a few hours a week on the rental in summer.
- You have scrambled for a cleaner on a Saturday.
- You would rather spend your Vineyard weeks on the beach than on the phone.
If two or more sound familiar, let’s talk. We will walk you through how we would run your home and what you could expect to earn, with no obligation.
Questions we hear
Can I keep my own cleaner?
Often, yes. If they are reliable and you like them, we will work with them and send them the turnover schedule.
What about guests who come back every year?
We look after your returning families and make sure they get their week. Many of our best bookings are repeat guests.
How much does management cost?
It depends on the home and the services you need. We explain our terms clearly on the first call.
Updated October 2026. General information, not tax or legal advice: rules and rates change, so confirm with the Department of Revenue, your town and your own advisor before acting.