Stories from the Front Line of Renting my Vacation Home
September 7th, 2007 by TJ Mahony tj@flipkey.comFlipKey was born out of my own experience as a vacation home owner/renter. For the last year I have rented out my Boston condo to people from around the globe. When friends hear of my little side business they are quick with questions:
- Has anyone trashed your place?
- What happens if there is a problem?
- How can you trust a complete stranger?
- Has anyone tried to scam you?
It’s human nature to focus on the negative, but I’m happy to say that my experiences have been 100% positive. I have met people from all around the world that wanted to taste Boston - all have been respectful - and in some cases I have made life long friends.

Moira L.: A wonderful woman from Australia who was in town for four weeks to promote her personal care product line. She called once a week with a general question about the home and then took me out for coffee to say thank you. Moira left my home in better shape than the day I moved in.
Dolores G.: In town for a week to help her daughter find an apartment. I needed to pick up my bike in storage and met them in my home. Dolores had a wonderful family that left behind a bottle of wine to thank me for a great experience.
Elizabeth D.: Arrived in Boston during a cold and rainy Spring week. I was in San Francisco during her family’s stay. Unfortunately my furnace broke down and the family was stuck in my 40 degree condo for 24 hours while I arranged a contractor to replace the broken unit. Elizabeth helped me coordinate letting the contractors in and stayed in good spirits throughout the ordeal. I refunded their last two nights.
The people who have stayed with me have been great, but problems do arise - a broken furnace here and a lost key there. I am fortunate enough to live within 10 minutes of my vacation condo, but my experiences have highlighted the necessity for ‘assistance’. Although occasional rentals can be managed directly by the owner, a seamless experience can only occur if a dedicated service/individual is available for the various mishaps that can occur during a vacation rental.
As renters we have a responsibility to ensure a great vacation experience for our guests. Bad guests do exist, but they are few and far between. Below are my recommendations for ensuring guests receive the support they deserve:
- Use a property manager. Although property managers will charge a 15-30% service fee on the total room rate, they provide end-to-end services that will remove the back breaking chores of cleaning & maintenance and will take care of onsite problems. You get what you pay for, and more importantly your guests will get what they paid for.
- If you are independently renting your home make sure you have a trusted contact within 15 minutes of the home. Your ‘back-up’ should have key access and be aware of when guests are in the home. Should a problem arise your back-up should have previously agreed to manage the situation.
- Before a guest arrives provide them an emergency contact and explain your process in the case of an unfortunate event. If you are a property manager this is a key communication to emphasize the reputation of your service and advantages of using a professional management service.
September 10th, 2007 at 9:09 pm
This is a terrific blog - lots of good stuff and food for thought. You are so right about owners having a local contact; this is so important. Apparently there was a key hidden outside but the owner had neglected to let anyone know.
September 10th, 2007 at 9:12 pm
Most of my previous post got lost - it was about people arriving at a cottage to find the code had been set incorrectly and they could not get at the key. The went home again as they couldn’t get hold of the owner and there was no local contact.
December 15th, 2007 at 9:02 am
very interesting, but I don’t agree with you
Idetrorce