In Jim and Jessica Wood’s first Summer as owners of iTrip Boston and South Shore, a full-service short-term rental property management company, every property from the South Shore beaches to Boston suburbs was pretty much booked solid with guests. Jim and Jessica manage a wide portfolio of properties—ranging from 2-bedroom cottages and condos, to large luxury homes with every amenity that guests are looking for.

Jim and Jessica are eager to grow their business by partnering with investment property owners across Boston and the South Shore while using their knowledge of the region and their people-first personalities to provide their clients and guests top-tier service. Jim, with his background in accounting and financial services, and Jessica, with her experience in healthcare sales have put their skills into practice for the iTrip Boston and South Shore market beginning in March of 2022. 

They partner closely with the real estate community on the South Shore and are looking to build lasting referral relationships.  Within their large network of realtors, those who work with them are awarded ongoing lucrative commissions for each referral that Jim and Jessica sign. 

They’ve built strong relationships and want to help realtors close even more sales in the investment property sector by providing insight into revenue potential and the local market. 

“Our goal is to maximize our clients’ profits, while also providing our guests the best travel experience. We pride ourselves on being collaborative with owners, treating their properties like our own, and the guests like our family.”

Jim and Jessica credit their success managing short-term rentals to the quality of the properties and the care they put into their elite guest services. Jim says, “We’re always looking to give the personal touch, so that guests are inclined to leave a 5-star review. We want people to feel welcome and have the best stay possible.”

When a homeowner works with iTrip, they will receive full-service rental management from onboarding, marketing, cleanings, property maintenance, and guest services. “It’s an honor to showcase our clients’ homes in an area we both love so much.”  They ensure their clients have as much or as little involvement as they wish. Part of the marketing includes ensuring that a listing is pushed out to more than 85 websites, with all the big names in the rental industry, like Airbnb, VRBO, Booking.com, Marriott, Trip Advisor, and many more. 

Professional photography, 3D Matterport tours, and managing the guest experience from booking to check-out are all services that iTrip customizes based on the needs of their property owners. “We work with a variety of clients, from those who use their home for partial periods of the year, to investors looking to maximize their rental revenue. Some of our clients live out of state and we manage their homes entirely, while others live nearby or next door and may have some involvement, but want to take advantage of our industry-leading marketing and guest services.

“A large part of our success with our homeowners is valuing communication and transparency,” says Jim. iTrip provides an owner portal, detailed monthly financial statements, and control over blocking the calendar for their own use.  The husband-and-wife team are life-long Massachusetts residents, both attending college here also. Well before they even knew each other, Jim’s Mother was even Jessica’s middle school teacher. They attended the same high school and are now raising their 2 children in the area around family and friends they’ve known forever.  They’re an avid New England sports family and enjoy hosting and entertaining.

Our guest services start with curiosity to tailor the experience, asking guests what inspires their stay. “Once we had a group with expectant mothers, so we made sure there were snacks, cookies, pickles—anything a pregnant woman might want,” Jessica says. “We look for that individual connection, champagne for an anniversary, a treat during a holiday, or a thank you note to a return guest.”

So if you personally have an investment property, know of a client or friend in need of management, or have properties for sale that would be a good fit for short-term renting -- reach out to Jim and Jessica Wood with iTrip Boston and the South Shore!