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VR Owner Highlight: Jackie from Boston, MA

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Welcome to our series where we highlight a Vacation Rental Owner and their experiences when they purchased. If you would like to be featured in an upcoming post please send us a message here.

This week we’re talking to Jackie, a licensed real estate agent and vacation rental owner from Boston, MA. She owns a beautiful vacation home in Plum Island, MA and a vacation rental in Savannah, GA. 

Why did you choose to purchase in this location?

I knew they would be good investments.

When you purchased the property was it already a working vacation rental?

No, neither were previously working rentals. They weren’t sold furnished either.

Are you thinking of purchasing another vacation rental property?


Jackie O'Connor - realtor Boston, MA

Would you prefer to purchase a turnkey vacation rental property (i.e. already furnished, with rental history) like one you can find on HighFlyRE?

No, because I want to make it my own and not use someone else’s furniture, etc.

Has your experience as a vacation rental owner been a positive one?

Yes, and I am looking to purchase another one.

Jackie's Plum Island vacation rental - link below

Has your experience as a vacation rental owner been a positive one?

Yes, and I am looking to purchase another one.

When you purchased your vacation rental, did your Real Estate Agent help you evaluate the best options for your needs?

Is there anything more the Real Estate Agent have done to help you with your decision to purchase your vacation rental?

Do you use a vacation rental management company?

No. I manage them on my own.

Do you use any software to manage your rates?


What’s the best part of owning a vacation rental?

Going to vacation at my desired spot and going for free!

If you could purchase another vacation rental where would you buy?

Lake Placid, NY

You can view Jackie’s rental in Plum Island, MA here and Savannah, GA here. And if you’re looking to purchase vacation rental property in the Boston area Jackie is a licensed real estate with in-depth knowledge of the vacation rental market. Connect with her here


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