About Us

iTrip Vacations Manasota Key is owned and managed by Chris and Wendy Benson. They provide short-term rental owners and guests world-class services in Englewood, Manasota Key, Grove City, Rotonda West, Cape Haze and Don Pedro Island.

About Chris Benson, Owner
Chris Benson built a career as a computer hardware/software engineer, manager, and executive. In these roles, he solved problems in the defense, telecommunications, and cloud computing industries. He has specialized in creating optimal outcomes for customers, professional partners and his team. As a short-term rental manager in Manasota Key, Chris is excited to apply these skills while operating his property management company.

Chris, a Georgia native, earned bachelor’s and master’s degrees in electrical engineering from Georgia Tech University. Chris and his wife and business partner, Wendy, have five children. In his spare time, he enjoys golf, boating and watching sunsets over the Gulf of Mexico.

About Wendy Benson, Owner
Wendy Benson has focused on managing complex IT Software development projects for large corporations. She started as a software engineer and developed experience in managing multi-million dollar budgets for IT projects.

Wendy looks forward to supporting short-term rentals in Manasota Key and Englewood while providing boutique-level service to homeowners and guests.

When not assisting guests and homeowners, Wendy and her sister/general manager, Suzanne Kyre, train for triathlons. Wendy brings her determination and fortitude to drive business and improve short-term rental management services in the area.

About Suzanne Kyre, General Manager
Suzanne’s previous career was in elementary education, and she retired in 2022 from the Community Christian School in Port Charlotte Florida. She has a Bachelor of Arts degree in Elementary Education from St. Leo University and completed graduate work at Liberty University in Christian leadership.

As general manager of iTrip Manasota Key and Punta Gorda, she loves interacting with people and using her skills to meet the needs of vacation rental homeowners and traveling guests. Suzanne and her husband reside in Port Charlotte, Florida, where she enjoys butterfly gardening, triathlons and spending time with her grandchildren.

About Joe Benson, General Manager
Joe Benson comes to iTrip with experience as a North Carolina Real Estate Agent and licensed loan originator.

Joe grew up in Raleigh, North Carolina, and graduated from East Carolina University with a Bachelor of Science in Quantitative Economics. He became a licensed real estate agent in 2020, and became a licensed mortgage originator working as a Loan Analyst and Closing coordinator.

Joe is excited to bring his real estate knowledge and customer service focus to the iTrip team. In his free time, he enjoys training his German Shepard and golfing.

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Questions? Let's talk.

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(941) 977-5353

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iTrip Vacations Manasota Key
13970 Royal Pointe Dr
Port Charlotte, FL

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