Jenna Cummings

Jenna Cummings was born and raised on Oahu and now calls Hawaii Island home. She came to real estate the long way around, through hospitality, property management, private aviation and a series of her own businesses, and the thread running through all of it is the same thing that matters most in a transaction: looking after people properly when something important to them is on the line.

Much of her career has been spent looking after property and the people in it. She has managed residential and resort property for Castle Resorts & Hotels at Hali'i Kai at Waikoloa and the Waimea Country Lodge, managed Trailhead Apartments for Cornerstone Property Management, supervised vacation rental onboarding for Elite Vacation Rentals, and looked after guests for Inspirato. That is where she learned what a building actually costs to run, how a rental performs in practice rather than on paper, and how quickly a small maintenance problem turns into an expensive one.

Before that she worked in aviation: operations manager on the private side at Signature Flight Support, a recruiter for SkyWest Airlines, and a flight attendant for Omni Air International. Private aviation runs on schedules that cannot slip and details that have to be right the first time, and she runs a transaction the same way. Dates are tracked, paperwork is ready before it is needed, and nothing important is left to be discovered late.

Jenna is also a business owner several times over. She led the opening and operations of multiple Lilikoi Boutique locations and managed the Cookies Boutique store in Hawaii Kai, and she has built ventures of her own on both islands, including Musik Box Waimea, You + Me Boutique in Waimea, Waimea Lawn and Landscaping at Parker Ranch, and HI Jump Party Rentals in Honolulu. Today she runs Luxrhi Hawaii, which covers luxury guest experience, property maintenance and rentals, alongside The Aloha Friday Co. and the apparel brand Ndgns Hawaii. Having signed her own leases, hired her own crews and carried her own overhead, she is a useful person to have beside you when you are weighing up an investment property or working out what a home is really worth.

Away from work she has spent years in youth sports. She served as president of Hawaii Kai Pop Warner Football, co-owns a Hawaii Youth Sports NFL Flag league, organizes 7v7 programs for Team Fitty and Team Ndgns, and has been involved with the HI Rep Football Academy, a nonprofit football training program. It is the same instinct that shows up in her work: turn up, do the organizing nobody else wants to do, and see it through to the end.

Interior design is a real passion, and it is the part of real estate she enjoys most, because seeing what a property could become is half of helping somebody buy it. Graphic design is her other creative outlet, from team uniforms and posters through to her own apparel line. She has competed in more than thirty pickleball tournaments, including PPA events, and plays at HPA, and when she wants to slow down you will usually find her hunting seashells or working on the family homestead. Creative, resourceful and reliable are the things she wants to be known for, and they are what her clients get.