We’re different!  And better for it!  


Gertrude Rentals is a multi-generation, family business that that includes a wife, husband, daughter, and grandfather.  Named after my grandmother, Gertrude Van-Lopik, who was an adventurous traveler well into her 90s, circumnavigating the globe more than a dozen times.  With boutique vacation rental options in Siesta Key FL, The Green Mountains VT, and Spring Lake NJ, we offer a proprietary vacation property selection to fit any need.  All of our properties are newly furnished, and we only list properties we own.  That makes us 100% responsible for making sure rentals are booked and managed with your comfort and enjoyment in mind.  Please take a moment to read our reviews; we are very proud of them.


We understand your vacation time is precious!  And we know guests come to us for many reasons - to reunite with old friends, develop lasting new memories with your children, treat an overworked loved one to a rejuvenating getaway or to reclaim that part of you that gets buried during the work year.  It’s your vacation, and we want you to get the most out of it.  Shoes, shirt collars and cars are optional, and all our properties are a short walk to the best beaches, recreational activities, shopping, dining and entertainment in Siesta Key and Sarasota.  


Thank you in advance for sharing your love of Siesta Key and the Sarasota Bay areas with us!  


Meet Our Team


Dan, Owner & Director:  Dan is the head honcho around here.  Gertrude Rentals was his brain child, and he left a career in finance to fund and nurture this labor of love.  He was born and raised in Sarasota, and he is proud to say it is the finest beach town, anywhere.  He is passionate about providing affordable beach-luxury during what he calls “sacred vacation time.”  He loves surfing, interior design and Mexican food.  He graduated from the University of South Florida and received an M.B.A. from Fordham University in New York City.  Dan's departure from Wall Street and return to the beaches of Siesta Key represents the hallmark spirit of Gertrude Rentals - no collars, no shoes, no problems!


Matt, Design & Property Manager:  Matt is a native Sarasotan in charge of mantaining the properties, from appliances to accent pillows.  Previously, he was a lead decorator for Nordstrom department stores at their corporate headquarters in San Francisco.  He has extensive training in contruction and repairs, too.  Matt returned to Sarasota to be closer to family and shed his coat and tie.  His practical acumen and astute eye help keep the properties running smoothly and looking beautiful.  His genuine smile and can-do attitude make him a valued team member!


Joy, In-house Counsel & Photographer:  Joy is our legal mind who makes sure everything we do is up to snuff.  She's quick to shake her finger at anything imperfect until it's done right.  She has a notable background in art theory and photographs the properties for the website.  Her favorite activities are spinning and drafting contracts (really).  She impressively holds a B.A. and M.S. from Columbia University, an M.A. from Christie's New York and a J.D. from Penn State Law.


We’d like to acknowledge our figurehead, ships’ captain Allison Van-Lopik Jones, who visited thousands of islands but always insisted Siesta Key was the best!  Also, our youngest family members, Lily and Van, declare Siesta Key is their favorite place in the world, especially in the winter!


Yours truly - The Team!