About Us


Gertrude Vacation Rentals is dedicated my grandmother, “Gertrude Van-Lopik Jones”, an early pioneer of both adventure and life experience travel, vigorous lover of life, and model for standing above the everyday.

The Story of Gertrude Vacation Rentals

Gertrude Rentals was started on a vacation. It was 2010 on a family trip to Siesta Key in a rental property by a top provider on the island.  Like many others I’d rented, I found a bit lacking. I’m not a fussy traveler and I appreciate that Floridians are on “island-time”, but it took multiple unreturned calls to book and get arrival info all while being passed around to people who couldn’t answer basic questions about things like sleeping arrangements, amenities, or the location. Fast forward to our arrival day, the weather was amazing but it took 30 minutes waiting with young kids to check into a unit that, it turned out, was not exactly like the photos in the listing and had furnishings that were rather uninspired unwelcoming and even gulag-like. We took it in stride and the beach was amazing, but the things we were missing in this rental unit and all the others on the trips before it began piling up in my mind and I went to bed feeling like an unappreciated customer.

The next morning wearing flip-flops and the only collared shirt I packed, I stopped in a realtor open house next door to my rental and just a few months later, closed on the purchase of my first siesta key property. Six months later Gertrude Rentals started with a single apartment listing offering; free cable, free Wifi, free beach chairs, all cotton linens, white-glove cleaning, free late/early checkout/checkin, hand picked furnishings, a first draft “Insiders Guide to the best of Siesta Key”, a no-checkin arrival process, “Matthew” an amazing ambassador-caretaker, and “Dan” (me) a single-point-of-contact for anything from bookings to concierges services to tips and area guides.

Today Gertrude Rentals has 20 seriously sweet vacation rentals, both budget and luxury options, in all my favorite locations; Siesta Key, Spring Lake NJ, and now The Green Mountain National Forest of VT. During the last 7 seasons, I’ve had the pleasure of hosting over 4,000 vacations for groups and individuals, and received thousands of 5-star reviews. I’ve hosted; engagements weddings and honeymoons, 100th birthday parties and 70th anniversary parties, bachelors and bachelorette trips, homecomings for students and for soldiers, vacations for in-recovery adolescent cancer patients and their families, post-op housing for an anonymous kidney donor and a lung transplant recipient, yoga and wellness retreats, single parents traveling alone with kids, family reunions, empty nester getaways, and many others. All of them had one thing in common, they were in search of a well deserved vacation from an owner who understands their vacation time is precious.   –Daniel Jones Super Host and Premier Partner Awards recipient.

–Read More about me, Gertrude, Capt. Allison Jones, Matt, Joy, and our kids below.

My Story “Daniel Jones”

I’ve been a Siesta Key native and a visitor, and now I’m a transplant. I spent the first 20 years of my life on Siesta Key growing up in a bohemian paradise. I ate oranges from trees, caught snook with tin can hand reels and sometimes a cast net, frog-jigged late nights, skipped school to surf hurricane swells, enjoyed beach-hangouts with locals and tourists, collected bay-scallops and stone-crab barehanded, experienced teenage crushes on girls in bikinis, and worked (but just enough to get by). In spite of a soul-feeding upbringing, as a young adult I developed a taste for career advancement and material things and left Siesta Key for New York City to have a career in finance. When I got to “The City”, I worked. I also wore expensive shoes that hurt my broad island-feet, wore ties that hurt my neck, cut my hair, shaved every day, endured a hyper-competitive and sometimes mercenary work environment, and even lost my tan. It wasn’t all work. Once a year I took one weekend off and spent huge amounts of money to travel 4hrs in traffic just to get to a place where a $15 drink is “cheap” and the beach sand and water are so sub-standard I was embarrassed to show it to my childhood friends.

It took 20 years but I came to my senses and left finance. I can’t say for sure what my “wake up call” was, but I think it was the day I received a crate of keepsakes my father sent to my office. In it were typical items like; military medals, childhood photos, old letters and postcards, an American flag, a watch, and some old coins. Also in the crate were a dozen of my grandmother’s (Gertrude) travel diaries. They were brightly colored and exotic, included vivid descriptions and artwork of her experiences, and incredible even unbelievable photos. That day work stopped as my group of 9 senior career finance guys poured over diaries. We started on the desk of the bond trading floor but quickly moved into a spare conference room and eventually “ordered in” lunch. The photos were usually of Gertrude, who was a large 6 feet tall and almost exclusively wore Kaftans and granny glasses, and not just of travels but her in extraordinary situations often in the farthest reaches of the globe.

I only vaguely remembered the photos from childhood, and they seemed too crazy to have really happened, like something I’d just dreamt or imagined. The pictures ranged from Gertrude riding a donkey in the open desert with hat and wig flying in the wind, to her standing arm and arm with nude canibals in the South Pacific, to a hot air balloon ride over Paris on her 90th birthday, to her in the 1950’s behind the wheel of a station wagon with airstream trailer attached somewhere in Mexico and on an unpaved highway alone except for my then 4 yr old father.

That night my group went out and co-workers and competitors talked and drank like brothers. They opened up about things they wanted to do in their lives and never did, their regrets and dreams for the future, until the wee hours of the night. The next day, back in the office, it was business as usual.  All the competition, unconscious materialism, and stress was back. In their defense, I wasn’t exactly transformed either.  It’s hard to walk away from something you sacrificed two decades of a life building (see “golden handcuffs”). It didn’t happen for me all at once.  I became dissatisfied slowly and slowly decided I was at risk of working my life away and committed to changing it.

I mulled over work options like keeping my current position but working less – not possible in finance its all or nothing.  I considered becoming a house-husband – too hard. Forbes said Data Scientists have great life/work balance – are they kidding?  The following Spring I was visiting Siesta Key, staying in a rental that had great reviews but was not that great I thought.  That’s when it occurred to me (literally) that – I’m a guy that can provide every renter with Wifi and parking information, I can stock a house that sleeps four with the right number forks and glassware, and I love family getaways weddings reunions and other events!  That’s it I thought, I should do vacation rentals on Siesta Key!  That weekend I put on my flipflops and the best shirt I’d packed and went to real estate open houses. A few months later I bought my first vacation rental and 6 months after that I said goodbye to the world of finance for good. Make no mistake, I still work like a coal miner from the 1700s, the difference is now I love my job my co-workers and my clients (even my boss), who wouldn’t!  And best of all I get to eat almost every meal with my wife and never miss my childrens recitals, award ceremonies or birthdays.

About Gertrude Van Lopik Jones

Life is a strand of pearls but you never how many are left on your string. – Gertrude.  My grandmother Gertrude made trips to the farthest reaches of the globe well past where civilization stopped, she fully circumnavigating the globe more than a dozen times, and travelled until she was 90. So my grandmother traveled a lot, but she was more than a powerhouse adventurer. She did everything with vigor and had an unstoppable courage and self-determination that made overcoming adversity, often at great odds, part of the adventure. 32 years after her death, she remains our inspiration and guiding light, the spirit of this company.

In Michigan 1939, my grandfather Lawton Allison Jones died, leaving my grandmother, a painter and art teacher at the time, with a 2yr old son.  Gertrude would bury three husbands in all during her life.  Newly widowed, she would use some of the life insurance money to buy manufacturing stocks. With the rest she would buy an airstream trailer, and she soon took over my grandfathers sales route selling industrial lubricants through-out the Midwest, all with my 3yr old father in tow.  The Airstream purchase was the beginning of a wanderlust that would last 50 years for her, and would eventually infect my father, and then myself.

Throughout the 1940s Gertrude sold lubricants and travelled.  A map in one diary logs trips in the year 1941 that included Michigan to Miami, Miami to Illinois, and from Illinois Mexico and Central America. Looking at a photo of her 1942 leaning against the hood of a station wagon with airstream trailer attached somewhere in Mexico and on an unpaved highway alone except for my then 4 yr old father, I cant help thinking, if that’s a dangerous trip today, 70 years ago it must have compared to a moon landing?  Work in progess…….