About Us

Aerial Image of Siesta Key, Sarasota, Florida ,# 1 Beach in America ,99 % Pure Quartz Crystal Sands and The Azure Blue Waters On The Gulf of Mexico

Our business, STAY ON SIESTA, INC. is the result of many years of work in the Hospitality Industry. Our new website is designed to help both Owners and Guests get the maximum benefit from their vacation rental property.

Our web site offers a truly fast and easy-to-use guest experience. Best of all, it features a true, online booking engine just like the Hotel web sites.

It’s our mission to deliver an impressive booking experience, every time.

Service and accessibility are two major parts of our mission. Every guest gets a Marriott-level experience with every stay.

Online booking means we are never closed for business. Our website will accept reservations 24/7.

Guests are welcome to call us anytime to resolve any problem.

Our web site, designed by travel industry professionals, responsively adapts to any device. That means travelers can book their stay on their home computer, tablet or smartphone. And our property management software is considered the gold standard in our industry. It is state of the art, feature rich and powered by the Amazon Cloud. This means travelers looking for vacation rentals on Siesta Key can access it anywhere in the world with 100% guaranteed reliability.


8+ years experience managing our own 43 unit Siesta Key vacation rental property

4 + years of professional hospitality training by an industry expert

15 + years experience renting and owning Siesta Key beach condos

25 + years experience in the family lodging business, managing 135+ rooms and suites

Before founding Stay On Siesta, Inc., Bob and Cheryl each had a professional career. Bob was an electrical engineer for General Electric and GTE Sylvania. Cheryl was an elementary education teacher.

After chasing our original dreams we decided to change careers and join the family lodging business in Massachusetts.

This is where we learned self employment is NOT a 9 – 5 job. Hospitality is in fact, 24 – 7.

More importantly, the cornerstone of our Massachusetts lodging business was to treat every guest as a family and we promise to do the same for your guests.


During those formative lodging business years we vacationed a lot on Siesta. We purchased, remodeled and sold many beach condos.

Like the rest of the world, we fell in love with this tropical island paradise and its beach.

Eventually we sold our business in Massachusetts and relocated to Sarasota, Florida.

We purchased the former Calais Motel on Stickney Pt. Rd., remodeled it and re-positioned it as an upscale vacation rental property, the Hibiscus Suites Inn.

With a lot of hard work, the property enjoyed the status as the # 1 Expedia property in Sarasota, 3 years in a row! It’s Trip Advisor reviews were some of the best on the city.


We are Offering Quality Property Management Services at Reasonable Rates.