About Us - Osprey Vacation Rentals

Commanding a keen mastery of the local real estate market and heeding the call of loyal clients imploring him to expand into the business, Clayton Bonjean, broker-owner of Mainsail Realty Company, teamed up with colleague Cindy Cole to found Osprey Vacation Rentals.

Armed with a marketing degree from Ole Miss and an MBA from UAB, Clayton settled into the Destin area in 1997, where he managed several successful luxury and lifestyle-focused businesses before acquiring and revamping Mainsail Realty Company for the internet age.  Known for more than his expertise, integrity, and owning the area’s top real estate search website, locals often catch him wetting a fine fishing hook or onstage ripping the electric guitar.  At Osprey, Clayton is chief of day-to-day operations, guest relations, and staffing.  A hands-on leader and tech buff, he makes sure that the company is at the forefront of the latest technology trends in the rapidly-changing vacation rental industry.  He is joined by his wife, Katie, a detail-oriented and experienced marketer, in supporting his vision and passion for Osprey. 

Cindy Cole is, bar none, the Destin area's long-standing top luxury realtor.  Previously a serial entrepreneur from Atlanta and New York’s advertising industry, Cindy brings her own globetrotting experiences and expectations to Osprey.  Recognizing a great need for a luxury vacation rental company that didn’t just claim to indulge vacationers and please owners, but that consistently delighted both, Cindy joined Clayton in founding Osprey Vacation Rentals.  Heading up owner relations and marketing for Osprey, Cindy is known for her cordiality, charity fundraising, and relational hospitality.  A connector of people, Cindy introduces many of our owners and guests to the Emerald Coast wine and social scene and is known to throw legendary parties. 

Combined, Cindy and Clayton have sold over $1 Billion in local real estate, the majority of that in vacation rentals. Recognizing a need for extra careful maintenance attention in the vacation rentals management market, they founded Osprey Vacation Rentals.  With a primary focus on maintaining a home’s condition while maximizing profits for the owner, Osprey also aims to enchant their guests with genuine Southern Hospitality. 

Clayton and Cindy are supported by a team of seasoned professionals, but slow and careful growth allows both owners to remain involved in day-to-day operations.  Don’t be surprised if your next owner visit includes a visit from them both, accompanied by a fine bottle of something interesting.