About Us

Often referred to as the “Grand Dame of Rentals,” Judy Michie started in the vacation rental business on Sanibel and Captiva Islands in 1983 and was awarded the Sanibel Captiva Realtor of the Year by her peers without having ever sold a piece of property. She and her husband raised five children in a 1946 beach cottage on Fort Myers Beach and she was instrumental in helping transform Lee County into a top tourist destination.

Judy’s daughter, Sharon, followed in her mother’s footsteps and joined Judy in the vacation rental business after graduating from Cornell University’s School of Hospitality Management and working in the hotel industry for several years.

In 1997, they founded Cottages to Castles – the first boutique rental agency on the islands dedicated exclusively to rentals (not sales). Specializing in offering unique properties and hosting special events, Judy and Sharon were known for providing (almost) legendary personalized attention to properties, owners and guests alike.

After 18 years as business partners and best friends, Judy passed away in 2015 leaving Sharon to continue sharing Judy’s legacy of true Southern Hospitality and Southern Wisdom.

While Sharon is known as the Go-To Vacation Rental Specialist on the islands, she is also a licensed Florida Real Estate Broker and Certified Guest Service Professional.  With her decades of expertise in vacation rental analytics, Sharon is quick to provide guidance to fellow Realtors and Brokers whose clients are interested in purchasing property and offering it as a vacation rental. Remember, “Before you buy an island home, rent.  After you buy an island home, rent it!”

As a born-and-bred native, Sharon continues to live on Sanibel Island and enjoy all-things Sanibel, Captiva, and Florida. She is an outdoor enthusiast, a Licensed Real Estate Broker, and is active with the Sanibel Captiva Vacation Rental Managers Association.

Sharon is also active in the community, particularly with the Sanibel Chapter of the American Legion Auxiliary Girls State program, as well as with the Cornell Club of Southwest Florida. She is also an Affiliate Member of the Sanibel-Captiva Board of Realtors and volunteers with F.I.S.H. of Sanibel (Social Services/Community Food Bank), the Sanibel Captiva Conservation Foundation, C.R.O.W. Animal Hospital and Keep Lee County Beautiful to assist them with their recovery and restoration efforts post-Hurricane Ian. She and her team are working hard to welcome visitors and owners to the islands they affectionately call “Repairadise.”

Besides always having a home improvement project underway, in her spare time, Sharon enjoys fishing, boating, cycling, running half-marathons with her friends and family and; as a former Nationally #1 Ranked cyclist and Lee County Spelling Bee Champion in her youth, she closely follows the Tour de France and the Scripps National Spelling Bee with e-n-t-h-u-s-i-a-s-m! Enthusiasm!

Sharon and the Cottages to Castles Team look forward to welcoming you to our beautiful corner of the world!

Sharon Michie



Judy Michie

1938 – 2015