About

Our History

The Reserve Retreat is a unique property: a boutique hotel with cozy guest rooms; two restaurants- The Café is casual serving American fare for breakfast and lunch; The Reserve Kitchen by Antonio is upscale for lunch and dinner serving Southern European delicacies from land and sea; a Coffee Shop; a Market; and a venue for meetings, parties, or other events. We are independently owned and believe in a culture of diversity, inclusion, equality, and pride.

Two of the three buildings which make up The Reserve Retreat were owned by John Ringling (of circus fame). The homes were used until the mid-1920s when Ringling built his grand estate Ca' d’Zan on Sarasota Bay.

The buildings were moved to their location on Tamiami Trail, then a dirt road. The third building was erected and the compound was used as housing for circus performers and as a practice venue.

In the 1940s, the three buildings and the land they are situated on was known as Parker's Court Camp (a boarding house and inn), operated by Beulah Parker, widow of James Parker. From 1995-2008, these homes belonged to James and Darcy Van Lienden who used the buildings as a photo studio.

Longtime Sarasota resident, Jessica Simmons, was intrigued by the three vacant buildings on the corner of Tamiami Trail N and 14th Street. After inquiring, she was even more enthralled with the history and the potential of the site. A visionary, Jessica saw what could be.

In 2017, after a year of renovation, she opened The Reserve Retreat to guests. In addition to six guest rooms, there was a beer and wine bar and a coffee shop.

“What could be” continues to morph and The Reserve Retreat welcomes guests from near and far. It is a destination with lodging, food and drink, entertainment, and a venue for many types of events and parties.

The Reserve Retreat staff: Owner Jessica Simmons, General Manager Sarah Simmons, and courteous staff members all help create a five-star atmosphere for all guests.

The Owner

Jessica Simmons

Owner Jessica Simmons has been a resident of the North Trail since 1993. About 10 years ago, she noticed the interesting group of buildings at the corner of Tamiami Trail N and 14th Street. Most people would have ignored the eye sores, but they intrigued Jess. After learning the history of the buildings, she decided to rescue them and bring new life to the former home of the Ringling family.

In September 2016, Jess purchased the buildings and began renovating to fulfill her dream. In 2017, The Reserve opened as a boutique hotel. Soon a Coffee Shop was added, and then a kitchen.

Today, The Reserve Retreat boasts two restaurants, six unique rooms on the property, a Coffee Shop, a Market, and a safe haven for all people. Jessica strongly supports a host of community and performing arts organizations. 

Jessica (1)

Recent Honors

2019

Favorite Business

SarasotaOut

2019

Best Guest Accommodations

Sarasota Herald-Tribune Readers Poll

2019

Best Open Mic Night