The Reserve Retreat is a unique property. It contains a boutique hotel with cozy guest rooms for nightly, weekly and monthly stays. Our restaurant serves American-fare, in a casual fine dining atmosphere. The beer/wine bar with large selections and coffee shop are favorites of guests and neighborhood regulars. Many people know us as a venue for live music, and we provide space for meetings, parties, or other events. We are independently owned and believe in a culture of diversity, inclusion, equality, and pride.


The boutique hotel is open 24 hours a day; our restaurant (including coffee bar and beer/wine bar) is open Sunday, Monday, & Tuesday from 8a-3p; Wednesday-Thursday 8a-9p; and Friday-Saturday 8a-10p.

Our History

The Reserve Retreat is a unique property: a boutique hotel with cozy guest rooms; a restaurant serving American fare; a beer/wine bar; a coffee shop; a venue for live music; and space 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 Charles and Edith Ringling (of circus fame). The homes were used until sometime in the 1920s when Mr. and Mrs. Ringling built their grand estate Cad’Zan.

The buildings were moved by a mule team to their location on Tamiami Trail, then a dirt road. The third building was erected and the compound was used a 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 Chris Haas, and Events Manager Sarah Sellers, and courteous staff members all help create a five-star atmosphere for all guests.

The Owner

Jessica Simmons

As founder and owner of The Reserve Retreat, Jessica has more than years of proven experience in building businesses and developing successful and profitable real estate ventures.

Jessica is passionate about helping The Reserve Retreat and other organizations achieve breakthrough results.

As a resident of the North Trail since 1993, Jessica brings her personal and professional experience into developing The Reserve Retreat and making the North Trail a better place to spend time, live, work, and play. She is active on the North Trail Business Partnership and strongly supports a host of community and performing arts organizations.

Jessica Simmons

Recent Honors


Favorite Business



Best Guest Accommodations

Sarasota Herald-Tribune Readers Poll


Best Open Mic Night