Our Historic Neighborhood

Gillespie Park, home to the Boat House, Lighthouse and White Cottage, is a historic downtown neighborhood with charming early 20th century cottages and bungalows.

Gillespie Park is named after the first mayor of Sarasota - John Hamilton Gillespie. The Park is located in the center of the neighborhood; this 10-acre area has many trees, a little lake, bicycle & walking paths, a recently renovated children’s playground and a tennis court. Across from the Park is a basketball court. The proud residents, the majority of them having restored their cottages, are very engaged and invest time and energy to make this downtown community a great place to call home.

There is so much to do and see within a few minutes walking distance. You can stroll the Historic Downtown Village with the popular Breakfast House, Tea House, art and gift galleries such as the Artful Giraffe.  Walk a few minutes in the opposite direction and you will find Savory Street Restaurant, Pomona Bistro and Wine Bar, Blue Rooster restaurant (great venue for live music).  Last, but not least, a few minutes walk to Main Street in Downtown Sarasota, you will find a movie theater, and endless fine restaurants, galleries and eclectic shops.

This very lively walk-to-downtown neighborhood is a joy to live in and a joy to many who visit.  Don't feel like walking? Sarasota's iRide offers free transportation on-demand to anywhere in the downtown area, which includes pick-up and drop-off at the front door of all our homes.  Ask us for details when you check in.

In just a short 5-10 minute drive, you can be on the Florida Keys, home to some of the best beaches in the world.  You are sure to find something for every family member in close proximity to our homes.  

If you are looking for a particular activity nearby, ask us.  We are happy to help make your stay memorable and fun.

Local Event Schedule

Most events are within 10 minutes of our properties, many within walking distance.  Hope to see you there!
  • Oct 7 - 15 minutes from Yoga in the Park. from 9:00 a.m. -10:00 a.m. FREE yoga class in the park at Nathan Benderson Park. There will also be a live DJ and yoga will be led by two Yoga Shack instructors.
  • Oct - 2.9 miles from the The Night Market at Siesta Key. Welcome Fall, check out The Night Market at Siesta Key. Every Friday in October 5:30 p.m. -9:00 p.m. The Night Market offers a trendy, chic multi-vendor shopping experience in a unique night market setting at Westfield Siesta Key. More than just a place to shop, it’s a visual and eclectic experience offering local makers a platform to show off their rare designs & finds.

Just Steps Away from Everything

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