What is it about spring that gives us such hope for the future? Is it the promise shown in the budding of trees and flowers? Is it the way spring showers clear the air, turning the sky an unreal shade of blue and making the sun seem even brighter? Or is it something more mundane, perhaps nothing more than the opportunity to travel becoming available because our children get a week off from school? Whatever your reasons for choosing the spring of 2023 to enjoy a fantastic escape to Siesta Key, our vacation escapes at Rent Siesta Key will provide you all the comfort you seek, and this guide to 2023 upcoming spring events on Siesta Key will ensure that every minute of your stay will be filled with fun!

Siesta Key Sunday Drum Circles, Siesta Beach

Starting about an hour before sunset, the Siesta Key Sunday Drum Circles offer an authentic glimpse into life in the Keys. Costing nothing, everyone is invited to this carefree celebration filled with drums (of course!) belly dancers and a sampling of people from every walk of life, including residents of our beautiful state and visitors from all over the world. If you spend your everyday life buttoned up and following all the rules, the drum circle will give you the opportunity to shed your inhibitions and dance like no one is watching!


Siesta Key Oyster Bar Live Entertainment, 5238 Ocean Boulevard

Sometimes the most memorable events are the ones that catch you surprise. An evening out when the music is live, the crowd is friendly, and the vibe is right is one of those memorable moments, especially when enjoyed at the Siesta Key Oyster Bar! Known as SKOB to the locals, the seafood is always fresh, the beverages are always cold, and the music plays live every night of the week, offering up the best of local performers for your entertainment and enjoyment!

Namaste at the Bay, March 23, Sunset Deck at The Bay Park

Yoga and sunsets go hand in hand at this wonderful event that takes us off Siesta Key and brings us to the beauty and serenity found at the Bay Park, 655 N Tamiami Trail. Claudia Baez, owner of Pineapple Studios, hosts this hour long event filled with peace and goodwill, and all you need to participate is a yoga mat, a bottle of water, and a willingness to let go of the negative as you stretch and pay homage to another fantastic Florida sunset!

Laughter at the Players, April 1, 3501 S Tamiami Trail

Laughter is the best medicine and this fundraiser that helps ensure the Players Theater can continue entertaining for years to come will definitely cure whatever ails you. Offering three hours of laughter, three hilarious comedians, and providing gift bags for all ticket holders, this spring fling is destined to be your favorite part of the show! Ticket prices range between $55 and $85 per person and a good time is guaranteed to be had by all who attend this humorous show.

Sarasota Chalk Festival, April 1st through April 4th, Venice Airport Festival Grounds

This next spring event presents a bit of a drive, one that lasts about 40 minutes and will take you through some of the most gorgeous countryside in the state, but we think a visit to the Sarasota Chalk Festival is worth the trip! Featuring the most realistic chalk portraits and giving you the chance to watch the artists complete their masterpieces, there is almost no words to describe the beauty, the realty, and the giggles you will utter when you find yourself trying to stop from “falling in” to a drawing that appears so real but is only chalk!

St. Armand’s Circle Fine Arts Festival, May 27 through May 28

We look at Memorial Day Weekend as the kickoff to summer fun, but we often forget that spring continues for another month, making Memorial Day weekend events an integral part of the spring celebration. St. Armand’s Circle is known for offering boutique stores, haute cuisine restaurants and this amazing Fine Art’s Festival held in the spring. Presenting artwork created by some of Florida’s best artists, spending a couple of hours exploring the exhibits will more than likely help you find that piece of art you have been wanting to hang in your office at home!

Family Barbecues

The family barbecue is a time honored tradition that in your home state is generally only held in the summer months, but spring time on Siesta Key is the perfect time to throw one you will wish never had to end! Most homes offer grills in the backyard, accompanied by pools and/or hot tubs, and we can promise that the fish you caught earlier in the day will taste even sweeter when grilled up by the pool! Reserve your favorite spring sanctuary today! Contact us today!