Siesta Key Things to Do and Area Info

Siesta Key, Florida, is one of the most exciting and picturesque places to vacation on the coastline of the Sunshine State. There’s a little something for everyone here, whether you’re looking to go shopping, dine on local cuisine, explore the area’s history, check out wildlife, and so much more. Are you visiting Siesta Key for the first time? Want to know some of the activities you can’t miss while here? Here’s a quick guide to the best Siesta Key things to do and area info to get you started. Book your Siesta Key vacation rental and get to planning!

Siesta Key Village

Siesta Key Village is easily one of the most popular attractions in this area, and there’s no question why. Visitors and locals alike flock here to experience the abundance of shopping, dining, and entertainment opportunities throughout the year. All in all, you’ll find around 100 retailers to visit! The shops and restaurants are open all year long, and there are also fun festivals that take place periodically throughout the year, including the famous Siesta Fiesta. There’s plenty of parking here, too, so you can park here and stroll down to the multiple beach access points nearby. No trip to the island is truly complete unless you’ve spent an afternoon at Siesta Key Village!


Siesta Key Village is great for shopping, but it’s not the only place where you can find something new for your wardrobe or grab a unique souvenir. Islander Trader Boutique is an island staple, offering one-of-a-kind items that will help you remember your travels. Gidget’s Coastal Provisions is another excellent option, offering all kinds of clothing, books, soaps, and more.

Are you looking for something even more unique? Pick out a custom painting inspired by the island when you visit The Gallery on Siesta Key. Grab your beach essentials at Beach Bazaar, find a new piece of apparel at Siesta Key Outfitters, or get active at CaliFlorida Surf and Skate Shop. No matter what you’re looking for, you can find it on Siesta Key!


Are you interested in checking out the local arts community? There are tons of great places to do just that! We’ve already mentioned The Gallery on Siesta Key and Gidget’s Coastal Provisions, but you can also purchase breathtaking artwork at the Siesta Key Farmers’ Market and Captain Curt’s Gift Shop. Talented local artists such as Shawn McLoughlin and Ryan Gamma often have their work on display and sale at these locations. 

If you want to get involved in the arts world, don’t miss a chance to participate in the Siesta Key Drum Circle. Here, locals and visitors come together to make music, dance, and have fun as the sun sets over the waves. You can either sit back and enjoy the performances or join in with your singing, dancing, and musical stylings!


With so many fun things to do in this area, you’ll need a convenient and affordable way to get around. It can be a hassle to drive or walk from place to place, so you might want to opt for the trolley instead. The Siesta Key Breeze Trolley is always free and operates seven days a week, making journeys from Ocean Boulevard down to Beach Road and onto Midnight Pass Road. You can find trolley stops near Siesta Key Village and on Stickney Point Road. To make your travels even more manageable, download the Trolley app on your phone to track where the trolley is and when it will arrive at your stop! 

Downtown Sarasota

Just because you’re vacationing in Siesta Key doesn’t mean you’re limited to what’s on the island itself. You can easily make a trip to downtown Sarasota for even more to see and do! Experience the breathtaking nature on display at the Marie Selby Botanical Gardens, get up close and personal with marine life at the Mote Marine Laboratory and Aquarium, or head to the Ringling to see circus exhibits, stunning artwork, beautiful gardens, and so much more. Downtown Sarasota is also home to shopping and dining opportunities to suit every taste, so there’s no question you’re in for a great time!

There are countless destinations and activities you can experience during your stay on Siesta Key, but there’s no way to accomplish them all in one day! To make the most of your time here, you’ll want to find a convenient and comfortable place to stay. That’s where we come in! We are proud to offer a wide range of rental homes and condos for your group to enjoy. Contact us today to learn more and to book your trip!


Home & Condo Rentals and
Property Management Inc.
6623 Midnight Pass Road
Siesta Key, FL 34242
Local: Call OR Text 941-349-8100
Toll Free: 1-888-607-5181


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