A Florida vacation has long been on the bucket lists of travelers from all over the world, but more often than not, it’s the big cities that attract attention, exotic destinations such as Miami with its hip and trendy vibe, Orlando with its theme parks that kids have dreamed about their entire lives, and Key West, where famous authors once lived and life moves at a slower pace. And then there is one of our favorite of the Florida Keys, the one where sandy beaches are a brilliant white and sunsets are celebrated on Sundays with drum circles and dancing, where the Rum Runners taste better when enjoyed on patios of beach bars overlooking the Gulf. We are, of course, talking about our own island home of Siesta Key, perhaps a Key that you may not have heard of, but that changes today with this list of 10 reasons why you should pick us for your upcoming Siesta Keys vacation, as well as choosing RentTheKeys for your vacation sanctuary.

Fun for the Kids

A family vacation doesn’t always provide fun adventures for children and adults alike, but on Siesta Key, you will enjoy a vacation that will be filled with fun for everyone, from the youngest to the oldest. We will discuss the beaches of Siesta Key later on down this page, as of course, they are at the top of the list of family friendly activities, but first let’s talk about one of the area’s more unique offerings. On a rainy day, a visit to Jumpin’ Fun Inflata Park offers a colorful and energy-filled way of getting your kiddos to play happily together. The park offers 15,000 square feet of inflatable fun as well as the Air Rider Zip Coaster, something that the parents will have a blast trying out as well. Located at 7321 Trade Park in Sarasota, (just a few minutes down the road from Siesta Key) this park will change the way you look at parks forever.

Romantic for Couples

Honeymooners of all ages will fall in love with love as they explore the romantic side of Siesta Key, starting with sunset walks on its white sand beaches. The sight of a sky lit up in a kaleidoscope of colors, the sounds of waves crashing against the shore, and the feel of your partner’s hand in yours create a scene of love so romantic, you both know you will never forget this moment. Enjoy a romantic meal at Siesta Key Summer House Steak & Seafood Restaurant, 149 Avenida Messina, where the seafood is almost as fresh as the words your soulmate whispered in your ear while you were walking on the beach at sunset. A couple’s massage experienced at Spa Experience Siesta Key, 5700 Midnight Pass Road Unit 4b, promises to draw you closer as the most talented hands in the area do away with any muscle tightness or pain.

The Meals You Will Dream About On Your Siesta Keys Vacation

When you look back on your most memorable vacations, chances are the memories that stand out will be not just the incredible sites you visited, but the foods you enjoyed during your journey. For nearly 30 years, the Village Café, located at 5133 Ocean Boulevard, has served the hearty and flavorful breakfasts you just know are going to make your day start out right, offering patio dining and a menu filled with international delights, including Dough-Nutella Fritters! Your lunches at The Cottage, 153 Avenida Messina, will be a treat for your senses and make you feel good about what you are eating, as their Asian inspired seafood-centric menu is created by using local farms and sustainable meats and seafood. And for dinner? The world will be your oyster (which also just happen to be on the menu) at Lobster Pot Restaurant, located at 5157 Ocean Boulevard. Bringing a taste of New England to our thoroughly Southern shores, the Lobster Pot is reasonably priced and totally scrumptious.

Water Adventures

When you are visiting an island surrounded by water, you have to imagine that there will be a LOT of water adventures you can enjoy, and we are happy to tell you that your imagination is correct. Siesta Dolphin Tours offers a variety of Gulf tours, including the opportunity to watch the dolphins frolic in the waters; choose their Sunset Dolphin Cruise for a truly romantic and interesting experience, or if you are a morning person, their Morning Mimosa Cruise is a fantastic option as well. If you are more of a thrill seeker, we suggest you check out the adventures offered by Siesta Key Watersports. Providing adventures that thrill, including jet ski and boat rentals, their parasailing experiences are popular and moderately priced, fitting into most vacation budgets. They also offer dolphin and jet ski tours, so if you try one adventure, you can always return another day and try something new from our list of amazing attractions!

The Circus Is Back in Town

Siesta Key is right off the shores of Sarasota, so many of the adventures you can have may be either on the Key proper or in the town of Sarasota, and as the circuses of our youth are making a reappearance on the national landscape, they have always been a regular part of our existence. Famous ringmaster, John Ringling, and his charming wife, Mabel, settled here in Sarasota, and The Ringling, 5401 Bayshore Road, is a testament to the joy the big man himself brought to our lives. His home, Ca d’ Zan, has been transformed into a museum that provides a peek into their glamourous lifestyle, offering 36,000 square feet of stunning beauty. The Ringling also features a circus museum filled with circus related artifacts, a museum of art, and stunning gardens that will bring peace, joy, and the opportunity to stop and smell the roses to all who visit. Perhaps the most unique part of The Ringling, however, is the Asola Theater, constructed in 1798, and dismantled and shipped to Florida in 1931. Live performances held here provide echoes of its history and the stage with its velvet curtains will take your breath away.

Under the Sea

Another water-related activity that may entice you to visit our white sand shores takes participants on a tour of what lies under the crystal-clear waters you have probably already spent many hours playing in. Snorkeling and scuba diving are two very popular sports, with the first needing very little in terms of equipment or skills. Flippers, mask with snorkel tube, and the ability to swim are all you need to explore Ariel’s world, and if you are unsure about exploring on your own, Siesta Key Snorkel provides 3- and 4-hour tours that will start you on your way to a new obsession. Scuba, however, is a more complex sport, requiring certification, gear that can be quite expensive, and Florida Underwater Sports SRQ, 6920 S Tamiami Trail in Sarasota, provides it all. Offering classes and the help needed to get your certification, they also provide diving trips that will bring you to the best spots to explore the world under the sea. This area of Florida offers quite a few artificial reefs, creating not just great spots to scuba and snorkel but also provide a way of restoring habitats that may have been lost due to development along the coast.

The Sunset

It’s not often people can devote an entire category to the wonder of a sunset, but on Siesta Key, our sunsets are truly worth traveling thousands of miles to experience. We even offer something we call the Siesta Key Drum Circle, taking place on Sunday evenings, starting about an hour before sunset and providing a safe spot to drum, sing, dance, and commune with new friends. This party is a raucous one, and on many occasions, a belly dancer or two may be spotted, sword and fire acts may be present, but the best part is that the drum circle is judgment-free zone, encouraging participants to dance to their own rhythm, to express their joy in whatever way makes them most happy, and to totally live in this perfect and beautiful moment. The noise quiets, however, and the dancing stops when the show we have all been waiting for arrives, the sun dropping into the sea with a flamboyant display of color, fire, and pizazz. Just don’t be surprised when the crowds offer a standing ovation, because this show is definitely Mother Nature’s finest performance.

Festivals Worth Traveling For

Siesta Key and the surrounding towns also offer a variety of festivals throughout the year that will enhance your vacation experience, and although we don’t have the space to list them all, this article is just a brief synopsis of the wonders of Siesta Key, but if you are planning on a November vacation, The Siesta Key Crystal Classic, International Sand Sculpting Festival takes place on November 15-18 in 2024. This event shows off the sand sculpture masterpieces of 24 supremely talented artists from all over the state and the party attached to this fine event is one worth waiting for. Offering sand sculpting lessons, amateur competitions, live music, and a Barefoot Beach Bar Party Tent with free admission and more live music and adult beverages, this fall event is an exciting one that you won’t soon forget. The list of festivals that take place throughout the year is a long one, especially when you take into consideration that Sarasota and Bradenton are near enough to be included in this feast of festivals, so be sure to check our Rent the Keys blogs when planning your vacation, determining which festival may encourage you to make that trip.

The Beaches of Siesta Key

Perhaps the best reason of all to visit is the many beaches of Siesta Key. There are three white sand beaches on Siesta Key—Siesta Beach, Crescent Beach, and Turtle Beach—each offering something unique that makes them stand out in a sea of sand, and the one thing you may notice when you bury your toes in the white sands is just how brilliant white and silky soft our sands are. Created from thousands of years of erosion and travel of Appalachian quartz, this may be the vacation when you truly begin to understand how much sand can make a difference in your vacation adventures. Some of the best family pictures have been taken using the sea oats that grow wild on these beaches as a colorful interruption between sand and sky, and as you play, relax, and explore the beauty of our beaches, you may begin to wish you had discovered Siesta Key a bit earlier in your lifetime.

Our RentTheKeys Florida Escapes

We have come a long way from the days when travelers used to believe that a vacation rental was just someplace to sleep between adventures. Today, we want to be comfortable in our home sweet vacation homes, and we want to be entertained on those days we stick close to home, something that our properties are born to do. Comfortable, luxurious, often offering views of the white sand beaches of Siesta Key, every minute spent with us will be ones you wish could extend out into eternity. Explore all the amenities we offer, private ones in standalone homes, community ones in the condo complexes, relaxing like you haven’t been able to do in so very long and pat yourself on the back for discovering that Siesta Key is one of Florida’s hidden gems you are so lucky to have found. Reserve your favorite escape for a Siesta Keys vacation today!