The seasons are always changing, but do you want to know what never changes? The comfort, luxury, and style that can be found in our RentTheKeys seasonal sanctuaries! Offering a large portion of the Siesta Key lifestyle with a heaping side of comfort, your vacation promises to be even better than you dreamed it could be! Although there is not much of a change from season to season, your summer will be brighter when you choose to spend it on Siesta Key, and your fall will be more colorful when you choose to visit the area during fall break! This ULTIMATE guide to Siesta Key in the summer and fall is easy to follow and designed to give you the getaway you deserve after working so hard during all the other seasons of the year.

Joyfully Yours

The best moments of your Florida vacation will be spent inside our comfortable homes and condos as you and your family, friends, or traveling companions discover that a rental property can be just as joyful as a person! Today, we are specifically talking about Siesta Key rentals, but rest assured, we have properties all over the region, including Cape Coral, Bradenton, and Anna Maria Island, just to name a few! Offering luxury, comfort, and a joyfulness that will make you smile from your first moments inside until you give it one last wistful glance over your shoulder as you walk slowly to the transportation taking you back to real life.

But it is the beginning we are about to discuss, those first few moments when you realize that this space is going to be yours, joyfully yours over the next week of your life, and as the door swings open, your heart begins to beat faster! Drop your bags where you stand and make your way to the fully equipped kitchen of your dreams; some “journeys” will be longer than others, as you have your choice of condo and home sizes ranging from cozy 1-bedroom condos on the water to spacious 4-bedroom homes that will make you feel at home immediately. This is the room where meals will be made, drinks will be sipped, and stories will be told as you share leftover desserts and secrets and dreams with your favorite traveling partners by the light of the microwave. Updated appliances, custom cabinets, and a cheerful ambience bring back the joy of cooking, even if you choose to spend more time whipping up margaritas than tossing together a meal! Dining rooms with large tables serve multiple purposes, as you and your traveling party play board games together, spend time in conversation, and when you absolutely are forced to, use the space as a temporary work station; high-speed internet ensures a practically glitch-free Zoom meeting, letting you get back to the most important part of all vacations with ease and speed!

Living rooms with soft sofas and chairs are where naps will be taken, books will be read, daydreams will take place, and if you find some time in between all of those activities, television shows will be watched! Our state-of-the-art televisions will make you feel as if you are a part of the action and can also be found in the bedrooms, allowing guests to wind down with their favorite late-night show before drifting off into dreamland. These rooms are our favorites, offering a peaceful space to retreat to at the end of every day. Shut the door and enjoy some much-needed time to yourself, and after a deep and restful night’s sleep, you will awaken ready to face a new day of Florida adventures!

Many of those adventures will take place with in the confines of your Siesta Key seasonal escape as you practice cannonballs in private or community pools, soak tired and achy muscles in hot tubs outside or deep soaking tubs inside, or prepare a feast worthy of royalty in outdoor kitchens. Our homes are designed to be an integral part of your vacation experience and every minute of every day will be that much better because you spent it with us!

A Siesta Key Summer

After exploring the wonders of your Siesta Key escape, the very next thing on your list of things to do is more than likely to hit the beach! The beaches of Siesta Key (and yes, there are three on this relatively small key) have been written about as some of the most beautiful beaches in the world, and it is the sand that holds a huge part of their appeal. Mostly composed of quartz, the granules are fine and pure white, giving the beach an appearance of a snow-covered landscape without all that cold! Framing crystal clear waters that are warm and inviting, the contrast of white sand, turquoise waters, and the cheerful blue skies above gives your beach adventures a crayon box full of color and that is before you start to play!

Now, before we start the discussion of your beach time, you may find your swimwear selection slightly lacking. People who do not live at the beach full time do not realize that we take our swimwear seriously here, and at various times during the week we may have up to three suits hanging over the backs of patio furniture, a load of suits in the washer, and a drawer filled with the remaining! We even have work swimsuits, “formal” swimsuits, and swimsuits that will NEVER be dampened by salt or chlorine water, but that is a story for another day! If you find yourself needing more swim accessories (suits, boogie boards, sunscreen, etc.), Beach Bazaar at 5211 Ocean Boulevard has everything you will need for your beachy adventures.

Now, let’s get back to the beach! The three beaches on Siesta Key, Siesta Beach, Crescent Beach, and Turtle Beach, offer three distinctly different experiences, all of which will nicely enhance your Siesta Key summer shenanigans, so be sure to explore them all during your time on Siesta Key. Siesta Beach is the largest and most well known of the three, offering two concession stands, a year-round lifeguard station, and a playground under the shade that makes the perfect respite area for toddlers and tweens who have had a little too much sun! Crescent Beach leads you to a seascape you do not often find in this section of Florida, a rocky beach called Point of Rocks. This is a popular surfing and snorkeling area, so get out your gear and explore the undersea world while you are here! This quiet beach, however, is away from most of the crowds, so if you just want to sunbathe in private without having to worry about being hit by volleyballs, this is where you should go! Our final beach, Turtle Beach, is popular for shell and shark tooth seekers, sports fans, and fishermen and women, offering volleyball and tennis courts, horseshoe pits, a boat launch, and access to Blind Pass Lagoon, where fishing is allowed with licenses, so bring a pole and have the time of your life!

Your summertime adventures, however, may begin and end with the beach, but there is so much more you can do while you are here! Charter a fishing expedition from Siesta Key Fishing Charters and spend a day out on the waters going after the big guys that can include shark, snapper, and groupers or boat to where the dolphins frolic when you take a Dolphin Cruise from Siesta Key Dolphin Tours. Also offering sunset cruises that are romantic and breathtaking, your time on the waters that surround Siesta Key will possibly be even more fun than your time playing in the waters!
Enjoy a dolphin tour on your next vacation to the Florida Keys

Shopping at Siesta Key Village will tempt you with treasures you never knew you needed, and on rainy days you can stay dry and cool in air-conditioned and enclosed trolleys with a tour offered by Discover Sarasota Tours. The Public Art Tour and Sunset City Tours are two of our favorites, but please feel free to choose the tour that interests you most! When hunger pangs strike—and with all the activities you will be participating in, you WILL be hungry often—a stop in Siesta Key Oyster Bar will give you the penultimate key experience: sucking down raw oysters as you sip rum runners and listen to some guy playing on his guitar and singing about flip flops and margaritas! These moments will feed your soul in ways you never knew you needed, and this summer spent with us on Siesta Key will be one you will never forget.

Falling for Fall on Siesta Key

To be honest, there isn’t a lot of difference between the seasons on Siesta Key, but a Siesta Key fall is a bit cooler, and the beaches aren’t as crowded as they can get in the summer and winter. Fall for most people is about back to school, football, and pumpkin spice everything, but people rarely think about traveling for a beach vacation, making your Siesta Key fall escape one that will be filled with fun without the crowds! Beach days are still popular, so plan on spending plenty of time at the beaches we talked about earlier, and fishing charters are even more successful as fall migration happens right off our coast, bringing out the big guys to feed and hopefully end up on your reel. Most charter captains will clean and bag your catch, so all you need to do is grill them up on the barbecues found on the back porches of our seasonal sanctuaries!

When you venture off the key to explore all the wonders that Sarasota has to offer, you may find yourself signing up for a sightseeing cruise aboard the Marina Jack, docked behind the Marina Jack restaurant on Sarasota Bay! And because tours are the perfect way to get to know what interests you while visiting someplace, we are once again suggesting a tour offered by Discover Sarasota Tours! The slightly cooler temperatures make you want to get outside and play, and their Amish Experience Tour allows you to explore the Amish lifestyle with visits to the shops and restaurants found in the community; Alma Sue’s Quilt Shop offers exquisitely crafted colorful quilts that you NEED to make yours, and Der Dutchman Amish Cooking Restaurant will take your taste buds to new levels of taste!
Enjoy breakfast at restaurants like Restaurant Bonjour French Café to start your day right
But before you begin any of the adventures we have been talking about, remember that breakfast is the most important meal of the day, and if you run out of fuel, you will run out of energy and become unable to enjoy anything! With that being said, we suggest you start out at least one day of your stay with a visit to Restaurant Bonjour French Café, located at 5214 Ocean Boulevard. Offering an ever-changing menu of delicious European breakfast options, including croissants, omelets, quiches, and sandwiches created on baguettes—they serve lunch too—the Bonjour French Café can be a good change from all the seafood you will devour during your Siesta Key getaway. We aren’t saying that you will get tired of the fresh and sweet dishes from the sea, but sometimes you just need some good old-fashioned carbs to make your day!

Just Like That

Your season on Siesta Key has come to its natural conclusion, but before you go, we would lie to offer one more unique activity to squeeze into your daily adventures, and this one takes you back on the water and off Siesta Key. Cruisin’ Tikis Sarasota offers water tours aboard a floating tiki hut! Offering sunset fireworks cruises in the summer, this uniquely Sarasota adventure may be the highlight of a trip filled with fun!

However you spend your days at play in the Sunshine State, coming home each night to the comforts found in our RentTheKeys seasonal sanctuaries will be something to which you eagerly look forward. Contact us and reserve your stay today!