Why You Should Plan a Siesta Key Vacation This Fall

Are you looking for a relaxing beach vacation but hoping to avoid crowds and extreme summer heat? Consider vacationing in Siesta Key during the fall. September through November are the perfect months to enjoy a mild temperature while avoiding summer and winter-break crowds. 

Fall Weather

Temperatures average in the 80s (around 30 degrees Celsius) during the months of September and October. In November, the temperature starts to cool, but nothing extreme. Late October and November are ranked as the best time of year to visit Siesta Key climate-wise due to the mild temperatures, pleasant weather, and low rainfall and humidity.

Things to Do

Siesta Beach was rated the #1 ranked beach in the United States and consistently ranked in the top beaches. You’ll have more elbow room in the off-season, so plan to check out this ideal spot in the Fall.

Visit The #1 Beach

Enjoy miles of gorgeous sand and waves while taking advantage of the beach’s public facilities to play volleyball or share a picnic. Get to the beach by catching the Siesta Key Breeze Free Trolley, which operates seven days a week from 10am to 10pm. Snacks and beach toys are also available at the public beach pavilion.

Visit Point of Rocks to the South of Siesta Beach to snorkel or search for shells along the shore. If you’re lucky, you might also catch a glimpse of dolphins and manatees, but even if you don’t, there are plenty of marine wildlife tours that will take you to the very best wildlife hotspots. Kayaking and parasailing are also available. Mote Marine Laboratory and Aquarium, north of Siesta Key on City Island, is worth a visit and provides many educational resources about the wildlife you will encounter. 

Visit Sarasota

St. Armand’s Circle, the cultural center of Sarasota, offers plenty of fresh seafood options, but you can also find international restaurants, such as Venezia Italia Restaurant and Café L’Europe. Besides food, St. Armand’s Circle has many popular chain stores and local boutiques, great for window shopping or finding that perfect souvenir.

Chill in Siesta Key Village

Feel free to walk or bike around the island in the cooler weather, but the heart of the island is located in Siesta Key Village . There are plenty of places to dine, shop, or grab a drink.

For breakfast head to the Sun Garden Café or Another Broken Egg. For a quick treat and coffee stop by the street stall Meany’s Mini Donuts.

For those who enjoy the finer things, enjoy a glass of fine wine and incredible steak at the Summer House restaurant. Keep in mind that all of these places are within walking distance of just about all of our Siesta Key beach rentals.

Plan Your Vacation

Whether you are looking for a townhouse or condo, a rental with a view, or a space that caters to pets, you are sure to find what you’re looking for. Rentals include parking, WiFi, pools, covered patio, entertaining area, and more. All properties are located within easy walking or biking distance from the beach.

Fall Events

October is the perfect time to enjoy fall and Halloween-themed events in and around Siesta Key. The Downtown Sarasota Craft Festival, just a few minutes drive from Siesta Key, is the perfect opportunity for some souvenir shopping while learning more about the local culture. You will find local clothing, handmade soaps, gourmet spices and herb, organic food, paintings and artists from all over the world. And don’t forget to try Sarasota’s famous kettle corn!

Selby’s Spooktacular, the Sarasota Pumpkin Festival, and the Halloween and DIY Night Market are all great way to celebrate Halloween with the family while in Siesta Key. At Selby’s Spooktacular, kids indulge in candy and go trick-or-treating along the spectacular Marie Selby Botanical Gardens. The Sarasota Pumpkin Festival includes live music, carnival rides, and the opportunity to bring your very own pumpkin home. Also enjoy music, crafts, food, and Halloween-inspired events at the Halloween and DIY Night Market. All Halloween events take place at the end of October. 

Luxury Vacation Rentals

With our Siesta Key condo rentals and our neighboring Lido Key vacation rentals, we offer the ideal escapes for you and your loved ones to enjoy a fall vacation. Homes ranging from two-bedroom, three-bedroom, and even five-bedroom plus rentals are available.


Siesta Key Luxury Rental Properties
5111 Ocean Blvd. Suite B, C & D
Siesta Key, Florida USA 34242
Hours of Operation: 9am - 5pm
#SiestaKeyLuxury #iHeartSiestaKey

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