Why Siesta Key is the Best Winter Destination for You

If you’re looking for somewhere to experience all the fun and sun of a Florida vacation without the huge crowds, Siesta Key is the place for you.

This family-friendly vacation destination is perfect all year long, but experiencing Siesta Key in the off-season will give you a special chance to spend time with your loved ones in this sunny winter paradise. Siesta Key is located near some amazing day trips, and there are plenty of fun holiday events to participate in.

Here is your full guide to spending winter in one of the best Siesta Key Beach resorts.


Siesta Key weather in the winter is cool enough so that you’re not miserable but still warm enough for you to take a dip in the water. In the months of December, January, and February, high temperatures range from the low-to-mid 70s, while lows stay in the low-to-mid 50s. You can still come out to the pool during the day and just throw on a light jacket in the evening to keep exploring. Winter is also the dry season in Siesta Key, so there is little chance of you running into a storm.

Things to Do

There are tons of fun attractions right near our Siesta Key hotel and vacation rentals. During the warmer parts of the day, you can venture off on a kayak tour or splash around at Crescent Beach. The nearby Marie Selby Botanical Gardens are the perfect place to spot some gorgeous flora, and there are plenty of indoor attractions as well for the cooler days, like the Ringling Art Museum or Livingston’s Amusement Center.

About Downtown Sarasota

It’s only a 15-minute drive from Siesta Key to downtown Sarasota, where you’ll find plenty more attractions and fun in the sun. 

Make sure to visit Main Street for some incredible shopping, and take the kids to run around at JD Hamel Park. Art Uptown is great for getting some culture, and the whole family will love interacting with the sea life at the Mote Marine Laboratory & Aquarium. The Center for Architecture is another unique destination that the whole family will enjoy. 

Winter Events

In addition to all of these attractions, the Siesta Key area has plenty of special winter events for you to enjoy. If you want to get into exercise on your vacation, sign up for the Sarasota Christmas Glow 5K Run. You will start at Nathan Benderson Park in all of your glow gear and run around the beautiful city of Sarasota. When you’re finished, you’ll get cocoa and other snacks as a reward!

Of course, you want to visit Santa while you’re in town, and the Powel Crosley Estate is the perfect place to give Old Saint Nick your Christmas list. Come out to enjoy An Evening with Santa Clause, where you will hear stories, play games, and enjoy a festive lunch, snacks, and a hot cocoa bar. This event will be happening on December 17th and December 23rd from 11 a.m. until 3 p.m. both days.

Where to Eat

There is so much good food in and around Siesta Key, you can try a different cuisine for each meal! Selva is popular for its delicious Peruvian dishes, while the Siesta Key Oyster Bar is perfect for seafood lovers. Boca Sarasota has a delicious farm-to-table emphasis, or you can head to Snook Haven for a relaxed dinner. Don’t forget to finish your meal with a cold treat from Big Olaf Creamery or a coffee from Meaney’s Mini Donuts & Coffee House.

Places to Stay

All of these restaurants, attractions, and events are conveniently located near our Siesta Key rentals, so you can get out the door in a hurry and can easily return to your home at the end of the day. We have rentals for all sizes of parties, and we even haveĀ Siesta Key pet friendly rentals so Fido can come along too! For more information on planning an unforgettable Siesta Key vacation in the winter, contact us today!

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