When you look at the calendar and realize that winter and its frosty days and frozen nights are zooming your way like a runaway train and wish desperately you had a way to derail it, we at Rent Siesta Key have the perfect solution to a seemingly unsolvable problem! Obviously, a winter getaway to a place where summer blooms eternal and the only frozen things are the frosty margaritas you will be sipping as you watch the sun fall spectacularly into the sea! Offering warm days, slightly cooler nights, and because you chose our seasonal sanctuaries for your vacation accommodations, all the comforts of home, your Siesta Key vacation will be one that rescues you from the cold and creates the happiest of memories! This guide to helping you fill those winter days with fun and frolic will ensure that this trip will be the best trip you have ever taken!

Siesta Beach Seafood & Music Festival, December 1st – 3rd 

With highs in the 70s of course our summer loving guests will want to spend as much time at the beach as possible and the Siesta Beach Seafood & Music Festival offers another fun way to do so! In case you weren’t able to tell by the title of the event, this 3 day long festival promises to provide all the music you love to dance to, all the sweet seafood you will want to devour, and vendor booths selling locally created art, crafts, and foods, ensuring you can get a jump start on your holiday shopping! 

47th Annual Sandy Claws Beach Run, December 9th, Siesta Beach 

For nearly 50 years Siesta Beach has been the site of the Sandy Claws Beach Run, offering both a 5K and a 1-mile fun run for all interested participants. Proceeds go to the Summer in the Parks Adopt-A-Camper, so you can be sure that your $20 (for the 1-mile fun run/walk) $25 (for the 5K Youth Run, 17 & under) or $35 (for the 5K adult run) is a worthy investment. Providing a finisher medal to all who participate, awards for winners in every age group, music, food, and raffle prizes, as well as a holiday themed costume contest, event tees will also be given on a first come first serve basis until supplies run out! 

Stock Your Rent Siesta Key Kitchen with Goodies from the Farmers Market 

Our fully equipped Rent Siesta Key kitchens come with everything you need to prepare a meal, except for the food, and a visit to the Siesta Key Farmers Market (5104 Ocean Boulevard) can be the most fun way to stock your shelves! Unlike the Farmers Markets in your wintry hometown, ours stays open year-round, selling farm fresh produce, homemade baked goods, and a variety of products that will make wonderful souvenirs or gifts! Open Sundays 8-noon. 

Rainy Day Activities 

Although it doesn’t rain as much in the winter months as it does during the rest of the year, there may be at least one rainy day during your winter getaway and if a little sky water makes you melt, these rainy day activities will keep you dry! The Sarasota Classic Car Museum, 5500 N Tamiami Trail offers 60,000 square feet of classic vehicles of all types, including Bentley’s, Alfa Romeros, Cadillacs, and a beautifully restored “horseless carriage” from the beginning days of automobiles.  

While you are in Sarasota, a visit to the Ringling is a must do, offering a museum of everything circus, circus-related art, and a chance to see how the ultimate circus man, John Ringling, lived out the remainder of his days. The Mote Marine Laboratory and Aquarium, also located in Sarasota will provide a comprehensive look into the sea and the creatures that make the waters their home, providing a fascinating activity on a rainy day in Florida. 

Beach Bars for the Win 

To celebrate warm days in the middle of winter, a visit to any of the local beach bars will enhance your vacation escape, starting with the Siesta Key Oyster Bar (SKOB) located at 5238 Ocean Boulevard. Offering live music, delicious food, and all the tropical drinks you can drink, we suggest trying the Grouper Sandwich with a Rum Runner for a typical Florida feast. The Daquiri Deck, formerly Café Gardens, has been a local staple for more years than we can remember, offers a Lobster Roll on its menu, live music that plays late into the night, and a legendary happy hour that will be the perfect start to a night of Florida fun! 

Rent Siesta Key 

When it’s time for your more thrilling adventures to end and the comfortable ones to begin, our Rent Siesta Key seasonal sanctuaries step up to welcome you home as they pamper and spoil! Reserve your favorite escape and contact us today!