While spring and summer in Siesta Key may get all the attention, locals know the fall months are truly a treat. The crowds are long gone, the temperatures are still warm, and lower rates on lodging make it a perfect time to visit! Pair that with the flexibility of a short stay in one of our Siesta Key vacation rentals, and you’ll see why Siesta Key is ideal for a mid-week or long weekend getaway.
One of the best parts of visiting Siesta Key during the off-season is the flexibility. With fewer crowds and a more relaxed pace, you can plan a trip that works around your schedule and gives you plenty of time to enjoy the coast your way.
The Classic Long Weekend Escape: Short on PTO? A Thursday-to-Sunday vacation is an easy way to enjoy a change of scenery without using much PTO. Make the most of your time by choosing a few things you really want to enjoy, whether that’s spending the afternoon on the beach, grabbing dinner at a waterfront restaurant, or unwinding at your Siesta Key beachfront vacation rental.
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The Midweek Escape: Have a more flexible schedule? A midweek trip is a great way to experience Port Aransas at an even more laid-back pace. Plan a Sunday-to-Wednesday, Monday-to-Thursday, or Tuesday-to-Friday stay and enjoy quieter surroundings, more time to explore, and fewer crowds. It’s also a great option for remote workers, retirees, couples, or anyone who can take advantage of a flexible schedule.
Our Siesta Key vacation rentals offer guests a comfortable setup for a long weekend getaway or mid-week stay. Consider booking one of these properties below:
Bianco Sands - A collection of 9 Siesta Key Beach villas, ranging from 1-bedroom to 3-bedroom. These units are a great option for small families or larger groups who want to spend time together while still enjoying the privacy and comfort of their own accommodations. You're just a minute's walk from Crescent Beach and less than a half mile away from the bustling Crescent Village.
Crescent Beach Villas - Our two Crescent Beach Villas feature 2 bedrooms and 2 baths and comfortably sleep 6 guests. The casitas boast cozy, stylish decor with fully equipped kitchens and updated interiors. Spend your afternoons floating in the pool, or walk to nearby Crescent Village and grab a bite to eat at a Siesta Key favorite - Spearfish Grille!
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Lookout - Book one of our luxury Siesta Key vacation homes and experience the best of the island. With 4 bedrooms and 4 ½ baths, Lookout offers enough space for up to 10 guests. Enjoy coffee on the balcony while taking in beautiful beach and Gulf views, swim laps in the private heated pool, or walk over to Siesta Key village for some of the island’s best shops and restaurants. This home will have you wanting to return year after year.
- Beach - Temperatures during this time of year average in the 70s, and yes, you can even swim in Siesta Key during the fall months! Water temperatures reach the mid-70s in November, making it comfortable enough for a midday dip in the clear blue waters. Spend sunny days soaking up the Floridian sun and lounging on the beach with your favorite book in hand.
Fall’s mild weather and calmer waters also make for excellent fishing in Siesta Key. Top targets include redfish, snook, speckled trout, and Spanish mackerel, and there is less competition from the crowd.
Eco-Tour with Siesta Key Snorkel - Join Siesta Key Snorkel for an unforgettable day on the water. Their guided snorkel excursions take you into the beautiful waters surrounding Siesta Key, where you’ll have the opportunity to experience marine life up close.
- Shopping - Stroll through Siesta Key Village to browse local boutiques, beach shops, souvenir stores, and unique finds, or head to South Village for more shopping and places to grab a bite along the way.
- Siesta Key Fall Events - Fall is bustling with exciting events on and near Siesta Key! In October, expect several Halloween-themed events like the Scarecrow Stroll and Siesta Key Safe Treats. Make the drive to Hunsader Farms in Bradenton for a day of live entertainment, a pumpkin patch, hayrides, pony rides, a petting zoo, and so much more.
In November, one of Siesta Key’s biggest annual events, the Crystal Classics, takes place. 24 talented sand sculptors from around the world put their talent to the test at Siesta Beach. And that’s not all! You can cross the bridge over to Sarasota for the Living Arts Festival, a weeklong celebration of the arts.
Tailor your short-stay vacation in Siesta Key the way you want to, whether for a long weekend or a midweek stay. Our Siesta Key vacation rentals are equipped with everything you need for a relaxing fall escape.
