Take A Siesta Key

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Take A Siesta Key Plan your stay, find hidden gems, and experience more

Your guide to the best of Siesta Key 🌴 Discover beaches, restaurants, things to do, local tips, events, and vacation inspiration — plus explore our featured Siesta Key vacation rentals and properties.

10/22/2026

🍂 Fall on Siesta Key might just be our favorite season! 🌴☀️

While everyone up north is watching the leaves change, we’re still enjoying sunshine, beautiful beaches, and sunsets over the Gulf.

The crowds have thinned, the evenings are a little cooler, and the island has that laid-back feeling we all love.

And here’s a little secret… fall can be a great time to find a vacation rental at a better rate than peak season!

🏖️ Have you ever visited Siesta Key in the fall, or do you usually come during another season?

If you could bring back ONE place from the old Siesta Key, what would it be? 🌴 We have a feeling some longtime favorites...
10/21/2026

If you could bring back ONE place from the old Siesta Key, what would it be? 🌴 We have a feeling some longtime favorites are about to come up!

⚾💙💛 RAYS UP! WORLD SERIES BOUND! 🏆What a win for Tampa Bay! The Rays are your American League Champions! 🎉From Tampa Bay...
10/20/2026

⚾💙💛 RAYS UP! WORLD SERIES BOUND! 🏆

What a win for Tampa Bay! The Rays are your American League Champions! 🎉

From Tampa Bay to the sugar-white sands of Siesta Key, we’re celebrating this incredible Florida baseball moment! 🌴☀️

Who’s cheering on the Rays as they head to the World Series? Drop a 💙💛 below!

🌴 Who remembers the ORIGINAL Summerhouse on Midnight Pass Road?The tropical setting, glass walls, and evenings at the up...
10/19/2026

🌴 Who remembers the ORIGINAL Summerhouse on Midnight Pass Road?

The tropical setting, glass walls, and evenings at the upstairs Tree-Top Lounge… such a memorable piece of Siesta Key history. ✨

Did you go there for dinner, dancing, or a special occasion?

📸 We’d love to see your old Summerhouse photos! Share your own pictures and favorite memories in the comments.

🌴 Don’t wait for everyone’s calendars to line up.Siesta Key on your own means beach walks at your pace, dinner wherever ...
10/17/2026

🌴 Don’t wait for everyone’s calendars to line up.

Siesta Key on your own means beach walks at your pace, dinner wherever you like, and sunsets worth putting your phone down for.

Our new solo travel guide shares things to do, practical tips, and ways to enjoy a little time for yourself. ☀️

Find it under **Travel Tips & Guides** through the website link on our page.

**Would you take a beach vacation solo?**

10/15/2026

🎃 Fall plans hit differently when they come with beach sunsets! 🌴

Pumpkin festivals, spooky garden lights, trick-or-treating, markets, and Sunday drum circles—October has plenty to explore around Siesta Key and Sarasota.

👉 Find our Monthly Events page through the website link on our Facebook home page.

Which one’s going on your calendar? 👻☀️

10/14/2026

🌴 Your Siesta Key plans could look like this…

A morning on the beach, an afternoon on the water, and dinner with a Gulf breeze. 🌊🍹

Find inspiration on our Things to Do page—visit the website link on our page to start exploring!

What’s first on your vacation list: 🏖️ beach, 🛶 adventure, or 🍽️ dining?

Planning a Siesta Key getaway? Before you hit “book,” read our quick guide: 7 Things to Check Before Booking a Siesta Ke...
10/11/2026

Planning a Siesta Key getaway? Before you hit “book,” read our quick guide: 7 Things to Check Before Booking a Siesta Key Vacation Rental. Learn which beach access points matter, what amenities to confirm, and little details that make a big difference in your stay. Read this guide and others via the link to our Vacation Planning Guides on our home page!

10/10/2026

Your next “I needed this” moment starts on Siesta Key. 🌴🌊

Gulf views, beautiful vacation rentals, and local favorites worth exploring—we’ll help you plan your escape.

✨ Stay • Play • Unwind

Find rentals and vacation guides through the website link on our page.

Who would you bring? ☀️

🐚 Have you explored Siesta Key’s rocky side?Point of Rocks is a favorite for snorkeling, shell hunting, and exploring be...
10/10/2026

🐚 Have you explored Siesta Key’s rocky side?

Point of Rocks is a favorite for snorkeling, shell hunting, and exploring beyond the white sand! 🤿🌊

Our NEW blog shares beach access tips, what to bring, and what to know before you go.

👉 Head to our Take a Siesta Key Facebook home page and look for our Vacation Planning Guides link to find the guide!

Have a Point of Rocks photo or favorite memory? Share it below! 📸

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