Halloween by the Sea
Halloween on Friday, October 31, 2025, is shaping up to be one of the best nights of the year in Siesta Key. Between the beautiful fall sunsets and ocean breezes, this island knows how to mix tropical charm with spooky fun. Whether you’re looking for family-friendly trick-or-treating or a beachside costume party, Gertrude Rentals has rounded up the best things to do this Halloween season.
1. Siesta Key Safe Treats
Location: Siesta Key Village – 5200 Ocean Blvd, Sarasota, FL 34242
Time: 3:00 pm – 6:00 pm
This long-running local favorite turns Siesta Key Village into a candy-lover’s paradise. Shops and restaurants deck out their storefronts with cobwebs, pumpkins, and plenty of candy bowls for young trick-or-treaters. Expect live music, costumes galore, and that perfect mix of small-town charm and island sunshine.
A family enjoys Siesta Key Safe Treats in full superhero style, showing off their coordinated Incredibles costumes during the island’s beloved Halloween tradition.
Travel Tip: Arrive early to find parking or rent bikes to cruise into the Village. Don’t forget your reusable trick-or-treat bags — the merchants are generous!
2. Big Tiki Halloween Party & Costume Contest
Location: Big Tiki Lounge, 5311 Ocean Blvd, Siesta Key FL 34242
Time: 6:00 pm – 10:00 pm
Once the kids’ candy haul is complete, grown-ups can head to the Big Tiki Lounge for a night of fun under the palms. The party features live island-rock bands, signature tiki cocktails, and an annual costume contest with prizes for the best individual and group looks.
Live music and tropical nights. The perfect combination. Cheers!
Costume Idea: Tropical zombies or beach-bum vampires — island style!
3. The Beach Club Siesta Key – Halloween 2025 Party
Location: 5151 Ocean Blvd, Siesta Key, FL 34242
Time: 8:00 pm till late
For those who prefer flashing lights and pulsing beats, The Beach Club hosts one of the biggest Halloween parties on the island. Expect DJs, laser shows, themed cocktails, and some of the most creative costumes you’ll see all year.
Dance floor status: LOCKED IN. The Beach Club never disappoints!
Travel Tip: This event draws a crowd — use a rideshare or plan ahead for parking. Guests staying with Gertrude Rentals near Ocean Blvd can easily walk!
4. Siesta Key Scarecrow Stroll (All October)
Location: Throughout Siesta Key Village
Dates: October 1 – 31, 2025
All month long, Siesta Key businesses get creative for the Scarecrow Stroll. Walk through the Village to admire dozens of handmade scarecrow displays — from beach-themed pirates to spooky mermaids. It’s a fun and free way to explore local shops and grab ice cream or coffee while you’re at it.
Mermaid life during the spooky season. The Siesta Key Scarecrow Stroll is officially underway!
Fun Idea for Guests: Post your favorite scarecrow on Instagram and tag #GertrudeRentals for a chance to be featured on our social pages!
5. Spooky Fun Beyond Siesta Key
Looking to explore a bit beyond the island? Here are a few Halloween experiences just a short drive away:
Sarasota Ghost Tours – Evening walking tours through historic Sarasota, filled with eerie tales and local legends.
Selby Gardens “Spooktacular” – A family-friendly event at Marie Selby Botanical Gardens featuring crafts, costumes, and light displays.
Bradenton Zombie Pub Crawl – A lively (and undead) bar-hopping experience for adults 21+.
Photo caption suggestion: “More Halloween magic just minutes away from Siesta Key!”
Plan Your Spooky Getaway with Gertrude Rentals
Halloween is one of the most fun times to visit Siesta Key — the weather is gorgeous, the beaches are quieter, and the community spirit is high. Whether you’re looking for a beachfront condo for two or a family home near the Village, Gertrude Rentals has you covered.
Book your Halloween 2025 stay today:
www.GertrudeRentals.com
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