Gertrude Rentals Blog

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....

Celebrate the Holidays in Siesta Key, Florida Dreaming of a white Christmas made of sand instead of snow? Siesta Key, Florida, transforms into a tropical winter wonderland each holiday season. With twinkling lights, beachside events, and plenty of Santa sightings, this island offers the perfect mix of festive cheer and coastal charm. Whether you’re staying for a weekend getaway or an extended holiday vacation, here are the top Christmas events...

Dreaming of Siesta Key’s white sand and turquoise waters? The good news: getting here doesn’t have to break the bank. With a few smart strategies, you can score affordable flights to Sarasota–Bradenton International Airport (SRQ) — the closest airport to Siesta Key, just 20 minutes away. Whether you’re planning a quick beach escape or a long vacation, here’s a step-by-step guide on how to save money on airline tickets to...

When it comes to planning the ultimate girls’ getaway, Siesta Key, Florida, checks every box. With its world-famous white quartz sand, turquoise waters, and vibrant island vibe, Siesta Key is the perfect backdrop for making unforgettable memories with your best friends. Whether you’re celebrating a birthday, a bachelorette weekend, or just need some quality time together, this Gulf Coast paradise offers the perfect mix of relaxation and adventure. Beach Bliss...

The Ultimate 3-Day Itinerary for Siesta Key First-Time Visitors What to See, Eat, and Explore on Your First Beach Getaway? Siesta Key, Florida, is a slice of paradise on the Gulf Coast known for its powdery white sand, warm turquoise waters, and laid-back beach town charm. Whether you’re planning a relaxing retreat or a fun-filled adventure, this 3-day itinerary is perfect for first-time visitors looking to make the most of...

Welcome to Siesta Key, where tropical charm meets culinary excellence. Whether you’re craving fresh seafood, authentic global flavors, or a laid-back pub bite, Siesta Key Village has a table waiting for you. Here’s your go-to guide for Gertrude’s favorite dinner, dessert and breakfast spots spots on the island:   Dinner Dining Guide: Siesta Key Village The Cottage A cozy and upscale gem offering a modern American menu with a seafood...

Top Attractions of Siesta Key: A Beach Lover’s Paradise Siesta Key offers an irresistible mix of sun, sea, and outdoor adventure, making it one of Florida’s most beloved beach destinations. From bustling public beaches to secluded coastal gems, here are the top beach attractions that draw visitors year-round: Siesta Public Beach Why It’s Popular: Siesta Public Beach is the island’s largest and most iconic beach. Famous for its soft, cool-to-the-touch...

Siesta Key isn’t just a beautiful place to catch some sun—it’s a true family vacation paradise. With powdery white sand, calm Gulf waters, and a welcoming, laid-back vibe, it’s a destination where parents can unwind and kids can create lifelong memories. From outdoor adventures to marine life encounters, this guide covers everything you need to plan an unforgettable family trip to Siesta Key. Why Choose Siesta Key for a Family...

How to Save $500 a Week on Siesta Key Going out is fun—and yes, you should absolutely do it—but the real goal of any vacation is to relax, connect, and make memories. Here’s a smart way to do that without draining your wallet. Start & End the Party at the Rental — Save $100+ Per Couple, Per Day Why it works: Bars on Siesta Key are fun, but they’re not...