Gertrude Rentals Blog

Winter might bring snow, ice, and gray skies across much of the country—but on Siesta Key, it brings sunshine, warm breezes, and the most beautiful time of year to hit the beach. From holiday celebrations to perfect weather, here’s why winter is one of the most magical seasons to visit. Perfect Winter Weather While much of the U.S. dips into freezing temperatures, Siesta Key stays comfortably warm.Average winter temps: mid-70s...

Enjoy warm Gulf breezes, white-sand beaches, and a relaxed coastal atmosphere that turns Thanksgiving into a true beachfront escape. Thanksgiving feels different—in the best way—when you celebrate it in Siesta Key. Instead of gray skies and heavy coats, you’ll enjoy sunshine, gentle waves, and powder-soft sand beneath your feet. Whether you’re planning a family gathering, a romantic getaway, or simply craving a break from the cold, Siesta Key offers a...

Every year, the soft white sands of Siesta Beach on Siesta Key are transformed into an awe-inspiring open-air art gallery, and 2025 is no exception. The 15th annual Siesta Key Crystal Classic — held November 14–17, 2025 — invites master sand-sculptors from around the world to turn everyday sand into magnificent masterpieces. For vacation-rental hosts, local businesses, and visitors alike — this festival is a golden opportunity to engage guests,...

If you needed another reason to plan your next getaway to Siesta Key, here it is: Tripadvisor’s 2025 Travelers’ Choice Awards have once again named Siesta Beach the No. 1 Best Beach in the United States — and the No. 4 Beach in the World. It’s official: our slice of paradise isn’t just loved by locals — it’s loved by the world. What Makes Siesta Beach the Best Beach in...

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...