Gertrude Rentals Blog

Planning a Siesta Key getaway in 2026? Timing your stay around one of the island’s signature events can make your vacation even more memorable. From beachfront fireworks and family-friendly fun runs to world-famous sand sculpting, Siesta Key offers something special nearly every month of the year. At Gertrude Rentals, we love helping guests experience Siesta Key like a local. Here’s your complete guide to the must-see Siesta Key special events...

Siesta Key is world-famous for its powdery white quartz sand and laid-back beach town vibe, but there’s much more to the island than its postcard-perfect shoreline. Beyond the popular spots, locals and repeat visitors know how to uncover a quieter, more authentic side of Siesta Key. If you’re looking to escape the crowds and experience something unique, here are five lesser-known things to do in Siesta Key that showcase its...

Traveling solo doesn’t have to mean feeling alone—especially in a place like Siesta Key. With its welcoming atmosphere, walkable Village, beautiful beaches, and relaxed pace, Siesta Key is an ideal destination for solo travelers looking to unwind, explore, and recharge. Whether you’re planning a peaceful retreat or a flexible, adventure-filled getaway, Siesta Key offers the perfect balance of comfort, safety, and freedom for traveling on your own. A Friendly, Easygoing...

Welcoming the New Year in Siesta Key is a celebration like no other. With warm coastal breezes, festive island energy, and a mix of beachside relaxation and lively nightlife, Siesta Key offers the perfect setting to say goodbye to 2025 and ring in 2026. Whether you’re looking for a laid-back evening by the water or an upbeat night filled with music and dancing, Siesta Key and the surrounding Sarasota area...

Planning a group vacation doesn’t mean leaving your dog behind. A dog-friendly adventure is the perfect way to travel with friends or family who believe pets are part of the experience—not an afterthought. In Siesta Key, sunshine, walkable neighborhoods, and pet-welcoming spaces make it easy to enjoy a stylish, stress-free getaway with your pup by your side. From beachside mornings to relaxed evenings at home, this is group travel done...

A guys’ getaway should feel effortless—no packed schedules, no compromises on comfort, and no stress. Siesta Key, Florida delivers the perfect mix of laid-back beach vibes and upscale living, making it an ideal destination for friends who want to relax, reconnect, and enjoy the good life. Whether it’s a bachelor trip, milestone birthday, or annual escape, Siesta Key offers space, style, and experiences that feel both casual and refined. Why...

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...