Gertrude Rentals Blog

Owning a vacation rental in Siesta Key sounds simple enough. List it, welcome guests, collect income — done, right? Not quite. Between seasonal pricing swings, guest expectations, local regulations, and constant maintenance, running a successful rental takes strategy. That’s where local Siesta Key property management makes a real difference. If you want your property to earn more — without becoming your second full-time job — here’s why working with a...

If you’re searching for Siesta Key Crystal Classic lodging, you’re not alone. The annual Siesta Key Crystal Classic draws thousands of visitors to Siesta Key Beach every November, making accommodations one of the first things to fill up. This guide covers the best areas to stay, why vacation rentals are ideal during the event, and how to secure the right lodging before peak demand hits. Why Booking Early for Siesta...

Vermont is one of those places that feels quietly special the moment you arrive. Known for its rolling Green Mountains, charming small towns, covered bridges, and strong farm-to-table culture, the state offers year-round experiences that blend outdoor adventure with cozy New England charm. Whether you’re visiting for fall foliage, winter skiing, or summer hiking, Vermont delivers something memorable in every season. Explore the Green Mountains The Green Mountains run the...

Biking on Siesta Key Florida is one of the best ways to experience the island’s relaxed coastal lifestyle. With flat roads, paved bike paths, and ocean views around nearly every turn, cycling is both easy and enjoyable for visitors of all ages. Whether you’re visiting for a long weekend or settling in for a full beach vacation, hopping on a bike lets you explore Siesta Key at a slower, more...

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...