Welcome to Gulf & Bay Club Bayside, where every stay delivers comfort, character, and connection. Unlike hotels that rely on a star rating system, our Siesta Key vacation rentals provide something truly unique; personalized experiences shaped by each home’s style, location, and owner.
Staying in a Siesta Key vacation home offers more than just extra space, it offers a better way to travel. Enjoy spacious living areas, multiple bedrooms, fully equipped kitchens, and private outdoor spaces ideal for relaxing after a day on the beach. Many guests also find that vacation rentals provide exceptional value compared to traditional hotels, especially for families or extended stays.
Each Gulf & Bay Club Bayside rental reflects the laid-back luxury and charm that define Siesta Key. From coastal-inspired décor to inviting outdoor lanais, every home tells its own story. These are not just rental properties, they are welcoming spaces where owners have created environments designed for connection, relaxation, and unforgettable memories.
The uniqueness of our homes is what makes Siesta Key vacation rentals so special, and maintaining that individuality while ensuring quality is at the heart of what we do. Our professional property management team follows strict cleanliness and maintenance standards to ensure every guest enjoys a safe, comfortable, and worry-free stay.
When you stay at Gulf & Bay Club Bayside, you’re not just booking a place to stay, you’re discovering what makes Siesta Key one of Florida’s most beloved destinations. Beautiful beaches, a welcoming community, and thoughtfully managed vacation homes come together to create an experience that feels authentically coastal and uniquely yours.
At Gulf & Bay Club Bayside, we believe in controlling what we can to ensure your stay is seamless, comfortable, and memorable. From cleanliness to amenities, every aspect of our Siesta Key vacation rentals is designed to exceed expectations.
At Gulf & Bay Club Bayside, we believe in controlling what we can to ensure your stay is seamless, comfortable, and memorable. From cleanliness to amenities, every aspect of our Siesta Key vacation rentals is designed to exceed expectations.
We provide honest, up-to-date photos and descriptions that reflect the true condition of each property. Occasionally, homeowners may make small updates, replacing furniture, upgrading equipment, or remodeling rooms. These improvements may slightly alter the appearance of the home but are always intended to enhance your experience.
Our Guest Services team is available 24/7, 365 days a year. No exceptions. Whether you have questions before your arrival or need assistance during your stay, we’re here to ensure your visit to Siesta Key is smooth and enjoyable.
Every Siesta Key vacation rental we manage meets a high standard of functionality and comfort. Many homeowners go above and beyond, adding personal touches and extra amenities so you can truly feel at home while on vacation.
Occasionally, equipment may need repair or replacement. If a maintenance issue arises, we act quickly to resolve it. Unlike hotels, vacation homes may have unique layouts or private utilities, so some repairs may take longer. Utility outages or service interruptions are outside our control, but we always work to minimize any impact on your stay.
