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Siesta Key Vacation Rentals at Gulf & Bay Club Bayside

Welcome To Gulf & Bay Club Bayside, Your Perfect Escape On Siesta Key!

Discover Siesta Key vacation rentals at Gulf & Bay Club Bayside, a gated community located just across from the beautiful white sands of Siesta Key Beach. Our individually owned vacation condos offer a comfortable home base for exploring Siesta Key, with convenient beach access, resort-style amenities and a location close to Siesta Key Village. Choose from one-, two- and three-bedroom vacation rentals, including select condos with water views.

Our vacation rentals feature spacious floor plans, private garages, and in-unit laundry, giving you all the modern conveniences of home within a serene, resort-style environment. Enjoy the beautiful Florida sunshine with access to two heated swimming pools, lighted tennis and pickleball courts, and a well-equipped fitness center. The lush landscapes and gentle waterways surrounding each condo provide a peaceful backdrop, while Siesta Key Village and popular local attractions are just minutes away for shopping, dining, and entertainment.

Experience the privacy and individuality of your own Siesta Key condo, each thoughtfully designed for comfort and style. Stroll to the famous Crescent Beach or catch a sunset at the Gulf, and take advantage of easy transportation options such as golf-cart taxis and the Siesta Key Breeze trolley for effortless island exploration. When you choose Gulf & Bay Club Bayside for your Siesta Key vacation rental, you’re choosing a destination renowned for its friendly welcome, unmatched amenities, and proximity to the best of Siesta Key living.

Start planning your next coastal escape with the trusted team at Gulf & Bay Club Bayside and elevate your Florida vacation in a community that combines serenity, sophistication, and the ultimate Siesta Key experience.

Find Your Siesta Key Vacation Rental

Find the right Siesta Key vacation rental for your next beach getaway. Gulf & Bay Club Bayside offers individually owned one-, two- and three-bedroom condos, along with select rentals featuring water views. Each residence is unique, giving you a choice of layouts, furnishings and amenities while enjoying the same convenient Siesta Key location.

Whether you’re planning a family beach vacation, a getaway for two or a longer stay, explore our available rentals and find the condo that fits your trip.

Siesta Key Vacation Rentals With Comfort and Convenience

Unique Residences, Unmatched Convenience

Individually Owned Siesta Key Condos

Choose from a variety of accommodation sizes among our individually owned condos, each serving as the perfect base for exploring Siesta Key and its surrounding wonders. Convenience is paramount, with each guest rental featuring its own private garage and in-unit washer and dryer.

A Relaxing Siesta Key Location

Experience a unique sense of privacy and individuality in the layout of our units, creating a personalized retreat during your stay. Beyond the comfort of your residence, the stunning Siesta Key and Crescent Beach beckon just across the street, with Siesta Key Village a short stroll away.

Easy Access to Siesta Key Attractions

Getting around is a breeze on Siesta Key. Golf-cart taxis and the Siesta Key tram are readily available, allowing you to park your car, unwind, and forget your troubles. Revel in the best that Siesta Key, Florida, has to offer with ease and convenience.

Why Stay at Gulf & Bay Club Bayside?

A Short Walk to Siesta Key Beach

Gulf & Bay Club Bayside offers deeded walking access to Siesta Key Beach. From the front of the community, the walk to the sand is approximately one-quarter mile and typically takes 7–10 minutes. Guests use a key-fob-controlled pedestrian entrance and follow the community pathway to the beach gate. Beach access is private for Gulf & Bay Club Bayside guests, with access extending from the waterline to the tideline. Beach Access Map

Siesta Key Vacation Condos for Every Group

Choose from individually owned one-, two- and three-bedroom Siesta Key vacation rentals, with a variety of layouts, furnishings and views. Each rental provides the comforts of a private condo, while guests also enjoy the amenities and setting of the gated Gulf & Bay Club Bayside community. Every guest rental includes a private garage and an in-unit washer and dryer.

Resort-Style Amenities

Your vacation extends beyond the condo with a selection of amenities throughout the community. Gulf & Bay Club Bayside features two heated swimming pools, lighted tennis courts that can also be used for pickleball, and a fitness center. Guest rentals also include private garages, and the community offers additional outdoor spaces and waterfront areas to enjoy during your stay.

Close to Siesta Key Village

Gulf & Bay Club Bayside is conveniently located near Siesta Key Village, where you’ll find a variety of restaurants, shops and entertainment. When you’re ready to explore more of Siesta Key, the free Route 77 Siesta Islander trolley provides convenient transportation between Siesta Key Village, Siesta Beach, South Village and Turtle Beach.

Where Coastal Charm Meets Modern Comfort

Discover Serenity & Style

Gulf & Bay Club Bayside boasts stylish vacation rentals and residential-style amenities, providing a haven of comfort and relaxation. Immerse yourself in the tropical ambiance as you unwind by our two heated swimming pools, stay active in our fitness center, or engage in friendly matches on our tennis and pickleball courts.

Book Your Siesta Key Vacation Rental Today

Individually Owned Condos

Choose from a variety of accommodation sizes among our individually owned condos, each serving as the perfect base for exploring Siesta Key and its surrounding wonders. Convenience is paramount, with each guest rental featuring its own private garage and in-unit washer and dryer.

Guest Reviews of Our Siesta Key Vacation Rentals

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Our little paradise

We enjoyed our stay as always. We were in this house for the first time in 1993. (Honeymoon) The furnishings have become more modern. We have been to this complex many times. All houses have their own charm. We will always return there.

Werner M.

Fabulous

Everything was clean and well organized. Location convenient to beach, restaurants and shopping. We’d come back again.

Connie D.

Fantastic

Our unit was great and even better than advertised. Plenty of room and adequate amenities. As someone who has spent hours looking for a parking spot, the short WALK to Siesta Key Beach made it the best. We look forward to staying here in the future. Thank you so much.

Ray M.

Gulf & Bay Club Bayside

Give Us A Call At:

941-346-3499
Property Management

Gulf & Bay Club Bayside

Give Us A Call At:

941-346-3499

Free Rental Evaluation

Discover Your Property’s True Potential


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