Gulf & Bay Club Bayside

We offer vacation rentals to guests from all over the world! We have a very exquisite property with the nicest marina on Siesta Key. Enjoy beautiful views of the Gulf of Mexico, our pool or tranquil bay views from every unit in the building. Sip your morning coffee out on your own personal screened in lanai or head out to the gazebo overlooking the bay for some bird watching, dolphin spotting and boats strolling by.

We’re a family-loving couple from Connecticut who first fell in love with Siesta Key on our honeymoon. Years later, with five kids, our passion for this magical place has only grown. Inspired by our family experiences and countless cherished memories here, we’ve poured our hearts into creating vacation rentals that feel just like home. We’ve thoughtfully equipped our rentals with all the necessities to ensure a comfortable and hassle-free stay, hoping to make your visit as special as our many trips here have been for us. We look forward to welcoming you and sharing the charm of Siesta Key!

2192, 5858 Midnight Pass Rd

5683 Midnight Pass Rd APT 105

Beachside Management is a premier vacation rental company based in Siesta Key, FL. With over 50 separate vacation rentals that suite 2-4 persons all the way up to large homes directly on the beach that comfortably suite 10 plus persons. Our staff is extremely knowledgeable and courteous and is standing by to help our customers experience the vacation of their dreams. We offer many amenities included in staying with us, such as beach equipment, Keurig coffee makers, complimentary snacks and water, and so much more. Stay at the vacation rental of your dreams and stay with Beachside Management, while staying on Siesta Key!

Siesta Key Sea Club II is the perfect place for your vacation! In a gated complex, besides access to the #1 beach in the USA, there is a perfectly heated swimming pool, unbelievable fishing, a relaxed environment, a beautiful lawn to lounge on by the Intracoastal waterway, boating, parasailing and lots more. Chill out by the Intracoastal and you may see a pod of dolphin swim by, or a manatee and calf! In the evening, head out to the beach to see the sunset or Sunday evenings, catch the Siesta Key drum circle. Looking for more to do – head down to Caspersen beach to find some fossilized shark’s teeth. Rainy day – visit The Ringling museum (free on Mondays). What do you do in the evenings – Siesta Key Nightlife.

Vacation Rental Siesta Key Beach Sea Club 5B

Siesta Key Sea Club II is the perfect place for your vacation! In a gated complex, besides access to the #1 beach in the USA, there is a perfectly heated swimming pool, unbelievable fishing, a relaxed environment, a beautiful lawn to lounge on by the Intracoastal waterway, boating, parasailing and lots more. Chill out by the Intracoastal and you may see a pod of dolphin swim by, or a manatee and calf! In the evening, head out to the beach to see the sunset or Sunday evenings, catch the Siesta Key drum circle. Looking for more to do – head down to Caspersen beach to find some fossilized shark’s teeth. Rainy day – visit The Ringling museum (free on Mondays). What do you do in the evenings – Siesta Key Nightlife.