Siesta Key Beachfront Vacation Rentals


A New Level of Beachfront Vacation Rentals

Make no mistake: all Siesta Key beachfront vacation rentals are not the same. Many are limited and ordinary, while others are inspiring and exhilarating. And when you call the Gulf and Bay Club your temporary “home away from home,” be assured that you’ll enjoy the latter — every single day, and without compromise. It’s a whole new level of amenities, extras and perks that you simply can’t find elsewhere.

Why Settle for a Just a Balcony or a Backyard?

Siesta Key beachfront vacation rentalsOther Siesta Key beachfront rentals offer you a balcony or a backyard. But at Gulf and Bay Club, you’ll be steps away from your PRIVATE 780-foot sandy white beach, where you can relax in peace and tranquility, or have fun with family and the wonderful new friends you’ll make in our community!

Enjoy #1 Beach in the Entire Country

Yet again, the independent expert reviewers at TripAdvisor have ranked Siesta Key beach as the #1 beach in the entire country — ahead of beaches in Clearwater, St. Pete, Maui and Honolulu. In fact, Siesta Key beach was the only U.S. beach to be ranked among the top 25 beaches in the world. It simply doesn’t get any better than that, and it’s all here for you to enjoy day and night.

Exclusive Member-Only Amenities and Benefits

When you choose to stay in our acclaimed Siesta Key beachfront vacation rentals, you’ll be entitled to a full range of exclusive member-only amenities and benefits, including access to 8 tennis courts, two club houses, three swimming pools, and so much more. For a complete look at the upscale amenities that await you, please click here.

There’s Always Something to Do!

If your goal is to relax, unwind, “get off the grid” and escape to paradise, then you can have a life-changing experience without leaving the Gulf and Bay Club. It truly is your very own private oasis. Yet if you do feel like stepping out for fun and adventure, there’s an endless variety of things to do just minutes away: shopping, dining, fishing, boating, snorkeling, sightseeing, hiking, exploring wetlands and natural parks, spotting wildlife in its natural habitat…and the list goes on! There’s always something exciting and unforgettable to experience.

Upscale Rentals at Reasonable Prices

Our stunning, professionally serviced and meticulously clean Siesta Key beachfront vacation rentals are available in 3, 4 and 5-star packages to fit your preferences and budget. In addition, you’re under no obligation to rent for an entire season. You can conveniently rent by the month any time of year, from January through to December. Simply browse our inventory to see what is available in your desired date and price range.


We’re All About Families

At Gulf and Bay Club, our team is relentlessly committed to ensuring that all of our valued members and their guests enjoy a wonderful, memorable and safe experience. That’s why we’re committed to maintaining a family-friendly atmosphere that is sophisticated and luxurious, yet also fun and down-to-earth. That’s why so many families who rent with us make new friendships that last a lifetime — and we bet you will, too!

To discover more about our Siesta Key condo rentals, please browse our online inventory. We have many high-resolution pictures and floor plans to help you choose the ideal rental unit.  

We also have a limited number of condos for sale, for both personal enjoyment, and for investors who want to add an upscale property to their portfolio.