Discover Why Guests Love Staying on Siesta Key

At Gulf & Bay Club Bayside, our guests come for the beach—but they return for the experience. Nestled along the bay just across from world-famous Siesta Key Beach, our charming resort has become a favorite destination for couples, families, and snowbirds alike. From our beautifully maintained vacation rentals to the peaceful setting and resort-style amenities, visitors consistently rate us as one of the best places to stay on Siesta Key.

Why Guests Keep Coming Back

Gulf & Bay Club Bayside is more than just a vacation rental—it’s a resort-style community where comfort, location, and amenities come together to create the ideal Siesta Key experience.

Guests love:
Private deeded beach access to America’s #1 beach, just steps away
Two heated swimming pools
Tennis courts and pickleball
A modern fitness center with sauna
Lush, tropical landscaping with Old Florida charm
Friendly, responsive management
Proximity to Siesta Key Village, restaurants, and shopping

Your 5-Star Siesta Key Vacation Starts Here

Don’t just take our word for it—see why so many guests return to Gulf & Bay Club Bayside year after year. Our collection of glowing reviews is proof that when it comes to Siesta Key vacation rentals, we’re one of the best in the area.

Ready to experience it for yourself?
Visit gulfandbaybayside.com to browse available condos and start planning your next island escape.

Gulf & Bay Club Bayside – Your Home Away From Home on Siesta Key.

What Our Guests Are Saying

Absolutely wonderful

My girlfriend and I enjoyed this place so much, we would definitely consider returning next year. The place was absolutely wonderful, as was the private beach access we had as well. The photos looked exactly like the interior, as well as the outdoor amenities as well. It truly felt like a home away from home.

By: Matthew

Excellent

Great, beautiful, the best, our new address for vacation in Florida Thanks!!!

By: Tomas

1346-Siesta Key

The condo was lovely and the master bedroom bed was super comfy. Close to beach with private beach access across the street. You cannot drive over to the beach so be prepared to walk. The great thing about the condo is that a wagon is provided which helps getting all your stuff to the beach. You have a nice little view of the bay from the balcony. The property grounds and pools are very well kep

By: Mandy

Very nice place.

Easy check-in and check out instructions, with reminder txts. Location was great. Outdoor seating was my favorite spot. Beach access is a huge advantage of this place! My friends stayed one block from me in the building, that did not have one and it was a big problem for them. Office was always responsive. Pools and facilities were clean. I will come back.

By: Alona

Absolutely loved this place!

Was a perfect walking distance to the beach and only a few minute drive into town for the morning coffee and to walk the local markets! will absolutely be booking with these guys again! the kitchen had everything that you could think of needing for a week's stay! the condo was very clean and kept up well! I will be back!

By: Austin

We really enjoyed staying at Gulf and Bay Bayside.

We wanted to try a new place this year and we were happy with it. There was very beautiful sceneries between the houses, very spacious/ plenty of room and the pool was very inviting and refreshing. It was also fun bird and turtle watching at the pond. Everything was so convenient and easy to get to! We would definitely stay again! :-)

By: Brandy

We had the best time at the house we stayed in!

It was very clean and very homey. We had a wonderful week there.

By: Marissa

A very enjoyable vacation!

We will be back and we will bring our family!

By: Heather

Nicest VRBO rental so far.

If you want a two bedroom and two bath unit on Siesta Key with gulf access book this unit. You’ll encounter a recent high end renovation. This unit has everything, the nicest rental I’ve booked so far.

By: Louis

Awesome!

The space is awesome, very close to everything. The condo was extremely clean and spacious. Everyone slept well. Would definitely stay here again.

By: Brooke