A Guide to the Grill and Bar Scene in Siesta Key

Siesta Key has an often rambunctious and always interesting bar and grill scene. From craft beer-focused cafes to restaurants with nightly live music, there’s a little something out there for every kind of vacationer. Below we cover our top eight favorite restaurants with a bar in Siesta Key.

  • Turtle Beach Grill
  • Siesta Key Oyster Bar
  • Gilligans Island Grill
  • O’Leary’s Tiki Bar & Grill
  • The Cottage
  • The Hub Baja Grill
  • 3.14 Pi Craft Beer
  • Old Salty Dog

Siesta Key is located off the coast of Sarasota on the western side of Florida. It houses all the above restaurants and many more! So what makes each restaurant special? What’s the top dish and how far is each one from our nearby Siesta Key penthouse condos? Take a look at each spot and find the best one for you.

Ahi tuna appetizer at Turtle Beach Grill

Turtle Beach Grill

We love the thick tropical themes and neighborhood friendly atmosphere of Turtle Beach Grill. The restaurant is appropriately named- it sits right by the idyllic Turtle Beach. Happy Hour is from 3 p.m. to 6 p.m. and it is located at 8865 Midnight Pass Rd. The family atmosphere and dog-friendly patio make it a great space for all.

Siesta Key Oyster Bar

Unsurprisingly, this oyster bar is renowned for its variety of raw oysters. The Old Florida décor and tall deck seating will welcome just about anyone seeking a casual spot to dine on excessive quantities of local seafood. Oyster enthusiasts can rejoice, but everyone else can still find many American food staples, like chicken wings, jalapeño poppers, mozzarella sticks, and burgers galore.

Gilligans Island Grill

Between the tiki torches, the captivating straw and wood-heavy décor, and the tiki torch natural lighting, Gilligans Island Grill is an ideal stop for couples and romantics. The restaurant is bustling with energy late into the night. For about 14 years, Gilligan’s has been welcoming visitors with its famously-tasty homemade salsas and sauces. It is located at 5253 Ocean Blvd.

Frozen cocktail at Olearys tiki bar and grill in siesta key

O’Leary’s Tiki Bar & Grill

O’Leary’s is a wonderful bar and grill if you just love being right up by the Siesta Key beaches. Admire the glorious Gulf of Mexico as you chow down on Bleu Cheese & Bacon, Swiss & Mushroom, and even some of the best vegetarian burgers on the island.

The restaurant has live music most days, from noon to 3 p.m., and is a perfect stop for visitors due to its beachfront beauty. It is located at 5 Bayfront Dr.

The Cottage

The Cottage is a romantic diner-type atmosphere, trading off casual bar vibes for a romantic and tropical atmosphere. While the food can take a bit, it is worth every minute you wait. Try the wonton Tuna Tacos. It is located at 153 Avenida Messina.

Famous margaritas being made at the Hub Baja Grill in Siesta Key

The Hub Baja Grill

Enjoy The Hub Baja Grill’s two best features: the live music and the awesome margaritas. This local favorite is located at 5148 Ocean Blvd. grabbing a margarita at the Hub is a “must check off” Siesta Key bucket list item. (music, not sure if it’s live music)

3.14 Pi Craft Beer

Few locations capture tasty and inventive craft beer better. The casual surf style of 3.14 Pi Craft Beer is intoxicating. The menu includes quality pizza, like the Sunset, the Gulf, and the Pelican. You can also order online and pick it up online. Gluten-free options are available.

Old Salty Dog

Old Salty Dog has this colorful and fun style. It’s bright, casual, and great for families in the afternoon. This British pub also famously welcomes all pets of all sizes. Bring your pup along for a casual and cool afternoon on the island. It can be found at 5023 Ocean Blvd.

This is our definitive Siesta Key bar and grill dining guide. But check back often for updates, specific restaurant highlights, and more details on top local attractions and activities. Enjoy any of our beachfront vacation condos and experience a vacation escape like no other.


Our Location

Crystal Sands Condominiums
6300 Midnight Pass Road
Siesta Key, FL 34242

Toll-Free: 888-419-1446
Local: 941-349-7007

Fax: 941-346-1963

Stay Connected


  • NAME
  • JOIN OUR NEWS LETTER!