After spending the day in the Florida sun or on the beach, you may be ready to enjoy the vibrant nightlife that Siesta Key has to offer. If you’re looking to relax with a few drinks and some delicious pub food, Siesta Key is home to several great places with live music, charming decor, and party atmospheres.
Book your stay with Siesta Key Dreams to make the most of this wonderful island’s spirit.
These Siesta Key bars are some of our favorite places to get great drinks, fun entertainment, and lively atmosphere.
1. Daiquiri Deck Siesta Key Village
- Website: daiquirideck.com
- Hours: Daily 11 AM – 11 PM
- Address: 5250 Ocean Blvd
This beach-inspired location is a casual hotspot located in the heart of Siesta Key Village and it offers happy hour daily from 3 – 7 PM!
As the name suggests, frozen daiquiris are the speciality, ideal for hot days during summer visits or anyone craving sweets. Wine, beer, seltzers, and a variety of other cocktails are also served. Daiquiri Deck offers brunch and dinner menus as well, featuring tacos, burgers, salads, and fish.
Daiquiri Deck was created in the 90’s by a local lifeguard who wanted to create the perfect paradise to end a day on the sand. This establishment is definitely an oasis for positive vibes and delicious cocktails.
2. Gilligan’s Island Bar
- Website: www.gilligansislandbar.com
- Hours: Daily from 11 AM – 12 AM (Kitchen closes at 10 PM)
- Address: 5253 Ocean Blvd
Founded in 2001, Gilligan’s Island Bar & Grill is located in Siesta Key Village and offers quality food, cocktails, and service. You’ll notice Gilligan’s immediately from its tiki bar and thatched roof at the front of the location. Inside, there is a VW Bus parked in front of the kitchen, which creates a certain old Florida charm that cannot be beat.
This location offers live bands that play from 6 PM on weekdays and 1 PM on weekends right on the front deck. The live music really adds to the uplifting feel of this bar, so don’t miss out.
Exclusive cocktails are offered in custom Gilligan’s tiki mugs. Beer, wine, and cocktails are also available at this unique establishment. The kitchen serves up hearty grub, like burgers, sandwiches, and rice bowls, for lunch and dinner.
The food at Gilligan’s is great, but if you love fresh seafood, Siesta Key Oyster Bar is just across the street, and it serves up incredible shellfish.
3. Big Tiki Lounge
- Website: thebigtikilounge.com
- Hours of Operation: Daily from 11 AM to 9 PM
- Address: 5311 Ocean Blvd
Big Tiki Lounge perfectly captures the laid-back island vibe. Nestled just steps from the beach, this tiki bar offers a vibrant atmosphere with its signature bamboo décor, tiki torches, and lively music that keeps the good times rolling.
Whether you’re settling in for a sunset cocktail or a late-night drink, Big Tiki Lounge’s welcoming vibe makes it the perfect place to unwind and soak up the tropical spirit. Be sure to grab tickets to its lively NYE Party if you’ll be spending New Year’s in Siesta Key.
What truly sets Big Tiki Lounge apart are its standout drinks, especially the tropical rum cocktails like the Mai Tai and the refreshing Coconut Mojito. Their creative use of fresh ingredients and house-made mixers elevates every sip, making it a favorite among locals and visitors alike.
Add in friendly bartenders, occasional live music, and fun events like karaoke nights, and you’ve got a must-visit spot that’s as memorable as Siesta Key itself.
4. Crescent Club
- Website: crescentclubsiestakey.com
- Hours: Daily 10 AM – 2 AM
- Address: 6519 Midnight Pass Rd
Opened in 1949, this establishment has classic old-fashioned decor and a variety of liquor, beer, and wine on offer. One of the most original Siesta Key drinking bars, it features a shaded, outdoor patio with plenty of tables and seating, as well as two bars to sit at as well.
One of the most fun aspects of this location is that there is a full drive-thru with packaged liquor, beer, and wine that you can take to go. If you don’t have time to stop in and say hello, the drive-thru is an easy option so you can still get a taste of this local establishment.
Live music plays at 7 PM daily so if you’re in the mood for dancing or want to listen to local talent, join the fun at Crescent Club. The casual atmosphere is incredibly inviting to locals and tourists alike.
Unlike the other bars on this list, Crescent Club isn’t located in Siesta Key Village. You’ll find it further south, close to Stickney Point Road that connects Siesta Key with South Sarasota.
Experience Local Nightlife While Visiting Siesta Key
Siesta Village is barely a 3-minute walk away from most Siesta Key Dreams rental properties, making it easy to immerse yourself in the lively nightlife of this bustling area. You can find even more great places to hang out at local restaurants nearby.
Book your trip today and get ready to dance the night away in Siesta Key.
