Siesta Key Village Entertains & Charms – Both Day & Night

Named #1 beach in the U.S. and #4 globally by TripAdvisor's 2025 Travelers' Choice Awards, Siesta Key is known for its crystal-quartz (and gorgeous) white-sand beaches and an eclectic, local-casual vibe. 

What locals know and visitors soon discover upon landing on Siesta Key is a small downtown (a few blocks from our famed beach) that caters to all of their other-ly pursuits from sun up to way past sundown. 

Once beach-time is done (or you've had your fill of sun), transition from sand to an entertainment paradise just steps away at Siesta Key Village – or as locals call it, “The Village.”  With more than 100 shops, bars, restaurants and hotels of every style and type, the options seem limitless.

Where to Dine

For family, friends and even the newly-acquainted, Siesta Key Village plays host to every sort of dining experience – from fine wine and white-cloth to beachy tiki hangouts and everything in between. A few worth mentioning of many:

• Siesta Key Oyster Bar ("SKOB")– Cold draft beers, pitchers of cocktails, live music and happy hour oysters galore, who could say ‘no’ to that?
• Café Gabbiano – Dine in for elevated Italian with farm-to-table ingredients and a wine bottle collection of thousands.
• The Old Salty Dog – Enjoy Gulf-caught seafood dishes and the famous "salty (hot) dog" at this neighborhood favorite.
• The Cottage – Don't miss the hidden outdoor back patio, where live music enhances the high-end tropical vibe and craft cocktails pair well with the global menu.
• Blasé Martini Bar – Just before turning onto Beach Avenue, stop into this hot spot for a piece of pizza, martini and craft beer. 

• Village Café – Start the day the right way at this family-owned and friendly breakfast stop.

   

Where to Shop

Whether you’re shopping for silky resort wear or getting suited up for the sand, Siesta Key Village shops deliver:

• Gidget’s Coastal Provisions – Looking for a unique souvenir? This longstanding boutique is chock full of everything you want in a coastal specialty shop, from local art and home decor to kids toys and kitschy gifts.
• Foxy Lady – Women find this trend-setting, high-fashion boutique to be their go-to for any Siesta soiree.
• Casa Del Sol – Men can find their fashion boardies and sunglasses while women can secure a perfect pair of swimmers and coastal jewelry.
• Beach Bazaar – 6,000 square feet of shopping bliss for the whole family, find a new pair of sandals or a boogie board for the beach.

• Morton’s Siesta Market – Grab some groceries, provisions, florals, cigars, alcoholic beverages and more down at the local market.

   

What to Do

The options for being active or taking a chill along Ocean Boulevard (Siesta Village’s “main street”) are many. A couple worthy of attention are…

• Shop the Farmers Market – Check out the weekly Siesta Key Farmers Market from 9am to 2pm for fresh-pressed juices, organic produce, tacos, crafts, Siesta Key Rum and much more with an island vibe.
• Grab Morning Coffee – Stop by the mini stand for a cup of joe and cinnamon sugar donuts at Meaney's Mini Donuts & Coffee House, order a flavored latte at MOJO Risin' Coffee Co. or try the fair-trade beans at Bean Coffeehouse.
• Get Some Ice Cream – What better way to top off your day than with a scoop of ice cream? Choose from multiple local shops, including Made In Rome Organic Gelato, Big Olaf Creamery, Kilwin's Ice Cream & Fudge, and Curly Cream Hand Rolled Ice Cream.
• Take a Pilates Class – Fit fitness into your vacay at Siesta Key Pilates, which offers small group reformer classes to challenge your limits.

• Get a Tattoo – Go home with a permanent memory by the local artists at Rose and Dagger Tattoo Studio.

   

Bar Hopping

Craft cocktails, Florida beers, local singers and jam bands dot Ocean Boulevard and the side streets that encompass the Village – not to mention the people-watching entertainment that ensues on a night out on the Key:

• Daiquiri Deck – There aren't many better places to post up after a long day in the sun than at the wildly popular daiquiri bar, which features dozens of frozen fruit flavors and rum options. 
• Gilligan's Island Bar & Grill – Enjoy happy hour deals, playing darts in an open-air dive bar setting and live music under the giant hatched tiki roof.

• The Beach Club – A hot nightclub spot for locals and visitors alike, put your dancing shoes on for a rotating roster of live bands, DJs and weekly themed nights. 

   

How to Get Around 

Walking around is easy in Siesta Key Village, and the area remains wheelchair accessible for travelers with added mobility needs. While parking can be tricky during busy hours or holidays, alternatives to driving are ideal. And sometimes, you just want a break from walking. So check out some fun (and some free) alternatives to getting around:

• Siesta Key Breeze Trolley – Siesta Key's public open-air trolley (Route 77 Siesta Islander) is free for all riders and will take you through various points of the Village from 8am to 10pm daily.
• Sarasota Bike Tours – Leave the car behind and grab alternative wheels to get around the Village. You can either rent beach cruisers and e-bikes for the day or week, or take a two-wheeled tour of the Key. 
• Robin Hood Rentals – Rent from a fleet of 1- and 2-seat motor scooters to zip around the main drag and side streets. 

• ZoomAround – Jump in your very own street-legal golf cart, with both gas and electric options of up to 4 and 6 seats.

   

Places to Stay

Lodging options vary around this area of Siesta Key. Choose from a wide variety of hotels and other stays – from casual-beachy to luxe-grand – but always be close to the action:

• Siesta Key Beach Resorts & Suites – A stay includes a lovely pool and being treated to their renovated “Big Tiki” bar and prime location in the heart of the Village on Ocean Boulevard.  
• The Cottages on the Key – Enjoy staying at fully-furnished vacation home and villa rentals—many with heated pools—situated right in the Village.
• Tropical Breeze Resort – Located a block off the main drag, chilling here is a breeze and a close jaunt to the beach.

• Siesta Key Luxury Rental Properties – From romantic retreats to family getaways, these luxury rental properties offer comfort, rooftop decks so you can see all the action and a highly walkable location to the Village.