Siesta Key

Occupying a barrier island in the Gulf of Mexico off the coast of Sarasota, Siesta Key is home to Siesta Beach, rated the No. 2 beach in the United States by TripAdvisor’s Traveler’s Choice Awards in 2023 and known for its white quartz sand. “Many people find that the sand has a certain energy,” says Dawn Bear, a Realtor with William Raveis Real Estate. While Siesta Beach is destination for travelers, it is also central to the experience of living on the island. “Siesta Key is just a very carefree, wonderful, stress-free community,” says Bear. “It feels like you’re on vacation year-round. And there’s always a friendly person looking to talk to you.”

Siesta Key stretches for 8 miles from its northern tip to its southern tip, but most of the activity on the island and most of its homes are on the north end. Activity centers around the downtown area and the quaint village district. “It’s a strip of local flavor with unique shops and unique restaurants. It has everything from nightclubs to a post office,” says Bear. “Whatever you’re into, you can just walk into the village and find your people.” The centralized location for retail and dining provides convenient access for residents, who can traverse all of Siesta Key with relative ease. “It has great walkability, and the trolley takes you up and down the island,” says Bear.

Houses include modern styles, Spanish Mediterraneans, ranch-style homes, cozy cottages and coastal-style homes--sometimes all on the same block. Siesta Key also has several condominium complexes and 55-plus communities that feature amenities including pools, tennis courts and, of course, access to the island’s beaches. One-bedroom condos start at around $420,000, while two-bedroom condos are typically in the $550,000 to $600,000 range. Single-family homes generally range from $1 million to $1.5 million, though there are many larger four-bedroom homes that are priced at well over $2 million.

The village is the commercial hub of the island and among the featured shops along Ocean Boulevard are Casa Del Sol Boutique, which sells stylish beachwear for men and women; and Beach Bazaar, which sells a collection of items for a more laidback island vibe. There are plenty of dining options in the village as well, but many of the local favorites are roughly 3 miles south along the Midnight Pass corridor. Toasted Mango Café is known for its inventive breakfast menu and casual setting, Miguel’s is an upscale French restaurant run by the same family since its opening in 1983, and Captain Curt’s Crab & Oyster Bar is an Old Florida eatery that serves an award-winning clam chowder. “When I have family here, which is a lot, they always have to go to Captain Curt’s,” says Bear, who has lived on Siesta Key since 1988.

In addition to the sand, the sun and the swimming, Siesta Beach also has tennis and volleyball facilities, a playground, a full-service concession stand and beach wheelchairs. The island also includes Crescent Beach, billed as “the most private non-private beach in town,” and Turtle Beach, a smaller beach with darker sand where you can fish in the nearby lagoon.

Out-of-Door Academy, a private school serving students in prekindergarten through 12th grade, is the only school on the island. Students are zoned into Sarasota County Schools institutions and can attend Southside Elementary, Brookside Middle and Riverview High schools on the mainland. All are top-rated, with A scores on Niche, and Riverview High features its own performing arts center.

There are two access points to reach the nearby mainland. The Siesta Key North Bridge connects directly to central Sarasota. The Publix-anchored Shops at Siesta Row are a mile away once you cross the bridge. The Stickney Point Bascule Bridge connects directly to south Sarasota. The U.S. 41 dining and retail corridor is less than a mile away after the bridge crossing. And the Sarasota Bradenton International Airport is just 10 miles north of the island.

Written By

Matt Pallister

Photography Contributed By

Kristjan Veski

Video By

Victoria Sharpe