Sarasota County · Southwest Florida Gulf Coast
Siesta Key & Longboat Key
Two islands, one county, very different quiet.
Find Siesta Key & Longboat Key homes for sale — on-market and off.
| Price range | County | Beach | Access |
|---|---|---|---|
| $500K – $20M+ | Sarasota + Manatee | Tripadvisor’s #1 in the U.S. | Bridges from Sarasota |
See what's actually
for sale in Siesta Key & Longboat Key.
Beachfront estates and Gulf-view residences across Sarasota's two signature barrier islands — the top of the market only.
- —Beachfront & Gulf-view
- —$6M+
- —Active & coming soon
- —Siesta Key / Longboat Key (34242 / 34228)
45 listings · updated 07/24/2026
View live Siesta Key & Longboat Key listings Every other pocket on this coastListings are provided through Stellar MLS via OneHome. Buyers are represented by Sabatino Campilii, Realtor®, brokered by LoKation® Real Estate.
What makes Siesta Key & Longboat Key different?
Siesta Key and Longboat Key are Sarasota County's two signature barrier islands, and they could not feel more different. Siesta Key is the beach town — quartz-white sand ranked the best beach in the United States by Tripadvisor, a walkable Village of open-air bars and shops, and condos and cottages packed onto a small footprint. Longboat Key, a few miles north across Sarasota Bay, is the quiet one: a single low-rise road of golf clubs, guard-gated communities and Gulf-front condominiums that runs so far north it crosses out of Sarasota County into Manatee County.
Both islands are barrier islands with genuinely limited land, which keeps inventory tight in different ways — Siesta Key on turnover of small, prized lots close to the sand, Longboat Key on its own zoning, which caps building height and density and has kept the island low-rise for decades. Buyers choose Siesta Key for the beach and the walk-everywhere pace, and Longboat Key for privacy, golf, and water on both sides of a very narrow island.
- — Siesta Key Beach — Tripadvisor’s #1 U.S. beach, 2025
- — 99% quartz sand, cool underfoot even at midday
- — Longboat Key Club golf, tennis & marina
- — St. Armands Circle shopping, one bridge north
Siesta Key & Longboat Key homes for sale
- Price range
- $500K – $20M+
- County
- Sarasota + Manatee
- Beach
- Tripadvisor’s #1 in the U.S.
- Access
- Bridges from Sarasota
For buyers focused on investment:Longboat Key's decades-old low-rise zoning and Siesta Key's Tripadvisor-ranked beach both work the same way for owners — land that can't be replaced and can't be built taller, which is the whole case for durable coastal value here.
See also: Nokomis & Casey Key homes for sale.
What Siesta Key & Longboat Key actually is.
5,454 (Siesta Key, 2020) + 7,505 (Longboat Key, 2020)
Two separate Census geographies: Siesta Key is a Census-designated place (CDP) entirely in Sarasota County; Longboat Key is an incorporated town split between Sarasota and Manatee counties, up from 6,888 residents at the 2010 Census.
Source: U.S. Census Bureau, 2020 Census, 2020
Siesta Key is a small, densely built beach community of cottages, condos, and a walkable village, connected to the mainland by two bridges (Siesta Drive and Stickney Point Road) since 1917 and 1927. Longboat Key is a longer, narrower island of low-rise condominiums, golf communities, and guard-gated neighborhoods running along Gulf of Mexico Drive (State Road 789), almost entirely zoned against high-rise development, with its southern tip in Sarasota County and its northern reach crossing into Manatee County.
Both islands sit just west of downtown Sarasota. Siesta Key connects to the mainland via Siesta Drive and Stickney Point Road; Longboat Key connects south to St. Armands Key and Sarasota via the John Ringling Causeway, and north to Anna Maria Island via Longboat Pass. Sarasota–Bradenton International (SRQ) is the nearest airport, roughly 15–20 minutes from either island.
Siesta Key Village and Turtle Beach cover casual, walkable dining and public beach access; Longboat Key's dining runs mostly through the Longboat Key Club and a handful of Gulf-front restaurants, with St. Armands Circle just across the bridge for a wider mix of shopping and restaurants. Boating, golf, tennis, and shelling round out both islands' everyday recreation.
Ready to see what's actually for sale in Siesta Key & Longboat Key?
Two barrier islands, ten minutes apart, and almost opposite personalities. Siesta Key runs on beach time — mornings on the quartz sand, lunch at the Village, sunset drum circle at Siesta Beach. Longboat Key runs quieter: a tee time, a bike ride down Gulf of Mexico Drive, dinner reservations at the Club. Both are a short bridge from downtown Sarasota, St. Armands Circle, and Southwest Florida's arts and culture scene.
Siesta Key Beach
Siesta Key Beach was named the No. 1 beach in the United States by Tripadvisor's 2025 Travelers' Choice Awards, and fourth in the world. The sand is famously 99% pure quartz, ground down from the southern Appalachians over millennia, which keeps it bright white and cool underfoot even in the height of summer.
Siesta Key Village
A few walkable blocks of open-air restaurants, tiki bars, and shops just back from the beach — the closest thing the island has to a downtown, and the reason so much of Siesta Key's real estate is built around walking rather than driving.
Longboat Key Club
The private resort community that anchors the south end of Longboat Key, with two 18-hole golf courses, a marina, and tennis and pickleball courts. It's the centerpiece of the island's country-club pace and one of the reasons buyers pay a premium for Longboat over its neighbors.
St. Armands Circle
One bridge north of Longboat Key and a short causeway from Siesta Key's mainland side, St. Armands Circle is Sarasota's landmark shopping and dining roundabout — boutiques, restaurants, and the historic Ca' d'Zan and Ringling estate nearby on the same barrier chain.
Boating Sarasota Bay & the Intracoastal
Both islands front the Intracoastal Waterway on their bay side, with marinas, private docks, and quick access to Big Pass and New Pass into the Gulf — a draw for owners who want a boat as much as a beach.
Turtle Beach & Point of Rocks
South of the Village, Turtle Beach and the rocky outcrop at Point of Rocks offer a quieter, less crowded stretch of Siesta Key with some of the best snorkeling and shelling on this part of the coast.
Neither island has a true downtown of its own — Siesta Key Village is the closest thing, a compact strip of restaurants and shops near the beach, while Longboat Key has none by design. St. Armands Circle, one bridge north of Longboat, and downtown Sarasota, a short drive over the Ringling Causeway or US-41, cover the rest.
Siesta Key offers walk-to-beach retirement living with a real village center; Longboat Key offers a quieter, golf-and-marina country-club pace with less foot traffic and more privacy.
Families get a genuinely great, lifeguarded beach on Siesta Key and Sarasota County schools on the mainland a short bridge away from either island; Longboat Key's pace suits families who want space and quiet over nightlife.
Siesta Key's Tripadvisor-ranked beach and Longboat Key's decades-old low-rise, low-density zoning both restrict future supply — the scarcity argument here is durable and well documented, not speculative.
Public-school zoning and ratings change, and Longboat Key's northern tip crosses into Manatee County, which can mean a different school district depending on the exact address. These are the generally zoned Sarasota County schools as of 2026 — confirm the current assignment for a specific address with the district before relying on it.
Sarasota County Schools school locator →
School District of Manatee County school locator →
School assignments and attendance boundaries are set and changed by the school district, not by OceanFL or by any specific listing. Verify the current assignment for any address directly with the district before relying on it. OceanFL does not rate, rank, or endorse schools.
Siesta Key generally feeds Southside Elementary, Brookside Middle, and Riverview High, all rated highly on Niche and GreatSchools. Longboat Key households should confirm zoning directly, since the island's Manatee County portion can zone into a different district than its Sarasota County portion.
Longboat Key's decades-old low-rise zoning and Siesta Key's Tripadvisor-ranked beach both work the same way for owners — land that can't be replaced and can't be built taller, which is the whole case for durable coastal value here.
Siesta Key suits families who want to walk to a genuinely great beach; Longboat Key suits families who want quiet, golf, and water on both sides of the house, with Sarasota's schools, shopping and downtown a short bridge away either way.
Market commentary for general information only — not investment, tax, or legal advice, and not a guarantee of value, appreciation, or rental performance. Confirm specifics with the appropriate licensed professional.
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