Anna Maria Island and Siesta Key are both Gulf islands reached by drawbridges, both have a free trolley, and both have beaches people travel for. The biggest difference for a buyer is local government. Anna Maria Island is split into three incorporated cities in Manatee County, each with its own rules, while Siesta Key sits in Sarasota County, where the county runs Siesta Beach.

That difference shapes rental rules, permitting and who you call with questions. Here’s how the two islands line up on the things that affect owning a home there.

Anna Maria Island vs Siesta Key at a glance

How are the two islands governed?

Anna Maria Island is three cities, and Siesta Key is not organized that way. Manatee County lists the City of Anna Maria, the City of Bradenton Beach and the City of Holmes Beach among its incorporated municipalities (Manatee County). Each city has its own code of ordinances, its own vacation rental rules and its own building records.

On Siesta Key, Sarasota County runs Siesta Beach through its parks department (Sarasota County Parks). For a specific home, confirm with Sarasota County which jurisdiction’s rules apply to the parcel before you rely on them.

For a buyer, the practical upshot is simple. On Anna Maria Island, the city line can change your rental and building rules from one block to the next. On either island, the address decides which office you’ll deal with.

How do the beaches compare?

Siesta Beach is the better-known name, and Sarasota County says why. Its park page describes “nearly 100% quartz-crystal sand, dubbed the ‘world’s finest, whitest sand’,” which the county says “never gets hot under the Gulf Coast sun” (Sarasota County Parks).

The county’s page also lists the awards. It credits Dr. Beach with naming Siesta Beach the #1 beach in America in 2011 and 2017, and U.S. News and World Report with ranking it #1 in Best U.S. Beaches in 2026. It adds that Siesta Beach’s 950 free parking spaces are the most at any public beach in Sarasota County.

Anna Maria Island’s public beaches are spread along the island. Manatee County’s beach list includes Manatee Public Beach, at State Road 64 and Gulf Drive in Holmes Beach, open sunrise to 10 p.m., and Coquina Beach, at 2650 Gulf Drive in Bradenton Beach, open sunrise to sunset (Manatee County).

Which beach suits you is personal. The useful comparison for an owner is how you’ll get to the sand from a particular house, and what the parking and access look like there.

How do you get around each island?

Both islands run free trolleys, and both are reached by drawbridges.

The trolleys

Manatee County says the free Anna Maria Island Trolley runs from 6:00 a.m. to 10:30 p.m. seven days a week, 365 days a year. It serves Gulf Drive between the Anna Maria Island City Pier and Coquina Beach every 20 minutes (Manatee County Area Transit).

On Siesta Key, Sarasota County says the Siesta Key Breeze runs from Siesta Village to the southern end of the island and back. Rides are free, and it operates from 8 a.m. to 10 p.m. every day, with modified hours on some holidays.

The drawbridges

Federal rules set when the bridges open for boats, which affects drive times too (33 CFR 117.287):

• Anna Maria Island. The Cortez (SR 684) Bridge and the Anna Maria (SR 64) Bridge open on signal, except that from 6 a.m. to 7 p.m. daily they need only open on the quarter hour and three-quarter hour.
• Siesta Key. The Stickney Point Bridge and the Siesta Drive Bridge open on signal, except that from 6 a.m. to 7 p.m. daily they need only open on the hour and half hour.

If you’ll keep a boat, check the full route from a particular dock to open water, including any fixed bridges, against your boat’s height before you buy.

Can you rent out a home on either island?

On both islands, state law sets the outer limits. Florida says a local law “may not prohibit vacation rentals or regulate the duration or frequency of rental of vacation rentals,” except for local laws adopted on or before June 1, 2011 (Florida Statutes s. 509.032).

On Anna Maria Island, the three cities then set different rules:

• Anna Maria caps vacation rental occupancy at the lesser of a bedroom-based formula or eight occupants (City of Anna Maria, Chapter 108).
• Holmes Beach requires a Vacation Rental Certificate for all rental properties and sets minimum rental periods by zoning district, including 30 days in R-1 and weekly rentals in R-2, R-3 and R-4 (City of Holmes Beach).
• Bradenton Beach requires a state lodging license, a business tax receipt and a city Transient Public Lodging Establishment License (City of Bradenton Beach, Chapter 59).

On Siesta Key, check the rules with Sarasota County for the specific parcel, along with any condo or homeowners’ association documents. On either island, rental income depends on the address as much as the house.

Are both islands in flood zones?

Check the address on both. On Anna Maria Island, two of the three cities say every property is in a Special Flood Hazard Area, the zones FEMA maps for a 1-percent-annual-chance flood. Holmes Beach’s flood page says “ALL PROPERTY IN HOLMES BEACH FALLS WITHIN A SPECIAL FLOOD HAZARD AREA!” (City of Holmes Beach), and Bradenton Beach says the same of every property in that city (City of Bradenton Beach).

For the City of Anna Maria and for Siesta Key, look up the specific property through the county or FEMA’s flood maps. Get a flood insurance quote for the address before you make an offer on either island.

How should you choose between them?

Compare the things that change what a home costs and what you can do with it, rather than the reputation of the island:

1. 1
   Jurisdiction. Which city or county rules apply to the parcel?
2. 2
   Rental plans. What do the city, zoning and association documents allow?
3. 3
   Flood status and insurance. What’s the zone, and what does a quote look like?
4. 4
   Access. How far is the house from the bridges, the trolley and the beach you’d use?
5. 5
   Boating. Does the route from the dock to open water work for your boat?

If Anna Maria Island is on your list, our Anna Maria Island homes for sale page covers its three cities. For the other island, see Siesta Key homes and condos for sale.

Frequently asked questions

Sources

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• Manatee County, Manatee County Area Transit and incorporated municipalities list, retrieved 2026-10-21, https://www.mymanatee.org/manatee-county-area-transit
• Manatee County Area Transit, “Ride Route 5 – Anna Maria Island Trolley,” retrieved 2026-10-21, https://www.mymanatee.org/services-and-amenities/service-listing/service-details/ride-route-5-anna-maria-island-trolley
• Manatee County, “Boat Ramps and Beaches,” retrieved 2026-10-21, https://www.mymanatee.org/connect/locations/boat-ramps-and-beaches
• Sarasota County Parks, “Siesta Beach,” retrieved 2026-10-21, https://www.sarasotacountyparks.com/parks-and-facilities/discover-a-park/destination-parks/siesta-beach
• 33 CFR 117.287, “Gulf Intracoastal Waterway,” retrieved 2026-10-21, https://www.ecfr.gov/current/title-33/chapter-I/subchapter-J/part-117/subpart-B/section-117.287
• Florida Statutes s. 509.032, retrieved 2026-10-21, https://www.leg.state.fl.us/statutes/index.cfm?App_mode=Display_Statute&URL=0500-0599/0509/Sections/0509.032.html
• City of Anna Maria, Code of Ordinances, Chapter 108, retrieved 2026-10-21, https://library.municode.com/fl/anna_maria/codes/code_of_ordinances?nodeId=PTIICOOR_CH108VARE
• City of Holmes Beach, “Vacation Rental Certificates” and “Flood & Hurricane Protection Information,” retrieved 2026-10-21, https://www.holmesbeachfl.org/departments/vacation_rental_certificates.php
• City of Bradenton Beach, Code of Ordinances, Chapter 59, and “Flood Protection Information,” retrieved 2026-10-21, https://www.cityofbradentonbeach.com/174/Flood-Protection-Information

This comparison summarizes public information as published on the retrieval date. Confirm the rules, flood status and insurance for a specific property with the relevant city or county and your own advisers.