If rental income set the price of a home on Anna Maria Island, the math would run backwards. Bradenton Beach, the one city on the island that allows nightly rentals everywhere, is the cheapest of the three. The City of Anna Maria, which requires the longest minimum stays and the most paperwork before you can rent at all, commands the highest prices. As of February 2026, the City of Anna Maria's median sale price stood at $1.625 million against Holmes Beach's $1.185 million. Bradenton Beach, the most rental-friendly city on paper, has long run below both.

That's not what an investor's spreadsheet would predict. More nights available to rent should mean more income potential, which should mean higher prices. On this island it doesn't work that way, and understanding why matters more than the median price itself if you're trying to figure out where your money actually goes.

Three Cities, Not Three Neighborhoods

Anna Maria Island runs seven miles along Florida's Gulf Coast, and it's easy to talk about it as one market. It isn't. The island is split into three separately incorporated cities: Anna Maria at the north end, Holmes Beach in the middle, and Bradenton Beach at the south end near the Cortez Road bridge. Each city writes and enforces its own zoning code, its own short-term rental ordinance, and its own inspection and registration requirements. A rule that applies in one city doesn't carry over to the next one, even though you could walk between them in twenty minutes.

That independence is the mechanism behind the price gap. Each city's rental rules shape who ends up bidding on its inventory, and the buyer pool, not the view, is what moves the median.

What Each City Actually Requires

Anna Maria's registration process is the heaviest lift of the three. Bradenton Beach's is the most permissive but comes with its own compliance list, including an occupancy cap of two people per bedroom plus two, or one person per hundred square feet, up to twelve total. Holmes Beach sits in between, and its answer to "can I rent this nightly" depends entirely on which zone the parcel sits in, not which city.

The Price Gap That Doesn't Match the Rental Rules

Pull three different figures for Holmes Beach and you'll get three different stories. The median sale price ran $1.185 million as of February 2026. By July 2026, the median list price on active inventory had climbed to $1.44 million. Average asking prices across roughly 196 active listings that same month were closer to $1.94 million. None of these numbers is wrong. They're measuring different slices of a market that ranges from older canal cottages locked into 30-day minimums to Gulf-front condos that can turn over weekly, and which properties happen to be listed in a given month swings the average as much as the underlying trend does.

The City of Anna Maria doesn't have this problem to the same degree, because its inventory is more uniform. Most of what sells there is a single-family home, and the rental restrictions filter out a large share of investor buyers before they ever make an offer. What's left bidding is a smaller, less price-sensitive pool: people buying a second home or a permanent residence who aren't underwriting the purchase against a rental income projection. A buyer who doesn't need the numbers to pencil for a cap rate calculation isn't going to walk away from a home over a few percentage points of asking price the way an investor comparing three markets would. That's a meaningful part of why the city with the strictest rental rules also has the highest median.

Bradenton Beach runs the opposite direction, and not because nightly rentals fail to add value. Its inventory is dominated by condos rather than single-family homes, and condos on this stretch of the Gulf simply carry lower price points than detached houses on comparable lots. Agents who work the island have long noted that Bradenton Beach prices run below Holmes Beach's, and the property mix, not the rental rules, is the more likely explanation. Nightly rental rights are a real amenity, but they're layered on top of a housing stock that starts from a lower base.

Zoning Changes Block to Block, Not Just City to City

The complication that catches buyers off guard usually isn't which city they're in. It's that Holmes Beach itself doesn't have one rule. Homes in the Key Royale and Bay Palms neighborhoods sit in R1 and R1AA zones, where the code sets a 30-day minimum regardless of what a listing description implies. Properties in R2 through R4 zones can be rented for a minimum of seven nights. A1 zones, which are mostly condominiums, allow nightly stays and carry the annual inspection requirement that comes with Holmes Beach's Vacation Rental Certificate program.

That means the honest answer to "can I run this as a nightly rental" only exists once you know the parcel's zoning designation, not once you know which of the three cities it's in. A buyer comparing two Holmes Beach listings a few blocks apart could be comparing a 30-day-minimum property against a nightly-eligible one, with a price difference that has nothing to do with the homes themselves.

The Cortez Bridge Just Became Bradenton Beach's Newest Variable

There's a second factor worth knowing if you're looking at the south end of the island right now. The Florida Department of Transportation is replacing the Cortez Bridge, the only vehicle connection between Bradenton Beach and the mainland at Cortez along State Road 684. Construction is set to begin in early September 2026 and is expected to run about four years, with the project's most recent cost estimate at $123 million, according to The Anna Maria Islander.

The current bridge is a bascule drawbridge built in 1956. Its replacement will be a 65-foot fixed span that eliminates the need for the bridge to open for boat traffic, a change FDOT expects will reduce the backups that build up during peak season and hurricane evacuations. The existing drawbridge is expected to stay in service during much of the four-year construction window, so this isn't a story about the road closing. It's a story about years of active construction traffic on the only route in and out of Bradenton Beach, which is a real variable for anyone weighing a rental property or a remote purchase on that end of the island right now. The Bradenton Area Convention and Visitors Bureau has said it's adding a third Gulf Islands Ferry to help absorb some of that congestion during the build.

None of this makes Bradenton Beach a worse buy. It does mean the due diligence list for a south-end property should include a look at the FDOT project page for the current construction phase, not just the usual inspection and survey items.

What This Means If You're Comparing the Three Cities

The median price gap between Anna Maria, Holmes Beach, and Bradenton Beach isn't a clean signal of which city is "better." It reflects three different rulebooks filtering three different buyer pools onto three different types of inventory. A property's rental eligibility depends on its specific zone, not its city, and that single fact can move a home's value more than its distance from the beach. If you're underwriting a purchase against rental income, the zoning designation on that exact parcel is the number to confirm before anything else, and if you're looking at Bradenton Beach specifically, the Cortez Bridge timeline belongs in that same conversation.

Frequently Asked Questions

Does buying in Holmes Beach guarantee I can rent nightly? No. Holmes Beach's rules vary by zone. R1 and R1AA areas like Key Royale and Bay Palms carry a 30-day minimum, R2-R4 zones allow seven-night minimums, and only A1 zones, mostly condos, permit nightly rentals.

Will the Cortez Bridge construction cut off access to Bradenton Beach? The existing drawbridge is expected to remain in service during much of the four-year construction period, and regional tourism officials have added a third Gulf Islands Ferry to help manage congestion. Expect active construction traffic on the only mainland connection, not a closed route.

Is the City of Anna Maria a bad choice if I want rental income? Not automatically, but the calculus is different. Longer minimum stays and an annual inspection requirement mean the numbers work best for owners who don't need the property to cash-flow like a full-time short-term rental.

Every one of these answers changes depending on the exact parcel, not just the city limit it sits inside, which is exactly the kind of detail worth confirming before you write an offer. Victoria Bouziane works these three cities block by block and can walk you through what a specific zone allows before you're under contract. Reach out to request a personalized home valuation and a straight answer on what your rental plans can actually support.