Anna Maria is the northernmost city on Anna Maria Island, sitting at the northern tip of the barrier island where the Gulf of Mexico meets Tampa Bay. It is the smallest and most residential of the island’s three cities, with a character defined by Pine Avenue — a pedestrian-oriented main street lined with independent shops, cafes, and restaurants — and a strong sense of community that makes it feel distinct from the more tourist-oriented sections of the island to its south.
The median home price in Anna Maria is approximately $2.79 million as of early 2026, down roughly 5 percent from January 2025 and 7.2 percent from peak. Price per square foot is approximately $1,235. This is a luxury market with luxury expectations — but it also has genuine short-term rental income potential that makes the economics more accessible than the sticker price suggests for investor-buyers.
Barrett Henry covers the full Manatee County market including the barrier island communities. Anna Maria Island is not a market where you learn the dynamics from a website — it requires knowing the flood zone specifics of individual streets, the STR licensing landscape, and the building and renovation constraints that apply in a coastal high-hazard area. This guide provides the essential context for anyone evaluating Anna Maria real estate seriously.
Anna Maria FL Real Estate Market Overview (2026)
The Anna Maria market in early 2026 is showing a correction from the peak values of 2022-2023. With the average home value down 7.2 percent year-over-year and the median down from prior peak levels, buyers are finding conditions more favorable than at any point in recent years. Days on market have extended, and sellers are more willing to negotiate than during the frenzy of the pandemic-era market.
The market here divides into two primary buyer motivations: lifestyle buyers who want Anna Maria as a primary residence or vacation home for their own use, and investor buyers who are purchasing primarily for short-term rental income. The two buyer types have different evaluation frameworks.
For lifestyle buyers, the evaluation centers on property condition, flood zone, Gulf or bay access, proximity to Pine Avenue, and the long-term livability of the specific street and neighborhood. For investor buyers, the STR income history, occupancy rates, rental management structure, and return on invested capital are the primary metrics. Many purchases represent a hybrid of both motivations — owners who use the property for their own enjoyment for a portion of the year and rent it out for income the rest of the time.
The short-term rental market on Anna Maria Island has seen increased regulatory attention from all three island cities since 2022. The City of Anna Maria allows nightly rentals with proper registration and licensing — an annual registration with the city and a Transient Public Lodging Establishment (TPLE) license from the Florida Department of Business and Professional Regulation (DBPR) are both required. Failure to obtain proper licensing can result in penalties of $100 to $500 per day. Buyers who are purchasing primarily for STR income must verify the specific licensing requirements and any applicable zone restrictions before closing.
Flood Risk on Anna Maria Island
The entire City of Anna Maria falls within the 100-year floodplain — it is entirely within a Special Flood Hazard Area (SFHA) with coastal high-hazard area designations for many properties. This is not a risk that can be avoided by choosing a specific neighborhood; it is a market-wide characteristic that every buyer must understand and price into their acquisition decision.
Flood insurance under the National Flood Insurance Program (NFIP) is required for all mortgaged properties in the Special Flood Hazard Area. The annual cost of flood insurance varies significantly based on the property’s elevation relative to the Base Flood Elevation, the age of construction, and the building’s specific design. Elevated newer construction generally carries lower flood insurance premiums than older ground-level structures. This is one reason why newly constructed elevated homes command significant premiums over comparable lot-level older structures — the flood insurance savings over decades of ownership can be substantial.
FEMA’s Elevate Florida program provides grants and low-interest loans for property elevation, with FEMA covering up to 75 percent of elevation costs. Costs for elevation work typically run $20,000 to $100,000-plus depending on the structure type and the amount of elevation required. For buyers considering older ground-level properties, understanding the cost and feasibility of elevation work is part of the full acquisition analysis.
Hurricane Helene and Milton’s impact on the island in 2024 reinforced the storm surge risk that barrier island buyers must account for. Bradenton Beach, at the island’s south end, experienced significant impact and is still navigating FEMA reimbursement disputes for infrastructure repairs as of early 2026. See our Florida flood zones guide for a complete explanation of what coastal high-hazard designations mean for insurance, financing, and risk management.
Short-Term Rental Rules on Anna Maria Island
The three cities on Anna Maria Island — Anna Maria, Holmes Beach, and Bradenton Beach — each have distinct short-term rental regulatory regimes, which is one of the most critical due diligence items for any investor buying on the island.
City of Anna Maria: Nightly rentals are allowed with proper annual registration and TPLE licensing from DBPR. Occupancy limits apply (2 people per bedroom over 100 square feet, 1 person per bedroom 70-100 square feet, plus 2 additional guests maximum). Taxes include 6 percent Florida state sales tax plus 5 percent Manatee County Tourist Development Tax (TDT) on rentals under 6 months. On-site parking is required, and noise ordinances are strictly enforced.
City of Holmes Beach (covered in the Holmes Beach guide): The most restrictive of the three cities for STRs. In R1 and R1 AA zones, minimum 30-day rentals only — no nightly rentals. In A1 zones, nightly rentals are allowed. Zone verification for any specific property address is essential before purchasing in Holmes Beach with STR income as a primary objective.
City of Bradenton Beach (covered in the Bradenton Beach guide): STR regulations vary by zone with registration and TPLE licensing requirements similar to Anna Maria. Bridge Street area properties have active STR markets given the tourist draw of the waterfront district.
Florida state law preempts some local short-term rental regulations, which has created an ongoing tension between state-level preemption and local municipal control across Florida’s tourist markets including Anna Maria Island. Buyers should verify the current state of the regulatory landscape with local counsel before making purchase decisions based on STR income projections.
Pine Avenue and the Character of Anna Maria City
Pine Avenue is the defining street of the City of Anna Maria — a historic main street that runs from the Gulf side to the bay side of the island’s northern tip and serves as the social and commercial heart of the city. It is trolley-accessible, walkable by island standards, and lined with restaurants, shops, and community destinations that give Anna Maria its village character distinct from the more tourist-intensive sections of the island.
North Shore Cafe at 304 Pine Avenue is a specialty cafe known for espresso drinks, smoothies, avocado toast, breakfast sandwiches, and health bowls with acai. J Burns Pizza at 308 Pine Avenue is the casual take-out pizza option. The Donut Experiment at 210c Pine Avenue handles the coffee and gourmet donut crowd. Poppo’s Taqueria on Pine Avenue brings authentic Mexican food to the walkable district. The Anna Maria Oyster Bar at 200 Bridge Street anchors the waterfront dining scene at the bridge connection to Bradenton Beach.
The family-friendly, vacation-oriented character of Anna Maria city is reflected in its retail and dining — it is not a sophisticated urban scene, but it is genuinely pleasant, community-oriented, and well-suited to both families with children and retirees who want a beach community with a sense of place. Most visitors and residents who experience it describe the quality of life as exceptional once you accept the traffic realities of a small island with large visitor demand.
Schools on Anna Maria Island
Anna Maria Elementary School, though physically located in Holmes Beach, serves the entire island and is one of the most exceptional public elementary schools in Florida. The school ranks in the top 10 percent of Florida elementary schools for overall test scores, with math proficiency in the top 5 percent (80 to 84 percent versus the state average of 52 percent) and reading proficiency also in the top 5 percent (75 to 79 percent versus the state average of 52 percent). It is ranked number 277 in Florida elementary schools overall with 207 students in grades PK through K5, a student-teacher ratio of 14:1, and hosts the Guy Harvey Academy of Arts and Sciences — Florida’s first such specialized program within a public elementary school.
For buyers with elementary-age children who are considering Anna Maria Island as a primary residence, the school quality is a genuine asset. The island is close enough to Manatee County that middle and high school options in the district are accessible, though families should verify school zone assignments for specific addresses. The island’s small size and community character create an environment that many families describe as exceptional for raising children.
Island Traffic and the Trolley System
Anna Maria Island is a barrier island accessible by two bridge causeways — the Manatee Avenue (SR-64) causeway from Bradenton connecting to Holmes Beach and the Cortez Bridge (SR-684) to Bradenton Beach at the south end. During peak season (December through April) and on summer weekends, traffic on both causeways can back up significantly, with waits of 20 to 45 minutes to cross onto or off the island. This is one of the most practical daily-life realities that lifestyle buyers need to understand before committing to island living.
The Island Trolley runs throughout Anna Maria Island and connects all three cities — it is free to ride and operates on a regular schedule during daylight hours. For residents who work or shop on the island itself, the trolley is a practical way to avoid car movement during peak hours. For commuters who need to cross the bridge daily, the traffic reality is a meaningful quality-of-life consideration that is worth experiencing firsthand before purchasing.
Anna Maria Island vs. Longboat Key
Buyers evaluating Gulf Coast barrier island options in Manatee County inevitably compare Anna Maria Island to Longboat Key. The two islands serve different buyer profiles despite sharing the same Gulf of Mexico coast.
Anna Maria Island is more casual, family-oriented, and community-focused. It allows short-term nightly rentals in Anna Maria city, has a more active and accessible beach scene on the public beaches, and has a price point that is high but below Longboat Key’s luxury tier in many segments. Anna Maria Island buyers tend to be seeking genuine beach community living — the Pine Avenue walkability, the island’s social fabric, and the Gulf access.
Longboat Key is more private, more luxury-focused, and more resort-oriented. The Longboat Key Club’s 45-hole golf complex, 20-court tennis facility, and 291-slip marina create an amenity ecosystem that Anna Maria Island does not replicate. Longboat Key caters more to the permanent luxury second-home buyer and less to the active short-term rental investor. The median at $1.18M reflects a wide range of condo options from $400,000 to over $13M.
Frequently Asked Questions About Anna Maria FL
Is Anna Maria Island a good investment?
For buyers who understand the flood risk, insurance costs, and short-term rental regulatory environment, Anna Maria Island can be a compelling investment. STR income on well-positioned island properties can be significant. The investment case requires a full underwriting of insurance costs (flood plus windstorm), maintenance reserves for a coastal property, and realistic STR occupancy projections based on actual market data — not best-case scenarios.
What is the median home price in Anna Maria FL?
Approximately $2.79 million as of early 2026, down 5 percent from January 2025. The average home value is $2.15 million. Price per square foot is approximately $1,235. This range reflects primarily single-family homes and Gulf or bay-front properties. Condominiums and smaller properties at the lower end of the range provide somewhat lower entry points.
Are short-term rentals allowed in Anna Maria FL?
Yes, the City of Anna Maria allows nightly short-term rentals with proper annual city registration and a Florida DBPR Transient Public Lodging Establishment (TPLE) license. Occupancy limits, noise ordinances, and parking requirements apply. Taxes include 6 percent Florida state sales tax plus 5 percent Manatee County Tourist Development Tax. Non-compliance penalties run $100 to $500 per day.
What is Pine Avenue in Anna Maria?
Pine Avenue is the historic main street of the City of Anna Maria, running from Gulf to bay across the island’s northern tip. It is trolley-accessible and lined with independent shops, cafes, and restaurants including North Shore Cafe, J Burns Pizza, The Donut Experiment, and Poppo’s Taqueria. It gives Anna Maria city its distinct village character.
How are the schools on Anna Maria Island?
Anna Maria Elementary School serves the entire island and is in the top 10 percent of Florida elementary schools for test scores, with math and reading proficiency in the top 5 percent. It hosts the Guy Harvey Academy of Arts and Sciences and has a 14:1 student-teacher ratio. For a beach community school, the academic performance is exceptional.
Is Anna Maria Island in a flood zone?
Yes — the entire City of Anna Maria is in the 100-year floodplain within a Special Flood Hazard Area. Flood insurance is required for all mortgaged properties. The island is entirely within coastal high-hazard area designations. This is a fundamental characteristic of owning on Anna Maria Island, not an exception for certain properties.
How far is Anna Maria from Tampa?
Approximately 60 to 75 minutes from downtown Tampa in normal traffic via I-275 south across the Sunshine Skyway or via US-41/SR-64 through Bradenton. The drive involves crossing the Sunshine Skyway Bridge or the Bradenton surface road network, and peak season traffic can extend this significantly. Anna Maria Island is a Gulf Coast destination that is meaningfully removed from Tampa’s daily commute orbit.
How does Anna Maria compare to Holmes Beach and Bradenton Beach?
Anna Maria city is at the north tip with the most residential, community-oriented character and the highest median home price ($2.79M). Holmes Beach in the middle has Manatee Beach, the island’s best public beach infrastructure, and the most developed restaurant scene at a lower median ($1.35M). Bradenton Beach at the south end has the Historic Bridge Street district, the most tourist-oriented energy, and the most accessible price range. All three allow the Island Trolley and are connected for day-to-day island life.
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