Trying to choose between Anna Maria Island, Siesta Key, and Longboat Key? You’re not alone. Each island offers a distinct lifestyle, beach experience, and housing mix, which can feel overwhelming if you’re exploring from out of state. In this guide, you’ll get a clear, side-by-side look at vibe, access, beaches, housing patterns, rules, and what to check on a tour. By the end, you’ll know which island fits your priorities and how to plan smart showings. Let’s dive in.

Where they sit and how to get there

Anna Maria Island sits in Manatee County and includes three municipalities at the north, middle, and south ends. The City of Anna Maria governs the northern tip, with Holmes Beach and Bradenton Beach to the south. Siesta Key is just southwest of downtown Sarasota in Sarasota County. Longboat Key stretches between Sarasota and Bradenton, governed by the Town of Longboat Key.

All three islands are drive-accessible via causeways. Seasonal traffic can be heavy during winter and holidays, and parking is limited near popular beaches and village areas. Typical drive time to Sarasota Bradenton International Airport ranges from about 20 to 40 minutes depending on location and time of day.

Public transit is limited on the islands. Plan to use a personal vehicle, rideshare, or bikes for short trips, and review municipal parking rules before touring.

Anna Maria Island: relaxed and village-like

Vibe and rhythm

If you want a slower pace and a walkable, small-town feel, Anna Maria Island stands out. The island is known for its “Old Florida” charm and family-run businesses, especially around Pine Avenue and village pockets. You’ll find a quieter, community-focused lifestyle that appeals to many second-home buyers and retirees. The Anna Maria Island Chamber is a helpful window into local dining and events.

Beaches and access

Beaches here are narrower than Siesta Key, with many low-key neighborhood access points. You’ll discover frequent public beach paths and parks along the island, often within walking distance of cottages and duplexes. Parking can be tight in peak times, so plan early beach outings.

Dining and daily life

Expect casual seafood spots, cafes, and local boutiques scattered from the City of Anna Maria to Bradenton Beach. Nightlife is modest compared with Siesta Key. This is a place where sundown beach walks and early dinners are the norm.

Homes you’ll see

You’ll tour older single-family cottages, duplexes, small condo buildings, and a growing number of newer elevated homes. Many properties have been renovated over time. Inland cottages can be more approachable in price, while direct Gulf-front homes and extensively remodeled properties command premiums.

Best fit if you value: a quiet vibe, walkability to low-rise shops and cafes, and a friendly, village feel.

Keep in mind: parking, short-term rental rules by municipality, and the age of structures when budgeting for updates.

Siesta Key: lively, amenity-rich beach life

Vibe and rhythm

Siesta Key is the most active of the three, especially around Siesta Village. You’ll find a wider mix of residents and visitors, more bars and restaurants, and a stronger seasonal buzz. It’s a good match if you want energy and walkable tourist amenities.

Beaches and access

Siesta’s Crescent Beach is famous for its wide shoreline and fine white quartz sand. Facilities at Siesta Key Beach include large parking areas, lifeguards, playgrounds, and concessions. This island is built for full beach days with amenities within reach.

Dining and daily life

You’ll have a broad choice of casual and mid-upscale dining, beach bars, and tourist shops concentrated in Siesta Village. Evenings are more vibrant here than on Anna Maria or Longboat Key.

Homes you’ll see

Expect a wide range: beachfront high- and mid-rise condos, garden-style complexes, smaller single-family homes, and luxury waterfront properties. Condo density is higher near village areas, and many condos have a short-term rental history. Beachfront units on Crescent Beach often command premium pricing.

Best fit if you value: a lively beach scene, walk-to-everything convenience, and robust amenities.

Keep in mind: seasonal traffic, condo association rules and fees, and verifying rental policies.

Longboat Key: private, resort-style living

Vibe and rhythm

Longboat Key is more upscale and low density, with an emphasis on privacy, golf, marinas, and resort services. It attracts buyers who want a controlled environment and quieter nights. The Town of Longboat Key oversees most services across the island.

Beaches and access

Much of the beachfront lines condo communities and resorts. Public beach accesses exist, but the feel is more private and serene, with fewer busy village zones than Siesta Key.

Dining and daily life

Dining leans more upscale and is often tied to resorts or private clubs. Nightlife is quieter, and boutique services cater to full-time residents and snowbirds.

Homes you’ll see

You’ll tour luxury beachfront condos, gated single-family communities, and resort residences. Many properties include amenities such as golf, marinas, and clubhouses. HOA and condo governance is common, which can be a plus if you want lock-and-leave convenience.

Best fit if you value: privacy, resort amenities, and an upscale, low-key atmosphere.

Keep in mind: HOA or club fees, rental limitations, and a quieter evening scene.

Rentals, rules, and utilities to verify

Short-term rental rules vary by municipality and can change. Anna Maria Island alone has multiple city governments, including the City of Anna Maria, each with its own ordinances. Siesta Key is under Sarasota County rules in most areas, and Longboat Key follows town regulations. Always confirm current licensing, minimum stays, occupancy limits, and tax requirements with the appropriate city or county before you buy.

Utilities also vary. Some neighborhoods are on public sewer, while others use private septic. Septic can impact renovation plans and maintenance costs. Review utility maps and service details with the county. Manatee buyers can start with Manatee County utilities, and Sarasota has similar resources for Siesta Key.

Flood, storms, and insurance planning

All three islands face hurricane winds and storm surge risk. Before you fall in love with a property, check its FEMA flood zone and Base Flood Elevation in the FEMA Flood Map Service Center. Review storm guidance and preparedness tips from the National Hurricane Center.

Insurance is a crucial line item. Florida coastal policies can change, and premiums vary by building features, elevation, and age. Review wind-mitigation features, ask for any elevation certificate, and get quotes early. For statewide insurance context and updates, use the Florida Office of Insurance Regulation.

Practical checklist:

• Ask for the most recent insurance premiums and any pending changes.
• Confirm roof age, impact windows or shutters, and attachment systems.
• For elevated homes, inspect pilings and structural elements for marine exposure.

Pricing and inventory patterns

Market conditions move fast. As a general pattern, inland or off-beach condos can begin in the lower to mid six-figure range depending on size and condition. Direct Gulf-front condos and larger single-family homes often run from the high six figures into multi-million ranges. For current local numbers, check reports from the Sarasota Association of REALTORS and review active listings with your agent.

Seasonality matters. Islands often see more listings and buyer activity in the fall and winter months, with tighter inventory in spring and summer.

Pre-tour homework

• List your top priorities: quiet vs lively, walkability, condo vs single-family, and whether rental income is essential.
• Confirm local short-term rental rules for any target property and whether a current license exists if income matters.
• Pull flood-zone data and lot elevation from FEMA and county records.
• Request HOA or condo documents and budgets ahead of time when possible.

On-island touring checklist

• Location and access: distance to beach access, parking options, guest rules, and whether beach frontage is public or private.
• Condition and maintenance: age of roof, HVAC, windows and doors, and evidence of salt corrosion.
• Septic vs sewer: location of tanks, service history, and any planned county conversions.
• Flooding and elevation: ask for elevation certificates and prior flood insurance information.
• Insurance and fees: obtain quotes and review HOA or condo reserves and assessment history.
• Neighborhood and seasonality: visit at different times to gauge traffic, noise, and rental turnover patterns.

Who to have on speed dial

• A local real estate agent experienced in coastal and island properties.
• A property inspector with coastal expertise.
• An insurance agent familiar with wind and flood policies.
• An HOA or condo manager for documents and budgets.
• A local lender used to coastal underwriting, elevation, and insurance requirements.

Which island fits you?

• Anna Maria Island: cottage charm, village energy at an easy pace, frequent public beach access points, and a friendly, downshifted lifestyle.
• Siesta Key: big-beach amenities, quartz-sand shores, and the most active dining and nightlife.
• Longboat Key: privacy, resort-level amenities, and upscale condos and communities built for quiet enjoyment.

If you want to compare these islands with confidence, partner with a local who knows both the coast and the nearby mainland options. For boutique guidance backed by national marketing reach, connect with Susan A Hill to plan a smart, efficient tour and narrow your shortlist.

FAQs

Which island has the best nightlife and dining?

• Siesta Key offers the most active evening scene and a dense cluster of restaurants and bars, while Anna Maria is more casual and Longboat Key is quieter and more upscale.

How long does it take to reach the airport from the islands?

• In typical conditions, plan about 20 to 40 minutes to Sarasota Bradenton International Airport, depending on island location and traffic.

Can I do short-term rentals on these islands?

• It depends on the municipality and your community’s rules; verify current ordinances and licensing with the city or county and confirm HOA or condo restrictions before assuming eligibility.

How big is the hurricane and flood risk on these islands?

• All three islands face hurricane and storm surge exposure; check any property’s flood zone and elevation on FEMA maps and factor insurance, mitigation features, and elevation into your decision.

Condo or single-family: which is better for low maintenance?

• Condos often include exterior maintenance and amenities through the association, while single-family homes offer more privacy and flexibility but may require more upkeep and individual insurance planning.

Are the beaches public or private?

• Each island has a mix; many areas provide public access points, and some beachfront is adjacent to private communities, so verify access easements and rules for any property you consider.