Contemporary vacation home lit at dusk, with palms, sun loungers and a lit pool
Florida · South Central Gulf Coast

Anna Maria Island
vacation rentals

A seven-mile barrier island on Florida's Gulf Coast: soft white sand, warm Gulf water and the classic Old Florida character of three distinct communities.

2,224 homes listed 388 beachfront Up to 11 bedrooms Sleeps up to 30
2,224Homes listed
388Beachfront
1,413Houses & villas
807Condos
The island, in short

Luxury Anna Maria Island vacation rentals

Emerald Kite's Anna Maria Island vacation rentals cover the City of Anna Maria, Holmes Beach and Bradenton Beach. The Anna Maria Island beach rental collection includes privately owned beach houses, villas and condos, each represented by an established professional property manager. That range lets couples, families and larger groups compare different layouts without losing the local support that matters during a stay.

For guests seeking a higher-end stay, select luxury Anna Maria Island vacation homes pair generous living space with upgraded interiors, Gulf views or outdoor amenities. Some Anna Maria Island rentals have private pools; others trade private outdoor space for direct or walkable beach access. Condos can be a strong choice for travellers who prefer a beachfront position, elevators or shared resort-style amenities.

Location should guide the shortlist. Anna Maria rentals at the north end feel residential and put Pine Avenue and Bean Point close by. Holmes Beach vacation rentals offer a central base near shops, restaurants and Manatee Beach. Bradenton Beach suits visitors who want a livelier beach-town setting near restaurants, shops, waterfront activities and Coquina Beach. Use bedroom and guest filters together when planning a large-group or multigenerational trip.

Beachfront Villas & houses Condos Pet-friendly
2,224homes listed on Anna Maria Island
Marni - Emerald Kite destination agent
Your destination specialist

Speak to Marni

Marni looks after Anna Maria Island & Holmes Beach for Emerald Kite. Lines are open 7 days a week, 9 a.m. to 10 p.m. EST.

Find the right fit

Explore Anna Maria Island & Holmes Beach vacation rentals by size & style

Start with the space your group needs, then use the available property and experience links to narrow the collection. Each direct link opens matching Anna Maria Island & Holmes Beach vacation rentals, with the closest bedroom and guest-capacity matches shown first.

Handpicked in Anna Maria Island & Holmes Beach

Anna Maria Island beach houses, villas and condos

A rotating selection of professionally managed Anna Maria rentals across all three island communities. Compare bedrooms, bathrooms, sleeping capacity and rates, then explore the size links for more family and large-group options.

Search all 2,224 homes →
Three towns, one island

Anna Maria Island & Holmes Beach vacation rentals

The three communities offer different settings for beach rentals, so choosing the right part of the island is the quickest way to narrow your search.

North end

Anna Maria vacation rentals

Relaxed and residential, known for its beaches, wildlife and historic character. Pine Avenue is the best-known stretch for shopping, dining and strolling, and Bean Point at the tip has a peaceful setting and beautiful views.

Centre

Holmes Beach vacation rentals

The largest of the three communities and the island's commercial centre, with convenient access to beaches, restaurants, shops and rentals. Manatee Beach here is a family-friendly beach with convenient amenities.

South end

Bradenton Beach vacation homes

A distinctly beach-town atmosphere, with restaurants, shops, waterfront activities and access to the Gulf beaches. Coquina Beach at this end has picnic areas and visitor facilities.

On the island

Ways to spend the week

The Gulf beaches

Miles of shoreline for swimming, walking, shelling, sun and sunsets - Bean Point in the north, Manatee Beach in Holmes Beach and Coquina Beach in the south.

On the water

Boating, fishing, kayaking, paddleboarding, cycling, dolphin-watching excursions and nature, on an island the water runs through.

Fresh Gulf seafood

The island is best known for fresh local seafood. The Beach Bistro, 6600 Gulf Drive in Holmes Beach, has been honoured by ZAGAT, Wine Spectator and the James Beard Foundation.

Locally owned shops

Boutiques, gift, beach, clothing, art and jewelry stores, with Pine Avenue in Anna Maria the best-known stretch. Publix at 3900 East Bay Drive, Holmes Beach, covers the groceries.

Cycling and the trolley

Bicycles are a popular way to explore, and the free Anna Maria Island trolley connects all three communities, so many guests do without a rental car altogether.

Shelling and wildlife

Shelling, nature and quiet stretches of sand. The island takes protection of its beaches seriously, and visitors are asked to look after sea turtles and nesting birds.

Good to know

Getting there, getting around

Which airport

Sarasota-Bradenton International is 15 miles away and Tampa International is 51 miles. Sarasota is closer; Tampa has a wider variety of air carriers.

Getting around the island

You do not necessarily need to drive everywhere. The free Anna Maria Island trolley connects the three communities, bicycles are popular, and walking works well when your rental is close to the beach, restaurants or shops.

Rules on the beach

Beach regulations include restrictions on pets, alcohol, glass containers, bicycles and motorised vehicles, and visitors are asked to protect sea turtles, nesting birds and other wildlife. The Anna Maria Island Chamber of Commerce is a useful local resource.

House or condo?

A private house may offer more outdoor space, a private pool and separation between generations. A condo may offer a beachfront position or shared amenities. Both are worth comparing here before you decide.

Why book with us

Booking Anna Maria Island with Emerald Kite

Every home on this page is privately owned and run by an established local management company, and the agent you speak to knows the island.

  • Privately owned homes, each represented by an established management company
  • Vetted on location, quality, amenities and the manager’s responsiveness — and removed if that slips
  • A destination specialist helps compare the homes that fit your trip
  • Payment, cancellation and check-in terms supplied before you book
  • Villa Specialists available by phone
  • A complimentary concierge service for dining, activities and directions
How we work
Guest stories

What guests wrote after staying in Anna Maria Island & Holmes Beach

Unedited notes sent to the Emerald Kite team after their stay.

“Hi Madeline - Hope this email reaches you. The Travelling teachers group sends their grateful thanks to you for finding this superior residence in Anna Maria. The Property was located in a very convenient location. The house amenities wee up to date and the...”

Anna Maria Island & Holmes BeachFebruary 2025

“Our stay at Anna Maria property 896635 in December 2019 was fantastic. The location is perfect, right on the beautiful Anna Maria beach, so walks and runs on the beach are right out the back door. And the pool was perfect for our family of 16 - 8 adults and...”

Anna Maria Island & Holmes BeachJanuary 2020

“Good morning Neil, The Condo was fantastic for both my brother and his wife and my family. We truly enjoyed our stay, thank you. Everything about AMI was great too. The seafood and music scene was amazing people and weather. Can't wait to visit again....”

Anna Maria Island & Holmes BeachDecember 2019
Good to know

Anna Maria Island & Holmes Beach vacation rental questions

The things travellers ask us most before they book.

Where on Anna Maria Island should we stay?

It depends on the kind of week you want. Anna Maria at the northern end is relaxed and residential, known for its beaches, wildlife and historic character, with Pine Avenue for shopping and dining. Holmes Beach in the centre is the largest of the three communities and the island's commercial centre, which makes it particularly popular with families. Bradenton Beach at the southern end has a beach-town atmosphere, with restaurants, shops and waterfront activities.

Which beach should we head for?

Bean Point at the northern end is known for its peaceful setting and beautiful views. Manatee Beach in Holmes Beach is a popular family-friendly beach with convenient amenities. Coquina Beach at the southern end has picnic areas and visitor facilities. The island is seven miles long, so none of them is far.

Do we need a car on Anna Maria Island?

Not necessarily. The free Anna Maria Island trolley connects the island's three communities, which makes it convenient to reach beaches, restaurants and shopping without driving. Bicycles are also a popular way to explore, and walking works well if your rental is close to the beach or the shops. A car helps if you plan to travel off the island.

Are there rules on the beach we should know about?

Yes. Beach regulations include restrictions on pets, alcohol, glass containers, bicycles and motorised vehicles on the beach, and visitors are asked to protect sea turtles, nesting birds and other wildlife. The Anna Maria Island Chamber of Commerce publishes current local visitor information.

Where do we fly into?

Sarasota-Bradenton International Airport is 15 miles from the island and Tampa International Airport is 51 miles. Sarasota is the closer of the two, while Tampa offers a wider variety of air carriers.

Are these Anna Maria Island & Holmes Beach homes professionally managed?

Yes. Every home is privately owned but represented by an established property-management company responsible for cleaning, maintenance and guest support during your stay. Before a property joins the portfolio it is assessed on location, the quality of the accommodation, access to amenities and the reputation and responsiveness of the management company, and it is removed if it stops meeting that standard.

Can we bring a dog?

It varies by property rather than by destination. Ask your agent to identify homes that currently accept pets, then confirm the type, number and size limits before booking. Property rules, including smoking policies, are supplied for the individual home.

How is my payment protected?

Payment schedules, cancellation terms and any protections vary by property manager and destination. Your agent will identify the contracting property manager and provide the applicable rental agreement and payment terms for review before you book.

What do Platinum, Gold and Silver mean on a listing?

They are our own rankings and they describe the interior furnishings only - not the price, the view or the location. A Platinum or Gold home can cost less than a Silver one in a better position. Rankings move up when a home is upgraded and down when it has not been refreshed in a while.

How much does a rental cost, and when do we check in?

Where a manager has supplied a starting rate you will see it on the listing; where they have not, rates are quoted on request because they change with season and length of stay. Check-in and checkout times vary by property and manager, and your agent will confirm both for the home you choose.

Not sure which end of the island suits you?

Tell us who is travelling and when, and a destination specialist will narrow the homes down to the handful that actually suit your group.

Talk with a Villa Specialist

When should we call you?

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