Family walking toward the sea on Anna Maria Island

Anna Maria Island Vacation Rentals

Anna Maria Island Vacation Rentals

Location
Find your place on the island

Beach days start with the right home.

A pool for the kids. A quiet patio for your morning coffee. Enough space for everyone to sit down together. Start with the things that will make this trip yours.

AnnaMariaRentals.com brings together Anna Maria Island vacation rentals managed by Florida Vacation Homes and homes managed by other professional local rental companies. Compare the properties, choose your dates and check the details that matter to your group.

A few places to begin

Bring family or friends together in a waterfront home with a private pool. Take a closer look at Happy Place and Island Life Villa.

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Happy Place vacation rental in Holmes Beach
Pool homes · Larger groups

Happy Place

Holmes Beach · 6 bedrooms · Up to 12 guests

A canalfront home with a private pool and a separate guest apartment. The beach is approximately 0.4 miles away.

30-night minimum

Explore this property
Island Life Villa vacation rental in Holmes Beach
Waterfront · Family gatherings

Island Life Villa

Holmes Beach · 5 bedrooms · Up to 10 guests

Two kitchens, room to spread out and a pool overlooking the water. The beach is approximately 0.2 miles away.

7-night minimum; seasonal arrival rules apply

Explore this property

Availability, minimum stays and amenities vary by property and travel dates. Check the current listing and rental terms before booking.

One island, three communities

Where should you stay on Anna Maria Island?

The address shapes your day. Think about the beach you’ll use, where you’d like to eat and how much driving you want to do.

Anna Maria Island area overviewAnna Maria is at the north end, Holmes Beach in the middle and Bradenton Beach at the south end. This is a schematic, not a street map.123Anna MariaHolmes BeachBradenton BeachGulfBayN

Island overview · not to scale

1Anna Maria

Look toward the north end if Pine Avenue’s shops and places to eat are part of your plans. Compare the exact address: a home near the bay offers a different beach routine from one near the Gulf.

Explore Anna Maria dining

2Holmes Beach

A central base for exploring the island, with Manatee Public Beach and everyday stops nearby. Check the walking route from each rental; “Holmes Beach” covers more than the few blocks around the beach entrance.

Explore Holmes Beach dining

3Bradenton Beach

Consider the south end if you’d like Bridge Street’s restaurants and shops within reach. Cortez Beach and Coquina Beach are also in this part of the island. Distance to each depends on your rental’s address.

Explore Bradenton Beach dining
Know who’s behind your stay

Local rental companies. Clearer choices.

Our collection includes properties managed by Florida Vacation Homes alongside rentals managed by other professional local companies. The company looking after your stay depends on the home you choose.

Compare the whole stay

Look beyond the bedroom count. Photos, floor plans where available, amenities and rental terms help you decide whether a property works for your group.

Ask before you book

Unsure about a pool, a beach route or the company managing a home? Contact our reservations team so you can clarify the details before making a booking.

Keep the right contact handy

Review the manager’s details and arrival instructions in your booking confirmation. Use the contact provided for that property when you need help during your stay.

Before you choose

Small details make a big difference.

A view isn’t beach access

Beachfront, beach view and near the beach describe different settings. Look for the actual beach entrance and walking route, including any roads you’ll cross with chairs and a cooler.

Know which water you’re on

A canalfront or bayfront home can be lovely for watching the water. It does not necessarily have a sandy beach. If you’re bringing a boat, confirm dock access, restrictions and suitability before booking.

Check the pool details

Is the pool private or shared? Is heating included, optional or seasonal? A spa may have separate operating rules. Confirm those details for your dates rather than relying on a photo.

Count beds, not just bedrooms

Check bed sizes, stairs and where everyone will sleep. A separate guest suite may suit two families, while a group with young children may prefer bedrooms together in the main home.

Good questions to ask

Planning your island stay

Which part of Anna Maria Island is right for our trip?

Start with what you want nearby. Anna Maria puts you toward Pine Avenue and the north end; Holmes Beach is a central base; Bradenton Beach puts you toward Bridge Street and the southern beaches. Then check each home’s precise location, beach access and route to the places you plan to visit.

Do you manage every property on AnnaMariaRentals.com?

No. We market homes managed by Florida Vacation Homes and homes managed by other professional local rental companies. Management, arrival arrangements and booking terms vary by property. Review the listing and rental agreement, and ask us to clarify the managing company if it is not clear before you book.

Are waterfront rentals always on the beach?

No. Waterfront can mean a bay or canal setting. Beachfront usually describes a location along the beach, while a beach view does not necessarily mean direct access. Check the property description and the route to a public beach entrance before deciding.

How can I tell whether a rental has a private or heated pool?

Read the amenities and pool information for the specific property. A shared community pool is different from a pool reserved for your home. Heating arrangements, extra charges and temperature expectations can vary, so confirm them for your travel dates before booking.

Can we bring a dog?

Pet policies are specific to each home, and many properties do not allow pets. Do not assume a rental accepts dogs unless the listing and rental terms confirm it. Ask about approval, size or number limits and any charges before making a reservation.

Can I book a short break, a week or a month?

Minimum stays vary. Some listings require seven nights; others require 30 nights, and seasonal arrival-day rules may apply. Enter your dates and check the individual property. For a condo, also look for association applications and any advance approval deadlines.

What should I check in the price and cancellation terms?

Review the full quoted total, including taxes, cleaning charges and any optional extras you select. Check the payment schedule, deposit requirements and cancellation terms in the agreement for your chosen property. These may differ between homes and managing companies.

Do we need a car for the whole stay?

That depends on your address and plans. Compare the walking route to the beach, restaurants and transport stops before deciding. Our island trolley and bus guide and bike and golf cart rental guide are useful starting points; check current services and rental rules when planning your trip.

Make yourself at home

Plan the days around your stay.

Leave room for a car-free day

Work out how you’ll get from your rental to the places you want to visit.

Trolley and bus guide

Find dinner close to home

Pick a few nearby options for the evenings when nobody feels like cooking.

Holmes Beach restaurants

Find Your Anna Maria Island Vacation Rental

Find a place to stay in Anna Maria, Holmes Beach or Bradenton Beach. Browse beachfront condos, waterfront homes and vacation homes with private pools, then compare availability for your dates. Check each listing for sleeping arrangements, pool details and distance to the beach so you can choose a rental that fits your group.

StunningBeaches

StunningOcean Water

StunningSunsets

Things To Do

Book with Florida Vacation Homes on Anna Maria Rentals .com

Professionally Managed

Guest support for a better experience

Effortless Booking

Availability Calendars are live & up to date for Instant Booking

Expert Planners

Call our vacation planners to book your vacation to Anna Maria Island

Everything You Need To Book A Vacation Rental & Plan Your Trip

Start with your dates and the number of guests, then compare the homes and condos available for your trip. Before booking, review the property’s amenities, total price, cancellation terms and check-in details.

Planning to explore without driving every day? Our island trolley and bus guide and bike and golf cart rental guide can help you plan how to get around.

beach walkway

Anna Maria Island Has so much to offer

Leave room in your plans for a beach morning, a shopping stop and dinner close to your rental. Browse Holmes Beach restaurants or Bradenton Beach restaurants to compare menus and settings.

Our Anna Maria Island shopping guide covers local shops and beach supplies. Check current hours and reservation policies with each business before heading out.

Your dates. Your kind of stay.

Find your Anna Maria Island vacation rental.

Start with your dates and guest count, then compare the homes and condos available for your trip.

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