Vacation Rentals in Anna Maria Island

Vacation Rentals in Anna Maria Island

Start comparing over 299 rentals in Anna Maria Island and book at the best price!

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Vacation house
Vacation apartment
Pool
Internet
Pets allowed
4.0
 & higher
Free cancellation

Vacation Rentals in Anna Maria Island

Vacation rental for 5 people, with lake view and yard as well as pool in Anna Maria Island
Vacation rental for 5 people, with lake view and yard as well as pool
2 bedrooms70yd to the beach
4.9
(21 reviews)
from $169 / nightFREE cancellation
Vacation rental for 6 people, with pool and lake view as well as balcony/terrace in Anna Maria Island
Vacation rental for 6 people, with pool and lake view as well as balcony/terrace
2 bedrooms200yd to the beach
4.9
(30 reviews)
from $142 / nightFREE cancellation
Vacation rental for 4 people, with pool in Anna Maria Island
Vacation rental for 4 people, with pool
2 bedrooms400yd to the beach
4.5
(20 reviews)
from $171 / night
Vacation rental for 6 people, with pool and balcony in Anna Maria Island
Vacation rental for 6 people, with pool and balcony
3 bedrooms20yd to the beach
4.9
(20 reviews)
from $225 / night

Popular Vacation Rentals in Anna Maria Island

Vacation rental for 6 people, with lake view and pool as well as yard in Anna Maria Island
Vacation rental for 6 people, with lake view and pool as well as yard
2 bedrooms200yd to the beach
4.7
(21 reviews)
from $142 / nightFREE cancellation
Vacation rental for 6 people, with pool, with pets in Anna Maria Island
Vacation rental for 6 people, with pool, with pets
2 bedrooms550yd to the beach
3.5
(7 reviews)
from $125 / nightFREE cancellation
Vacation rental for 6 people, with pool in Anna Maria Island
Vacation rental for 6 people, with pool
2 bedrooms150yd to the beach
4.3
(20 reviews)
from $138 / night
Vacation rental for 6 people, with pool and balcony in Anna Maria Island
Vacation rental for 6 people, with pool and balcony
3 bedrooms500yd to the beach
4.0
(13 reviews)
from $224 / night

Vacation rentals with free cancellation

Vacation rental for 10 people, with pool and yard in Anna Maria Island
Vacation rental for 10 people, with pool and yard
5 bedrooms200yd to the beach
5.0
(20 reviews)
from $368 / nightFREE cancellation
Vacation rental for 6 people, with pool and lake view as well as balcony/terrace in Anna Maria Island
Vacation rental for 6 people, with pool and lake view as well as balcony/terrace
2 bedrooms250yd to the beach
4.7
(24 reviews)
from $142 / nightFREE cancellation
Vacation rental for 8 people, with balcony and pool in Anna Maria Island
Vacation rental for 8 people, with balcony and pool
4 bedrooms450yd to the beach
4.8
(16 reviews)
from $182 / nightFREE cancellation
Vacation rental for 8 people, with lake view and yard as well as pool in Anna Maria Island
Vacation rental for 8 people, with lake view and yard as well as pool
4 bedrooms150yd to the beach
4.1
(21 reviews)
from $444 / nightFREE cancellation

Pet-friendly Vacation Rentals

Vacation rental for 3 people, with terrace and pool, kid friendly in Anna Maria Island
Pet allowed
Vacation rental for 3 people, with terrace and pool, kid friendly
1 bedroom60yd to the beach
4.2
(183 reviews)
from $179 / night
Vacation rental for 6 people, with pets in Anna Maria Island
Pet allowed
Vacation rental for 6 people, with pets
2 bedrooms200yd to the beach
5.0
(14 reviews)
from $177 / nightFREE cancellation
Vacation rental for 6 people in Anna Maria Island
Pet allowed
Vacation rental for 6 people
2 bedrooms200yd to the beach
4.1
(29 reviews)
from $250 / night
Vacation rental for 6 people, with pool in Anna Maria Island
Pet allowed
Vacation rental for 6 people, with pool
2 bedrooms150yd to the beach
4.8
(20 reviews)
from $229 / night

Vacation Rentals with Pool

Vacation rental for 6 people, with balcony and pool in Anna Maria Island
Pool
Vacation rental for 6 people, with balcony and pool
3 bedrooms20yd to the beach
4.7
(17 reviews)
from $222 / nightFREE cancellation
Vacation rental for 7 people, with ocean view and yard as well as pool in Anna Maria Island
Pool
Vacation rental for 7 people, with ocean view and yard as well as pool
3 bedrooms400yd to the beach
4.9
(20 reviews)
from $672 / night
Vacation rental for 6 people, with pool and yard in Anna Maria Island
Pool
Vacation rental for 6 people, with pool and yard
3 bedrooms90yd to the beach
4.6
(20 reviews)
from $172 / nightFREE cancellation
Condo for 6 people, with pool in Anna Maria Island
Pool
Condo for 6 people, with pool
2 bedrooms150yd to the beach
4.9
(15 reviews)
from $165 / nightFREE cancellation

Vacation Rentals with Internet

Condo for 4 people in Anna Maria Island
Internet
Condo for 4 people
2 bedrooms150yd to the beach
from $155 / nightFREE cancellation
Vacation rental for 12 people, with balcony and pool in Anna Maria Island
Internet
Vacation rental for 12 people, with balcony and pool
4 bedrooms250yd to the beach
4.7
(20 reviews)
from $628 / nightFREE cancellation
Vacation rental for 6 people, with pool in Anna Maria Island
Internet
Vacation rental for 6 people, with pool
2 bedrooms400yd to the beach
4.8
(24 reviews)
from $209 / nightFREE cancellation
Vacation rental for 6 people in Anna Maria Island
Internet
Vacation rental for 6 people
2 bedrooms100yd to the beach
4.9
(15 reviews)
from $199 / nightFREE cancellation

Find Vacation Rentals in Anna Maria Island

Map

Highlights Anna Maria Island

  • Beautiful beaches
  • Water sports
  • Regular festivals
  • Convenient transport
  • Seafood

Best vacation rentals in Anna Maria Island

Guests agree: these stays are highly rated for location, cleanliness, and more.
more...
Holmes Beach, Anna Maria Island
Vacation Rental • 6 Guests • 2 Bedrooms
4.8
(24 reviews)
Steps away from the "Beach Paradise 5" you’ll find the West Coast Surf Shop that has been in business for 99+ years and is stocked with beach apparel and supplies. The legendary "Skinny’s Place" is right across the street, serving up ice cold mugs of beer and the best burger on the beach. Just around the corner is the Island Centre Shopping which serves all of your shopping needs including eleven eateries, specialty shops, grocery, liquor store and other island conveniences. Hop on the free Island Trolley to explore other areas of the island. Many Florida attractions, such as Disney World, ...
from $189 / night
more...
Bradenton Beach, Anna Maria Island
Vacation Rental • 6 Guests • 2 Bedrooms
4.7
(24 reviews)
The first bedroom has a queen bed, glider rocker, cable TV, large walk-in closet with extra supplies, and an attached full bathroom. The second bedroom has a queen bed, twin bed, TV/monitor, and a large walk-in closet where guests will find plenty of gear for the beach. Another full bathroom is located adjacent to the second bedroom. The living room offers a comfy sleeper sofa, an oversized chair, and a large flatscreen cable TV. The dining room has a table, chairs, and bar stools at the counter providing plenty of room for a family meal or game night fun. The fully-equipped kitchen has eve...
from $142 / night
more...
Bradenton Beach, Anna Maria Island
Vacation Rental • 6 Guests • 2 Bedrooms
4.7
(16 reviews)
The Anna Maria Island Bridge Port Beach Resort is a beautiful 2 bedroom, 2 bathroom condo located 100 yards from the beautiful white sand beach of Anna Maria Island. The Bridge Port Beach Resort provides views of both the Gulf of Mexico and Florida's Intra-Coastal Waterway. The heated pool is just steps away from the front door. Bed Configuration: -Master bedroom - one king bed-Second bedroom - one queen bed-Living room - one queen sleeper sofa*With our continued desire to provide a superior guest experience we offer all our guests a professional linen service which includes freshly launder...
from $131 / night

Most popular in Anna Maria Island

Pool 1,906
Internet 1,040
Pets allowed 299
Balcony/Terrace 660
TV 1,038
Air conditioning 1,043

Prices and availability

Vacation rental prices Anna Maria Island

$443for 8 Oct - 15 Oct
$505 annual average
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Average price per week

Vacation rentals availability Anna Maria Island

16%for 8 Oct - 15 Oct
46% annual average
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Percentage of available rentals

Anna Maria Island Vacation Rentals

Find a Comfortable Beachfront Vacation Home

Anna Maria Island is crammed with beautiful vacation properties, including plenty of elegant 19th and early 20th century single-storey villas. These vacation rental properties are almost always within walking distance of the shore, have spacious yards, pools and room for a whole family to stretch out in their living areas.

Conveniently Located Vacation Apartments

Another feature of the island is its assortment of vacation apartments. All along Gulf Drive, from Bradenton Beach to Anna Maria, you’ll find apartment blocks and rental home options that have been divided into large holiday apartments. If you need an affordable, conveniently located spot, they could be ideal.

Vacationing on Anna Maria Island

One of Florida’s West Coast Gems

Anna Maria Island, FL is a barrier island located just off the west coast of Florida, just north of Sarasota and across Tampa Bay from St Petersburg. The island stretches for seven miles in total, and the coast is lined with soft, sandy beaches along the whole length.

An Easy to Navigate, Flat Sandy Island

Never more than two miles across, the whole island is served by handy trolley buses, and traveling between beaches is simple. Getting to Anna Maria Island, FL is almost as easy. Tampa Airport is just a few miles to the southeast, and has connections to all major US cities. There are regular shuttle buses from the airport to Anna Maria Island, as well as car rental services if you need your own vehicle.

One of America’s Best Places to Rent a Boat

While you can rent a car or 4x4 during your stay, it’s more fun to rent a sailing or powerboat during your stay. There are marinas with boat hire companies at Bradenton Bay and Bimini Bay, and you can hop between quays in your rental craft, seeing every inch of the island’s coast.

Aerial view of Anna Maria Island
Aerial view of Anna Maria Island

Activities

A Fantastic Fishing Destination

Anna Maria Island, FL is a superb place to test your fishing skills. Join a skipper at the port or rent your own boat and fish for Gulf species like mackerel, red snapper or redfish until the sun goes down.

A Great Destination for Beach Lovers

Both the east and west coasts of Anna Maria Island offer superb beaches, including Bradenton, Manatee, Holmes, Coquina and Cortez Beach. Sunbathe, snorkel in the emerald waters, play some volleyball and enjoy the endless sunshine.

A Popular Music and Arts Destination

Anna Maria Island has its cultural side, too. The Bradenton Blues Festival attracts huge names in December, while the waterfront in Anna Maria becomes a thriving arts venue when the Ringling International Arts Festival comes to town in October.

Anna Maria Island hosts an annual population of around 200 loggerhead turtles, who can travel 8,000 miles as part of their migratory routes.

Top 5 things to do in Anna Maria Island, FL

1. Spend the day at the beach

Public beaches like Coquina and Manatee have large parking lots, beautifully soft, warm sand, beautiful green waters, and enough space to enjoy whatever beach activities you desire.

2. Kayak in the mangroves

It’s not all about beaches on Anna Maria Island. You can also hire kayaks and paddle to Leffis Key and the mangrove tunnels in Robinson Preserve. Both are magical natural locations, and are full of birdlife, turtles and marine life.

3. Shop at the island’s vibrant markets

Shopping is a major activity on Anna Maria Island, and each beach seems to have its own market. One of the best places to head for craft bargains is Bradenton Beach’s Bridge Street Market (open on Saturdays), and you can shop for fine art at Bradenton’s Village of the Arts as well.

4. Dine al fresco on fresh Florida seafood

When you visit the Gulf, seafood is almost always high on the agenda, and Anna Maria Island doesn’t disappoint. Gastronomic highlights include Sandbar, the Beach Bistro and Sign of the Mermaid, but there’s no shortage of great spots.

5. Catch a sublime Anna Maria Island sunset

As the sun sets over the Gulf of Mexico, the view is incredible. Find a spot on the west coast of the island, grab a cocktail and enjoy the show. In summer, you may even have the chance to see turtle hatchlings make their way to the sea – another extraordinary spectacle.

Anna Maria City Pier
Anna Maria City Pier

Useful Information

Climate

Anna Maria Island has a sub-tropical climate, with temperatures averaging 75 degrees all year-round. They rarely dip far below that point, although sea temperatures rise considerably during the summer. Rainfall is moderate, but slightly higher in the summer (although it tends to be limited to afternoon showers).

Getting Around

Driving around the island is simple, with Gulf Drive running along its whole length. However, it makes sense to become acquainted with the trolley, which runs from early morning to 22:30 and stops every four blocks along a north-south route.

Festivals

Festivals are a big deal on the island. There are annual blues and arts events in Bradenton, as well as the Bayfest event in October, which has a classic rock theme. Cortez hosts an annual seafood festival, while January brings the Manatee County Fair. There’s always something going on.

FAQs: Vacation Rentals in Anna Maria Island

On average, how much do vacation rentals in Anna Maria Island cost?

Considering the average cost of $438 per night, Anna Maria Island lies at the upper end of the price range for vacation rentals in the USA.

When are vacation rentals cheaper in Anna Maria Island?

If you would like to save the maximum during your visit to Anna Maria Island, go there in October ($373 per night on average), September ($388), or November ($393), to find the lowest prices for the whole year.

When are vacation rentals more expensive in Anna Maria Island?

When it comes to looking for a vacation rental in Anna Maria Island, the months when you will pay the most are, in order of highest to lowest, March, February and July, with average prices per night of $552, $539, and $461, respectively.

Are there usually many vacation rentals available in Anna Maria Island?

When planning a vacation to Anna Maria Island, we recommend you to think ahead as 82% of rentals are usually booked, according to the data from last year.

What are the best months for a last-minute getaway?

The best months to find free accommodation in Anna Maria Island are May (the average amount of properties that are available reached 45% of the total last year), September (32%), and August (28%).

During which months is it more difficult to find available vacation rentals?

The accommodations in Anna Maria Island reach their peak in demand in March, with an availability rate of 0%. The second most requested month is February, with 0%, and the third is July with 5%. During this period, the availability is only 2%. It is therefore preferable to reserve early.

How many rentals does Holidu have in Anna Maria Island?

We have 860 properties for you in Anna Maria Island, provided by our 6 local and international partners.

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