Vacation Rentals on Anna Maria Island

Start comparing over 7,244 rentals in Anna Maria Island and book at the best price!

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Best vacation rental deals in Anna Maria Island

Sat, 01/02 - Sat, 01/09
Vacation house for 4 people, with terrace
4 pers., 2 bedrooms, 893ft², 300yd to the beach
5.0
4 reviews

7 nights
$1,953

$2,146-9%
Sat, 01/02 - Sat, 01/09
Apartment for 5 people
5 pers., 2 bedrooms, 710ft², 70yd to the beach
4.6
22 reviews

7 nights
$1,608

$1,710-6%
Sat, 01/02 - Sat, 01/09
Vacation house for 2 people, with terrace
2 pers., 1 bedroom, 592ft², 300yd to the beach
4.5
7 reviews

7 nights
$1,436

$1,535-6%

Vacation Rentals in Anna Maria Island

Apartment for 5 people, child-friendly
5 pers., 2 bedrooms, 100yd to the beach
4.4
20 reviews
Anna Maria Island, Southwest Florida

from
$99
per night

Vacation house for 18 people, with garden
18 pers., 8 bedrooms, 0.6mi to the beach
Anna Maria (FL), Anna Maria Island

from
$858
per night

Villa for 6 people, with terrace
6 pers., 2 bedrooms, 90yd to the beach
3.8
2 reviews
Bradenton Beach, Anna Maria Island

from
$179
per night

Vacation house for 8 people, with pool
8 pers., 4 bedrooms, 500yd to the beach
Holmes Beach, Anna Maria Island

from
$558
per night

Vacation house for 8 people, with pool and jacuzzi as well as terrace, child-friendly
8 pers., 4 bedrooms, 700yd to the beach
Anna Maria (FL), Anna Maria Island

from
$657
per night

Vacation house for 23 people, with pool and garden
23 pers., 9 bedrooms, 200yd to the beach
Bradenton Beach, Anna Maria Island

from
$625
per night

Vacation house for 6 people
6 pers., 3 bedrooms, 90yd to the beach
Holmes Beach, Anna Maria Island

from
$309
per night

Vacation house for 8 people, with pool
8 pers., 4 bedrooms, 50yd to the beach
Holmes Beach, Anna Maria Island

from
$498
per night

Vacation house for 8 people, with terrace
8 pers., 4 bedrooms, 200yd to the beach
Anna Maria (FL), Anna Maria Island

from
$205
per night

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Pet-friendly Vacation Rentals

Vacation house for 14 people, with pool and balcony, child-friendly
14 pers., 4 bedrooms, 3,197ft², 300yd to the beach,
4.7
20 reviews
Anna Maria (FL), Anna Maria Island

from
$547
per night

Vacation house for 8 people, with pets
8 pers., 4 bedrooms, 400yd to the beach,
Holmes Beach, Anna Maria Island

from
$595
per night

Vacation house for 11 people, with garden
11 pers., 5 bedrooms, 250yd to the beach,
Anna Maria (FL), Anna Maria Island

from
$381
per night

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Vacation Rentals with Pool

Vacation house for 8 people, with pool and terrace as well as jacuzzi
8 pers., 3 bedrooms, 1,335ft², 250yd to the beach
4.6
9 reviews
Anna Maria (FL), Anna Maria Island

from
$142
per night

Villa for 6 people, child-friendly
6 pers., 2 bedrooms, 100yd to the beach
Holmes Beach, Anna Maria Island

from
$144
per night

Vacation house for 6 people, with pool
6 pers., 3 bedrooms, 1,733ft², 70yd to the beach
Bradenton Beach, Anna Maria Island

from
$266
per night

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Vacation Rentals with Internet

Vacation house for 6 people
6 pers., 3 bedrooms, 300yd to the beach
Holmes Beach, Anna Maria Island

from
$444
per night

Vacation house for 6 people
6 pers., 2 bedrooms, 200yd to the beach
4.4
3 reviews
Bradenton Beach, Anna Maria Island

from
$145
per night

Villa for 6 people, with terrace
6 pers., 1 bedroom, 700yd to the beach
Holmes Beach, Anna Maria Island

from
$120
per night

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Highlights Anna Maria Island

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

Most popular in Anna Maria Island

Pool 1,620
Internet 2,058
Balcony/Terrace 1,659
TV 1,804
Air conditioning 1,977
Parking 1,785
Washing machine 1,817
Jacuzzi 420
Heating 1,472

Prices and availability

Prices

December
January
February
March
April
May
$526
Nov 21 - Nov 28
$351 per night
Nov 28 - Dec 05
$376 per night
Dec 05 - Dec 12
$349 per night
Dec 12 - Dec 19
$356 per night
Dec 19 - Dec 26
$407 per night
Dec 26 - Jan 02
$453 per night
Jan 02 - Jan 09
$428 per night
Jan 09 - Jan 16
$378 per night
Jan 16 - Jan 23
$386 per night
Jan 23 - Jan 30
$393 per night
Jan 30 - Feb 06
$409 per night
Feb 06 - Feb 13
$456 per night
Feb 13 - Feb 20
$488 per night
Feb 20 - Feb 27
$503 per night
Feb 27 - Mar 06
$522 per night
Mar 06 - Mar 13
$526 per night
Mar 13 - Mar 20
$522 per night
Mar 20 - Mar 27
$513 per night
Mar 27 - Apr 03
$521 per night
Apr 03 - Apr 10
$517 per night
Apr 10 - Apr 17
$453 per night
Apr 17 - Apr 24
$397 per night
Apr 24 - May 01
$378 per night
May 01 - May 08
$389 per night
Average price per week

Availabilities

December
January
February
March
April
May
80 %
Nov 21 - Nov 28
27 %
Nov 28 - Dec 05
38 %
Dec 05 - Dec 12
64 %
Dec 12 - Dec 19
64 %
Dec 19 - Dec 26
50 %
Dec 26 - Jan 02
22 %
Jan 02 - Jan 09
42 %
Jan 09 - Jan 16
47 %
Jan 16 - Jan 23
37 %
Jan 23 - Jan 30
36 %
Jan 30 - Feb 06
22 %
Feb 06 - Feb 13
17 %
Feb 13 - Feb 20
21 %
Feb 20 - Feb 27
20 %
Feb 27 - Mar 06
21 %
Mar 06 - Mar 13
31 %
Mar 13 - Mar 20
34 %
Mar 20 - Mar 27
33 %
Mar 27 - Apr 03
37 %
Apr 03 - Apr 10
42 %
Apr 10 - Apr 17
65 %
Apr 17 - Apr 24
66 %
Apr 24 - May 01
75 %
May 01 - May 08
80 %
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

What is the average price for vacation rentals in Anna Maria Island?

Anna Maria Island is one of the destinations in the USA, which is the most expensive. The overnight stay there costs on average $322.98 per night.

During which months can you find the best price for vacation rentals in Anna Maria Island?

If you want to make the most of your money, the most budget-friendly months to visit Anna Maria Island are October ($259.23 the average per night for accommodation), November ($261.26), and September ($262.64).

When does the price of vacation rentals in Anna Maria Island go up the most?

In 2019, the month that offered the highest average prices in Anna Maria Island was February, with an average price of $471.04 per night. This was followed by March, with an average of $428.68, and April, with $359.38.

Is Anna Maria Island a good location for a last-minute getaway?

We recommend you to book in advance in Anna Maria Island as only 24% of the accommodations are available throughout the year, according to our 2019 data.

When are more vacation rentals available?

In 2019, the months with the most vacation rentals available of the year in Anna Maria Island were September, May and June, with average availabilities of 40.75%, 37.25%, and 37.2%, respectively.

Which months is it more difficult to find available vacation rentals??

According to data from 2019, the months when it is most difficult to find accommodation in Anna Maria Island are, in order, February (with 1.4% of available rentals), March (6.25%), and January (10%).

Are there many vacation rentals in Anna Maria Island?

Our inventory features around 2800 properties from 10 partners.

  1. Vacation rentals
  2. USA
  3. Florida
  4. Gulf Coast
  5. Anna Maria Island