Vacation Rentals in Anna Maria Island

Vacation Rentals in Anna Maria Island

Start comparing over 872 rentals in Anna Maria Island and book at the best price!

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Vacation house
Vacation apartment
Pool
Internet
Balcony/Terrace
4.0
& higher
4.5
& higher

Best vacation rental deals in Anna Maria Island

9 nights
$4,772
$4,275
$475 / night
10% discount
Mon, 10/04 - Wed, 10/13
Vacation rental for 6 people, with balcony and pool
6 pers., 3 bedrooms, 500yd to the beach
4.8
(20 reviews)
12 nights
$5,869
$5,194
$432 / night
12% discount
Sun, 09/26 - Fri, 10/08
Vacation rental for 8 people, with balcony and pool
8 pers., 4 bedrooms, 500yd to the beach
5.0
(20 reviews)
7 nights
$4,227
$3,643
$520 / night
14% discount
Sun, 12/26 - Sun, 01/02
Vacation rental for 6 people, with pool and garden as well as ocean view and lake view
6 pers., 2 bedrooms, 70yd to the beach
FREE cancellation
4.5
(9 reviews)

Vacation rentals with free cancellation
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from
$457
per night

Vacation rental for 6 people, with pool and garden
6 pers., 3 bedrooms, 2,099ft², 150yd to the beach
FREE cancellation
4.9
(20 reviews)

from
$354
per night

Rental.type.detailed.condo for 6 people, with balcony
6 pers., 3 bedrooms, 20yd to the beach
FREE cancellation
4.6
(11 reviews)

from
$733
per night

Vacation rental for 12 people, with pool and garden
12 pers., 4 bedrooms, 2,799ft², 250yd to the beach
FREE cancellation
5.0
(20 reviews)
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Vacation Rentals in Anna Maria Island
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from
$143
per night

Vacation rental for 5 people, with garden and pool as well as lake view
5 pers., 2 bedrooms, 70yd to the beach
FREE cancellation
4.8
(22 reviews)

from
$155
per night

Vacation rental for 6 people, with lake view and pool as well as ocean view and garden
6 pers., 2 bedrooms, 200yd to the beach
FREE cancellation
4.9
(20 reviews)

from
$341
per night

Vacation rental for 6 people, with terrace, child-friendly
6 pers., 2 bedrooms, 150yd to the beach
FREE cancellation
4.6
(16 reviews)

from
$193
per night

Vacation rental for 3 people, with garden and view as well as pool
3 pers., 1 bedroom, 70yd to the beach
FREE cancellation
4.7
(38 reviews)

from
$473
per night

Vacation rental for 4 people, with lake view and pool as well as balcony
4 pers., 2 bedrooms, 90yd to the beach
FREE cancellation
4.4
(2 reviews)

from
$262
per night

Vacation rental for 4 people
4 pers., 2 bedrooms, 20yd to the beach
4.5
(21 reviews)

from
$473
per night

Vacation rental for 8 people, with lake view and garden as well as pool
8 pers., 4 bedrooms, 150yd to the beach
FREE cancellation
4.6
(21 reviews)

from
$142
per night

Vacation rental for 6 people, with lake view and balcony as well as pool and ocean view
6 pers., 2 bedrooms, 200yd to the beach
FREE cancellation
4.9
(30 reviews)

from
$142
per night

Vacation rental for 6 people
6 pers., 2 bedrooms, 70yd to the beach
FREE cancellation
4.7
(26 reviews)
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Pet-friendly Vacation Rentals
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from
$132
per night

Vacation rental for 2 people, with view and pool as well as garden, with pets
2 pers., 1 bedroom, 258ft², 70yd to the beach
4.5
(579 reviews)

from
$402
per night

Vacation rental for 8 people, with pool and balcony
8 pers., 4 bedrooms, 2,217ft², 500yd to the beach
FREE cancellation
4.6
(16 reviews)

from
$510
per night

Vacation rental for 10 people, with balcony and pool, with pets
10 pers., 5 bedrooms, 1,970ft², 200yd to the beach
FREE cancellation
4.4
(14 reviews)
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Vacation Rentals with Pool
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from
$142
per night

Vacation rental for 6 people
6 pers., 2 bedrooms, 250yd to the beach
FREE cancellation
4.4
(8 reviews)

from
$148
per night

Vacation rental for 6 people, with lake view and ocean view as well as pool and garden
6 pers., 2 bedrooms, 200yd to the beach
FREE cancellation
4.8
(10 reviews)

from
$148
per night

Vacation rental for 6 people, with pool and garden as well as lake view and ocean view
6 pers., 2 bedrooms, 200yd to the beach
FREE cancellation
4.8
(22 reviews)
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Vacation Rentals with Internet
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from
$278
per night

Vacation rental for 8 people
8 pers., 3 bedrooms, 80yd to the beach

from
$264
per night

Rental.type.detailed.condo for 4 people, with pool
4 pers., 2 bedrooms, 560ft², 100yd to the beach
FREE cancellation
5.0
(2 reviews)

from
$286
per night

Rental.type.detailed.condo for 8 people, with balcony and pool
8 pers., 3 bedrooms, 1,636ft², 150yd to the beach
FREE cancellation
5.0
(15 reviews)
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Find Vacation Rentals in Anna Maria Island

Map

Highlights Anna Maria Island

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

Most popular in Anna Maria Island

Pool 127
Internet 147
Balcony/Terrace 102
TV 149
Air conditioning 147
Parking 147

Prices and availability

Prices

October
November
December
January
February
$544
Sep 18 - Sep 25
$386 per night
Sep 25 - Oct 02
$377 per night
Oct 02 - Oct 09
$363 per night
Oct 09 - Oct 16
$375 per night
Oct 16 - Oct 23
$373 per night
Oct 23 - Oct 30
$378 per night
Oct 30 - Nov 06
$381 per night
Nov 06 - Nov 13
$384 per night
Nov 13 - Nov 20
$387 per night
Nov 20 - Nov 27
$401 per night
Nov 27 - Dec 04
$415 per night
Dec 04 - Dec 11
$399 per night
Dec 11 - Dec 18
$415 per night
Dec 18 - Dec 25
$450 per night
Dec 25 - Jan 01
$475 per night
Jan 01 - Jan 08
$448 per night
Jan 08 - Jan 15
$410 per night
Jan 15 - Jan 22
$411 per night
Jan 22 - Jan 29
$436 per night
Jan 29 - Feb 05
$459 per night
Feb 05 - Feb 12
$470 per night
Feb 12 - Feb 19
$507 per night
Feb 19 - Feb 26
$532 per night
Feb 26 - Mar 05
$544 per night
Average price per week

Availabilities

October
November
December
January
February
56 %
Sep 18 - Sep 25
33 %
Sep 25 - Oct 02
33 %
Oct 02 - Oct 09
28 %
Oct 09 - Oct 16
24 %
Oct 16 - Oct 23
30 %
Oct 23 - Oct 30
41 %
Oct 30 - Nov 06
41 %
Nov 06 - Nov 13
38 %
Nov 13 - Nov 20
44 %
Nov 20 - Nov 27
38 %
Nov 27 - Dec 04
52 %
Dec 04 - Dec 11
56 %
Dec 11 - Dec 18
56 %
Dec 18 - Dec 25
27 %
Dec 25 - Jan 01
13 %
Jan 01 - Jan 08
16 %
Jan 08 - Jan 15
40 %
Jan 15 - Jan 22
41 %
Jan 22 - Jan 29
35 %
Jan 29 - Feb 05
25 %
Feb 05 - Feb 12
15 %
Feb 12 - Feb 19
11 %
Feb 19 - Feb 26
7 %
Feb 26 - Mar 05
13 %
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

How much do you pay, on average, for vacation rentals in Anna Maria Island?

We can see from our data that Anna Maria Island has an average price of $405.91 per night, a relatively high one under the destinations in the USA.

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

After analyzing our data from last year, the months at the lowest possible cost in Anna Maria Island are October, November and May, with average prices of $307.03, $344.98, and $352.9, respectively.

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

Following the data observed in 2020, costs per night for accommodation here are usually higher, on average, during the months of February ($568.6), March ($559.38), and April ($468.58).

Should I plan a trip to Anna Maria Island well in advance?

You should book your stay well in advance when visiting Anna Maria Island, as only 17% of our accommodations are usually available throughout the year.

What time of the year can I find more free vacation rentals?

The months when it's the easiest to find free accommodation in Anna Maria Island are September (the average amount of properties that are free reached 31.25% of the total in 2020), December (29%), and April (25.25%).

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

The month with the highest average booked rental figures is February (only 1.2% of properties were available on average in 2020). Followed by March (5.75%), and June (7.25%).

Are there many rentals in Anna Maria Island?

We have 2900 properties for you in Anna Maria Island, provided by our 6 local and international partners.

Holidu compares hundreds of websites to find your perfect holiday rental for the best price.

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