Vacation Homes in Anna Maria Island
996 properties for Vacation Homes. Compare and book at the best price!
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Popular Vacation Homes in Anna Maria Island
Holmes Beach, Anna Maria Island
Vacation home for 6 people, with balcony/terrace, with pets
Free cancellation
from $502 per night
Anna Maria (FL), Anna Maria Island
Vacation home for 8 people, with terrace and pool as well as yard
Free cancellation
from $629 per night
Anna Maria (FL), Anna Maria Island
Vacation home for 12 people, with yard
from $1,031 per night
Holmes Beach, Anna Maria Island
9.6
Vacation home for 4 people, with terrace and yard
Free cancellation
from $502 per night
Holmes Beach, Anna Maria Island
9.9
Vacation home for 6 people, with yard, with pets
Free cancellation
from $498 per night
Bradenton Beach, Anna Maria Island
8.7
Vacation home for 18 people, with hot tub and balcony, with pets
Free cancellation
from $1,672 per night
Holmes Beach, Anna Maria Island
9.8
Vacation home for 6 people, with yard
from $764 per night
Holmes Beach, Anna Maria Island
9.7
Vacation home for 2 people, with pool and terrace
Free cancellation
from $395 per night
Bradenton Beach, Anna Maria Island
9.5
Vacation home for 16 people, with hot tub and balcony
Free cancellation
from $1,461 per night
Bradenton Beach, Anna Maria Island
9.9
Vacation home for 6 people, with hot tub and pool as well as balcony
Free cancellation
from $415 per night
Holmes Beach, Anna Maria Island
9.4
Vacation home for 2 people, with terrace and yard
Free cancellation
from $187 per night
Bradenton Beach, Anna Maria Island
9.0
Vacation home for 10 people, with balcony, with pets
Free cancellation
from $663 per night
Holmes Beach, Anna Maria Island
9.5
Vacation home for 2 people, with terrace and pool
Free cancellation
from $262 per night
Anna Maria (FL), Anna Maria Island
9.6
Vacation home for 6 people, with yard and balcony
Free cancellation
from $605 per night
Bradenton Beach, Anna Maria Island
9.7
Vacation home for 6 people, with balcony/terrace and pool as well as hot tub
Free cancellation
from $503 per night
Anna Maria (FL), Anna Maria Island
9.6
Vacation home for 8 people, with yard, with pets
Free cancellation
from $506 per night
Anna Maria (FL), Anna Maria Island
9.6
Vacation home for 6 people, with terrace and yard
Free cancellation
from $348 per night
Holmes Beach, Anna Maria Island
8.8
Vacation home for 6 people, with terrace, with pets
from $510 per night
Holmes Beach, Anna Maria Island
9.8
Vacation home for 2 people, with yard and balcony
from $379 per night
Anna Maria (FL), Anna Maria Island
9.9
Vacation home for 4 people, with hot tub and terrace, with pets
Free cancellation
from $625 per night
Holmes Beach, Anna Maria Island
9.4
Vacation home for 6 people, with yard and terrace
Free cancellation
from $374 per night
Bradenton Beach, Anna Maria Island
9.8
Vacation home for 8 people, with hot tub and terrace
from $615 per night
Holmes Beach, Anna Maria Island
9.7
Vacation home for 6 people, with balcony and pool
Free cancellation
from $567 per night
Holmes Beach, Anna Maria Island
9.3
Vacation home for 4 people, with terrace, with pets
Free cancellation
from $320 per night
Find Vacation Homes in Anna Maria Island
Best Vacation Homes in Anna Maria Island
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Anna Maria (FL), Anna Maria Island
Vacation Home • 1496 ft² • 2 Bedrooms
Anna Maria (FL), Anna Maria Island
9.9
Our vacation home is two blocks to either the Gulf of Mexico or Tampa Bay…Bean Point Beach! We have remodeled the entire house due to hurricanes. We have a heated pool with a table in the water to enjoy cocktails while you soak up the sun. Our home has an outdoor shower, kayaks and a charcoal and gas grill. We are located on a large corner lot and we are completely fenced in so your pet can enjoy our yard as well. Lanai: We have a screened in porch, near the pool with chairs, and TV. Our pets love to sit in the sun and watch the world go by... There is also a sitting area patio. Living Room...
from $566 / night
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Holmes Beach, Anna Maria Island
Vacation Home • 6 Guests • 2 Bedrooms
Holmes Beach, Anna Maria Island
9.9
Seabreeze Cottage is situated on a quiet road with access to the beach, via a leafy lane, just 200 feet away. The property, which is accessed via a set of exterior steps, is very well furnished and equipped offering everything we hope you would need to enjoy the perfect holiday. The master bedroom has a King size bed and benefits from an en-suite bathroom with bath with overhead shower, basin and WC. The 2nd bedroom has Twin beds which can be joined to make a King and the family bathroom has a shower, basin and WC. The sofa in the sitting room can also be made into a bed which allows the pr...
from $307 / night
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Holmes Beach, Anna Maria Island
Vacation Home • 3498 ft² • 4 Bedrooms
Holmes Beach, Anna Maria Island
9.6
VRC19-000271-0* Calendar does NOT reflect availability- --contact me for minimum requirement. VRBO website does NOT determine availability--ONLY owner does. Further Questions and/or request dates, contact me per email. Calendar is not posted for this reason. If I am contacted during a weekend, I can't respond until the following Monday. The rental charge December $13,000(plus tax),for January $13,000 (plus tax), February is $15,000 (plus tax) March, $15,000(plus tax) & April $15,000(plus tax). I still have April 2026 available- Easter is Sunday April 5th. Contact me for various months o...
from $615 / night
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Other holiday ideas and property types in Anna Maria Island that might be interesting
FAQs: Vacation Homes in Anna Maria Island
Which filters are the most searched for by travelers when organizing their vacation on Anna Maria Island?
According to Holidu, when travelers search for homes on Anna Maria Island, often they choose the following filters: pool (20%), internet (19%), and a air-conditioning (10%). Last year, the majority of travelers selected at least one of these options when finding the perfect home.
Which types of facilities can you typically find at the homes on Anna Maria Island?
In regards to the amenities you can find on Holidu, it seems that the homes on Anna Maria Island have everything that travelers wish for! Here, the homes generally include a variety of amenities, the most popular being: internet (80%), air-conditioning (75%), and pool (74%)...Are you convinced yet?
How are the homes generally rated on Anna Maria Island?
According to last year, only 12% of the homes on Anna Maria Island have a rating of 4.5 stars. It can therefore be assumed that it is not the best destination for the highest-rated homes in the USA.
Are the homes on Anna Maria Island child-friendly?
Judging by the Holidu database, 16% of homes on Anna Maria Island are child-friendly, so you won't struggle finding the ideal home for you and your children.
Are the homes on Anna Maria Island suitable for travelers who wish to take their pets on vacation?
For sure! On Anna Maria Island, 33% of the homes give you the opportunity to bring along your furry best friend, 17% also have a garden!
Do the homes on Anna Maria Island tend to offer an internet connection?
Certainly! Based on the last year, 80% of homes on Anna Maria Island offer Wi-Fi. This means that you will be able to stay connected throughout your stay!
What is the average price for homes on Anna Maria Island?
Many homes on Anna Maria Island are generally fairly expensive. According to Holidu, 27% are at more than $500 a night.
Do the homes on Anna Maria Island usually have a fireplace or a pool?
For sure! According to Holidu, 74% of homes on Anna Maria Island have a pool. It is the perfect destination for a long summer weekend! 72% even have a barbecue!
Are the homes on Anna Maria Island suitable for trips with a large group or better for an escape as a couple?
In Anna Maria Island, according to Holidu, 41% of homes are suitable for up to eight travelers, 33% of these homes contain at least four bedrooms. But 98% of homes are also perfect for families of up to four people, and 94% of the homes are made up of at least two separate bedrooms. Anna Maria Island is therefore the ideal destination for taking your family on vacation (small or large)!
For a luxury trip in Anna Maria Island, are Homes a good idea?
Some homes are, but others aren't as luxurious. So if you are looking for that special accommodation, don't delay in making a reservation because only 74% have a pool, while 75% have AC none have a sauna.
Do the homes in Anna Maria Island offer outdoor space to enjoy?
58% of homes have a balcony or terrace, and 18% have a view, but since it is not very common so availability can be limited. If this is important to you, you should anticipate a bit more time for research, and use the filters to be sure to find the home of your dreams. However, if you like to eat your meals in nature, and especially if you like barbecues,72% of the homes are equipped with them.