Vacation Homes in Anna Maria Island
1,516 properties for Vacation Homes. Compare and book at the best price!
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Popular Vacation Homes in Anna Maria Island
Anna Maria (FL), Anna Maria Island
Vacation home for 12 people, with yard
from $645 per night
Holmes Beach, Anna Maria Island
Vacation home for 6 people, with balcony/terrace, with pets
Free cancellation
from $500 per night
Anna Maria (FL), Anna Maria Island
Vacation home for 8 people, with yard and pool as well as terrace
Free cancellation
from $599 per night
Holmes Beach, Anna Maria Island
9.6
Vacation home for 4 people, with terrace and yard
Free cancellation
from $439 per night
Holmes Beach, Anna Maria Island
9.9
Vacation home for 6 people, with yard, with pets
Free cancellation
from $500 per night
Bradenton Beach, Anna Maria Island
8.7
Vacation home for 18 people, with balcony and hot tub, with pets
Free cancellation
from $1,624 per night
Anna Maria (FL), Anna Maria Island
9.6
Vacation home for 6 people, with yard and balcony
Free cancellation
from $526 per night
Holmes Beach, Anna Maria Island
9.7
Vacation home for 2 people, with pool and terrace
Free cancellation
from $370 per night
Bradenton Beach, Anna Maria Island
9.0
Vacation home for 10 people, with balcony, with pets
Free cancellation
from $522 per night
Holmes Beach, Anna Maria Island
9.8
Vacation home for 2 people, with yard and balcony
from $381 per night
Holmes Beach, Anna Maria Island
9.8
Vacation home for 6 people, with yard
from $732 per night
Holmes Beach, Anna Maria Island
9.5
Vacation home for 2 people, with pool and terrace
Free cancellation
from $205 per night
Anna Maria (FL), Anna Maria Island
9.6
Vacation home for 6 people, with terrace and yard
Free cancellation
from $393 per night
Bradenton Beach, Anna Maria Island
9.7
Vacation home for 6 people, with pool and hot tub as well as balcony/terrace
Free cancellation
from $444 per night
Bradenton Beach, Anna Maria Island
9.6
Vacation home for 16 people, with hot tub and balcony
Free cancellation
from $1,514 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 $454 per night
Holmes Beach, Anna Maria Island
9.4
Vacation home for 2 people, with terrace and yard
Free cancellation
from $186 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 $499 per night
Anna Maria (FL), Anna Maria Island
9.6
Vacation home for 8 people, with yard, with pets
Free cancellation
from $441 per night
Holmes Beach, Anna Maria Island
9.8
Vacation home for 4 people, with hot tub and yard
Free cancellation
from $262 per night
Holmes Beach, Anna Maria Island
8.7
Vacation home for 6 people, with terrace, with pets
from $463 per night
Holmes Beach, Anna Maria Island
9.5
Vacation home for 6 people, with yard and terrace
Free cancellation
from $416 per night
Bradenton Beach, Anna Maria Island
9.8
Vacation home for 8 people, with hot tub and terrace, with pets
from $558 per night
Holmes Beach, Anna Maria Island
9.7
Vacation home for 6 people, with pool and balcony
Free cancellation
from $538 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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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 $343 / 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 $590 / night
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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 $541 / night
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