Vacation Homes in Anna Maria Island
1,516 properties for Vacation Homes. Compare and book at the best price!
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- Vacation Homes Anna Maria Island
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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 $1,036 per night
Holmes Beach, Anna Maria Island
Vacation home for 6 people, with balcony/terrace, with pets
Free cancellation
from $498 per night
Anna Maria (FL), Anna Maria Island
Vacation home for 8 people, with yard and terrace as well as pool
Free cancellation
from $411 per night
Holmes Beach, Anna Maria Island
9.6
Vacation home for 4 people, with yard and terrace
Free cancellation
from $434 per night
Holmes Beach, Anna Maria Island
9.7
Vacation home for 2 people, with terrace and pool
Free cancellation
from $349 per night
Holmes Beach, Anna Maria Island
9.5
Vacation home for 2 people, with terrace and pool
Free cancellation
from $253 per night
Holmes Beach, Anna Maria Island
9.6
Vacation home for 6 people, with terrace, with pets
Free cancellation
from $570 per night
Holmes Beach, Anna Maria Island
9.8
Vacation home for 2 people, with yard and balcony
from $310 per night
Bradenton Beach, Anna Maria Island
9.4
Vacation home for 6 people, with terrace
Free cancellation
from $438 per night
Holmes Beach, Anna Maria Island
9.4
Vacation home for 4 people, with pool and terrace
Free cancellation
from $673 per night
Holmes Beach, Anna Maria Island
9.9
Vacation home for 4 people, with terrace
from $291 per night
Holmes Beach, Anna Maria Island
9.4
Vacation home for 8 people, with balcony
Free cancellation
from $513 per night
Holmes Beach, Anna Maria Island
9.6
Vacation home for 6 people, with terrace and yard
from $390 per night
Holmes Beach, Anna Maria Island
9.8
Vacation home for 5 people, with terrace and pool
Free cancellation
from $298 per night
Holmes Beach, Anna Maria Island
10.0
Vacation home for 10 people, with hot tub and yard
Free cancellation
from $1,137 per night
Holmes Beach, Anna Maria Island
9.1
Vacation home for 4 people, with terrace
Free cancellation
from $204 per night
Holmes Beach, Anna Maria Island
9.2
Vacation home for 2 people, with balcony
Free cancellation
from $343 per night
Holmes Beach, Anna Maria Island
9.9
Vacation home for 4 people, with balcony
from $323 per night
Bradenton Beach, Anna Maria Island
9.9
Vacation home for 4 people, with terrace and yard, with pets
from $222 per night
Anna Maria (FL), Anna Maria Island
9.6
Vacation home for 2 people, with pool and terrace
from $290 per night
Holmes Beach, Anna Maria Island
9.8
Vacation home for 12 people, with balcony
Free cancellation
from $840 per night
Bradenton Beach, Anna Maria Island
9.9
Vacation home for 4 people, with balcony
Free cancellation
from $285 per night
Holmes Beach, Anna Maria Island
9.2
Vacation home for 6 people, with yard and hot tub, with pets
from $418 per night
Holmes Beach, Anna Maria Island
9.6
Vacation home for 6 people, with terrace
Free cancellation
from $391 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 • 893 ft² • 2 Bedrooms
Anna Maria (FL), Anna Maria Island
9.9
The Ballyhoo is a ground floor cottage located on Bean Point at the very tip of Anna Maria Island. Around the corner, (200 feet away) is the Rod and Reel Pier and beach. A classic 1940s old Florida fishing pier. The pier is an excellent place to see all our local wildlife, dolphins, herons, pelicans, and if you are lucky, maybe a manatee. The pier offers some of the best fishing on the island. A family friendly place with very good food and drink. With panoramic views of Tampa Bay, the Skyway, Egmont Key and civil war era lighthouse, it's not to be missed. Take one our provided bikes or wal...
from $292 / night
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Holmes Beach, Anna Maria Island
Vacation Home • 797 ft² • 2 Bedrooms
Holmes Beach, Anna Maria Island
9.5
The cozy front porch of Gulf Winds A invites you to have your morning coffee or your evening cocktail and in the back yard you can enjoy your dinner and make use of the gas grill. A huge table umbrella provides you with shade if needed. The two bedroom two bath unit is located on a very quiet street. The Master bedroom has a king size bed and the guest bedroom has a queen. The home has been totally remodeled, everything is new from furniture to floors and appliances. There are TV's in the master bedroom and the living room, and of course there is free WiFi. Everything you need to enjoy your...
from $331 / night
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Anna Maria (FL), Anna Maria Island
Vacation Home • 1098 ft² • 2 Bedrooms
Anna Maria (FL), Anna Maria Island
9.5
Welcome to Sea Breeze, our newly renovated home with 2 bedrooms / 2 bathrooms, a private dock, and an unobstructed, natural view of Bimini Bay. Smart TV, WiFi, free access to Netflix, washer/dryer, and a full kitchen with cooking essentials. Sea Breeze cottage is located at the North End of Anna Maria Island, sailboat direct to Bimini Bay, walking distance to Pine Ave, City Pier, and popular restaurants. Our private oasis has everything needed for a perfect beach vacation at the serene North End of Anna Maria Island. The entire wall of floor-to-ceiling windows frames the bay view inside the...
from $431 / night
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