Vacation rentals in Anna Maria Island

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Top-rated vacation rentals in Anna Maria Island

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Home in Holmes Beach
Last Minute Availability! Gulf Views, 86° Pool/Spa
Amazing Location on Holmes beach, just steps to the water! Incredibly built home sets the highest standards of luxury living. It's the ideal retreat with expansive views of the outdoors from the moment you enter. Open concept and large sliders throughout creates the perfect indoor-outdoor lifestyle. Spend the day lounging in the resort-style heated pool w/spa, then enjoy drinks at sunset on the rooftop deck with wet bar, and breathtaking views of the Gulf of Mexico. Leaving this beauty is tough.
Aug. 20 – 27
$1,392 CAD per night
4.95 out of 5 average rating, 61 reviews
Guest favourite
Home in Anna Maria
My Private Beach
Remodeled one level waterfront home. Code supplied 3 days prior to arrival, no keys needed:) One level 4,571 sft home, heated pool on .8 acre, 120 ft wide waterfront private beach. 220 Tesla charger, one boat slip directly across street at no charge (last one on right) with a massive shared dock with lights for fishing, kayaking, boating. No SMOKING. Pack n Play. 2 Kayaks. Anna Maria law allows no backyard lights nor pool light as the turtles falsely think that is where they should nest.
Jan. 17 – 24
$1,789 CAD per night
4.96 out of 5 average rating, 52 reviews
Guest favourite
Home in Holmes Beach
True beach front home - 3 beds/2 bath, heated pool
This lovely 3 bedroom 2 bathroom home is situated on one of the most beautiful beaches imaginable; nestled among the sea oats leading out onto the white sand beaches and crystal clear waters this area is so famous for. As you cross the bridges and gaze at the glittering turquoise water fringed by swaying palms you will quickly realize that you have stepped back into old Florida – a slice of paradise that transports you back to a time when the pace of life was slower, gentler and more carefree.
Sep. 12 – 19
$1,132 CAD per night
4.95 out of 5 average rating, 37 reviews

Popular amenities for Anna Maria Island vacation rentals

Other great vacation rentals in Anna Maria Island

Guest favourite
Home in Anna Maria
Bean Pt. Bungalow - Half duplex w/private pool
Dec. 5 – 12
$632 CAD per night
4.88 out of 5 average rating, 34 reviews
Guest favourite
Home in Anna Maria
Manatee Harbour - heated pool, with canal access
Apr. 12 – 19
$737 CAD per night
5.0 out of 5 average rating, 73 reviews
Guest favourite
Home in Holmes Beach
Private Luxurious Ground Level Home
Sep. 20 – 27
$627 CAD per night
5.0 out of 5 average rating, 46 reviews
Guest favourite
Home in Anna Maria
Amie House Chef’s kitchen Fun pool - walk to beach
Nov. 16 – 23
$1,734 CAD per night
5.0 out of 5 average rating, 28 reviews
Guest favourite
Condo in Bradenton Beach
AMI Perfect Experience
Oct. 28 – Nov. 4
$265 CAD per night
5.0 out of 5 average rating, 15 reviews
Guest favourite
Home in Holmes Beach
Backyard Bliss Anna Maria Island
Nov. 8 – 15
$701 CAD per night
4.91 out of 5 average rating, 23 reviews
Guest favourite
Home in Holmes Beach
Luxury Home Steps to Quiet Beach on 78th St
Sep. 3 – 10
$539 CAD per night
5.0 out of 5 average rating, 34 reviews
Guest favourite
Condo in Holmes Beach
Lovely Beach View Condo on Anna Maria Island
Sep. 16 – 23
$359 CAD per night
5.0 out of 5 average rating, 22 reviews
Guest favourite
Home in Anna Maria
New Prof Decorated-Pool/Spa 5 minute walk 2 Ocean
Sep. 7 – 14
$1,230 CAD per night
5.0 out of 5 average rating, 57 reviews
Guest favourite
Condo in Holmes Beach
Bikini Bottom - Cabana, 40 steps to the sand!
Nov. 14 – 21
$348 CAD per night
4.98 out of 5 average rating, 51 reviews
Guest favourite
Home in Anna Maria
Island in the Sun
Jun. 25 – Jul. 2
$1,168 CAD per night
4.92 out of 5 average rating, 36 reviews
Guest favourite
Condo in Longboat Key
Beachfront Condo- Quiet & Secluded Private Beach
Dec. 9 – 16
$535 CAD per night
4.96 out of 5 average rating, 45 reviews

Destinations to explore