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Search results; Over 1,000 homes in Anna Maria

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Superhost
Cottage in Anna Maria
Sea Wave-[BRAND NEW 2026] Waterfront Oasis
3 bedrooms, 3 beds, 2 private bathrooms
4–9 Oct
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4.71 out of 5 average rating, 121 reviews
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Luxe
Home in Anna Maria
Bridge and Bay Escape - Incredible Bay Views
4 bedrooms, 5 beds, 5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 12 reviews
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Top guest favourite
Home in Anna Maria
Prime Location! Waterfront! Walk to it all! Beach!
4 bedrooms, 6 beds, 4.5 bathrooms
24–29 Oct
5.0 out of 5 average rating, 18 reviews
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Top guest favourite
Home in Anna Maria
Magnolia Palms: Family Retreat w/ Backyard Oasis
3 bedrooms, 6 beds, 2 bathrooms
6–11 Dec
5.0 out of 5 average rating, 24 reviews
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Top guest favourite
Home in Holmes Beach
NEW! w/ Pool - The Pearl Unit 2 on AMI
2 bedrooms, 2 beds, 1.5 bathrooms
20–27 Sept
5.0 out of 5 average rating, 11 reviews
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Guest favourite
Home in Anna Maria
The Palm - BRAND NEW HOUSE!
5 bedrooms, 6 beds, 5.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Home in Anna Maria
Bean Pt. Bungalow - Half duplex w/private pool
3 bedrooms, 6 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 109 reviews
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Guest favourite
Home in Holmes Beach
Pineapple Paradise | Private Pool | Walk to Beach
2 bedrooms, 6 beds, 2 bathrooms
19–26 Sept
5.0 out of 5 average rating, 15 reviews
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Guest favourite
Home in Anna Maria
Anna Maria Beach House
4 bedrooms, 5 beds, 2.5 bathrooms
29 Sept – 5 Oct
4.98 out of 5 average rating, 41 reviews
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Superhost
Home in Anna Maria
Beachfront Bliss by Beach Boutique Rentals
5 bedrooms, 9 beds, 5.5 bathrooms
16–21 Oct
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Top guest favourite
Home in Anna Maria
Manatee Manor by Beach Boutique Rentals
3 bedrooms, 5 beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 31 reviews
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Guest favourite
Home in Holmes Beach
Island Getaway: Pool, Beach 1.5 Blocks, Dogs Yes!
2 bedrooms, 5 beds, 2 bathrooms
26 Sept – 3 Oct
5.0 out of 5 average rating, 10 reviews
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Superhost
Home in Anna Maria
North Shore Beach House: 4BR, Pool, Spa
4 bedrooms, 6 beds, 4 bathrooms
31 Oct – 5 Nov
4.75 out of 5 average rating, 4 reviews
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Guest favourite
Home in Holmes Beach
Black Pearl! NEW! Block and half to Beach!
4 bedrooms, 5 beds, 4 bathrooms
9–16 Nov
4.93 out of 5 average rating, 14 reviews
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Top guest favourite
Home in Holmes Beach
Beach cottage
2 bedrooms, 5 beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 13 reviews
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Guest favourite
Home in Holmes Beach
A Villa Paradise by Beach Boutique Rentals
3 bedrooms, 4 beds, 2 bathrooms
25 Oct – 1 Nov
4.98 out of 5 average rating, 42 reviews
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Top guest favourite
Home in Bradenton Beach
Gulf Front! Sunset Deck! + Walk to Bridge St Pier!
3 bedrooms, 5 beds, 1 bathroom
27 Sept – 2 Oct
4.98 out of 5 average rating, 128 reviews
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Top guest favourite
Home in Bradenton Beach
Walk to it all! Restaurants + Heated Pool +Beach!
3 bedrooms, 7 beds, 3 bathrooms
20–25 Sept
4.98 out of 5 average rating, 114 reviews
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Home in Holmes Beach
Lakefront · Fishing ·Heated Pool ·Walk to Beach
3 bedrooms, 3 beds, 3 bathrooms
19–26 Sept
New place to stay