Over 1,000 stays

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Superhost
Home in Holmes Beach
The Peachy Beach House, steps to the gulf
4 beds
Sep. 19 – 26
$391 CAD per night
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Home in Holmes Beach
Sandy Toes: 1 Block to the Beach, Dog Friendly by Anna Maria Life Vacation Rentals
2 king beds
Oct. 24 – 31
$308 CAD per night
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Apartment in Holmes Beach
Crows Nest at Spinnakers Vacation Cottages
4 beds
Oct. 22 – 29
$321 CAD per night, originally $413
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Apartment in Holmes Beach
Spectacular home 700 feet from the beach!
4 beds
Oct. 22 – 29
$429 CAD per night, originally $468
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Superhost
Home in Holmes Beach
Unwind SUNSHINE..tropical oasis, heated pool
7 beds
Dec. 9 – 16
$865 CAD per night
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Superhost
Cottage in Holmes Beach
NEW LISTING! Sailfish Gulf Suites #3, Modern Ameni
2 beds
May 9 – 16
$447 CAD per night
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Superhost
Cottage in Holmes Beach
🏝Calypso-an Anna Maria Island Private Oasis!🏖
3 beds
Nov. 26 – Dec. 3
$538 CAD per night
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Cottage in Anna Maria
Turtle Cottage - Anna Maria Island
2 beds
Jul. 25 – Aug. 1
$521 CAD per night
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Superhost
Home in Anna Maria
Anna Cabana B
1 sofa bed
Nov. 4 – 11
$372 CAD per night
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Bungalow in Holmes Beach
"A" Gulf Beach Bungalow
2 double beds
Jul. 10 – 17
$189 CAD per night
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Superhost
Home in Anna Maria
3br/2b in Anna Maria w/ Private Heated Pool Oasis
4 beds
Nov. 5 – 12
$551 CAD per night, originally $623
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Condo in Holmes Beach
Beachfront Bungalow! Newly updated 1 bedroom!
2 queen beds
Oct. 1 – 8
$515 CAD per night
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Apartment in Holmes Beach
Little Dream by Anna Maria Island Accommodations
2 beds
Sep. 10 – 17
$202 CAD per night
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Superhost
Condo in Holmes Beach
Anna Maria Island-just a few steps to the beach
3 beds
Oct. 20 – 27
$352 CAD per night
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Superhost
Home in Holmes Beach
AMI Sand Dollar
2 beds
Apr. 29 – May 6
$443 CAD per night
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Condo in Holmes Beach
Anna Maria Beach Place...footsteps to the sands
1 bed
Jul. 23 – 30
$328 CAD per night, originally $353
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Superhost
Home in Holmes Beach
Key Lime Cottage by Beach Boutique Rentals
4 beds
Nov. 4 – 11
$474 CAD per night
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Superhost
Condo in Holmes Beach
Spacious Condo On the Beach
4 beds
Dec. 3 – 10
$449 CAD per night
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Superhost
Home in Holmes Beach
Fall discount! The Palms AMI- 2BR/2BA vrc 000075
4 beds
Jun. 4 – 11
$244 CAD per night
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Condo in Anna Maria
Budget-Friendly Condo in Great Location w/Shared Pool, Washer/Dryer, & Free WiFi
2 beds
Sep. 12 – 19
$266 CAD per night, originally $387