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  • Captain's Quarters
    From $100 per night (USD)

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    Captain's Quarters

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Delightful private fully furnished one bedroom apartment on second floor of old Florida house located less than 100 feet ...

    From $100 per night (USD)

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  • How Lucky AMI
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    How Lucky AMI

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This beautiful, clean and conveniently located property on AMI is a new rental listing complete with fresh furnishings a ...

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  • 3011 Ave E-2
    From $143 per night (USD)

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    3011 Ave E-2

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    3011 Ave E-2 Triplex Condo 2 Bedroom/ 2 Bath ground floor , maximum occupancy of 6 people. VRC16-000051 Pet ...

    From $143 per night (USD)

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  • Club Bamboo South 125 Studio
    From $157 per night (USD)

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    Club Bamboo South 125 Studio

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    4

    Club Bamboo South unit 125, Gulf Front Studio, ocean view, maximum occupancy of 4 people, Max 1 vehicle. Community pool, ...

    From $157 per night (USD)

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  • *Ashore Thing* Beach Cottage
    From $259 per night (USD)

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    *Ashore Thing* Beach Cottage

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    9

    TO ALLOW FOR PROPER CLEANING AND DISNFECTION OF PROPERTY BETWEEN STAYS EARLY CHECK-INS AND LATE CHECK-OUTS WILL BE UNAVA ...

    From $259 per night (USD)

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  • Bradenton Beach Club A
    From $357 per night (USD)

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    Bradenton Beach Club A

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Bradenton Beach Club A - Condo 3 Bedroom/ 2 Bath ocean view, maximum occupancy of 6 people. 2 Community pools (1 g ...

    From $357 per night (USD)

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  • Island Paradise 2 at LayZLivin
    From $100 per night (USD)

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    Island Paradise 2 at LayZLivin

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    We are located 45 minutes south of St Petersburg, an hour south of the Tampa International airport, 2 hours from Orlando ...

    From $100 per night (USD)

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  • Island Beach Club 3
    From $171 per night (USD)

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    Island Beach Club 3

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Island Beach Club 3 - Condo 2 Bedroom / 1 Bath ground level gulf front , maximum occupancy of 4 people. Community ...

    From $171 per night (USD)

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  • Palm Oasis Duplex - West
    From $150 per night (USD)

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    Palm Oasis Duplex - West

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Palm Oasis Villa West is a 2 bedroom, 1 bath ground level condo that is walking distance to pristine Gulf beaches. This ...

    From $150 per night (USD)

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  • Beach Basket - 1300807
    From $150 per night (USD)

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    Beach Basket - 1300807

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    2/2+ Beach Cottage only steps to the white sandy beaches of Anna Maria Island! If you are looking for that Florida ...

    From $150 per night (USD)

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  • View of the Gulf
    From $365 per night (USD)

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    View of the Gulf

    Bedrooms:
    5.5
    Bathrooms:
    7
    Sleeps:
    14

    View of the Gulf is located in Holmes Beach, directly across from the white sandy beaches of Anna Maria! Enjoy views of ...

    From $365 per night (USD)

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  • Coquina Sands Unit B
    From $279 per night (USD)

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    Coquina Sands Unit B

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    6

    This gorgeous home is just steps to the beach, with other beautiful homes nearby. This beautiful home is one of two, wit ...

    From $279 per night (USD)

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  • Whispering Palms at NBV
    From $140 per night (USD)

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    Whispering Palms at NBV

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    7

    Whispering Palms Villa at North Beach Village is a bright and sunny, tastefully decorated beach style townhouse located ...

    From $140 per night (USD)

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  • MARLIN UNIT 204 CENTER UNIT
    From $240 per night (USD)

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    MARLIN UNIT 204 CENTER UNIT

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    THE Marlin is a triplex building. Unit 202 has one bedroom, one bath with a king bed and a queen sleeper sofa. Unit 20 ...

    From $240 per night (USD)

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  • A Island Breeze
    From $300 per night (USD)

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    A Island Breeze

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Located on Anna Maria Island off the Gulf Coast of Florida, Bradenton Beach is a small, friendly and charming old Florid ...

    From $300 per night (USD)

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  • Jacaranda
    From $179 per night (USD)

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    Jacaranda

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Unique 3 bedroom 2 baths with an upstairs bonus room. This gem was a loved family home for a few decades and has now be ...

    From $179 per night (USD)

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  • Bungalow On The Bayou
    From $320 per night (USD)

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    Bungalow On The Bayou

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Located on the "best" street on Anna Maria Island, this two-bedroom, one-bath second floor vacation rental with a specta ...

    From $320 per night (USD)

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  • Beach Front 1, 2318 Gulf Dr. N
    From $259 per night (USD)

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    Beach Front 1, 2318 Gulf Dr. N

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    1 Bedroom, 1 Bathroom, first story Condo/Studio directly on the beach, freshly painted with New Ductless Mini-Split AC/ ...

    From $259 per night (USD)

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  • Sandy Shores Condo
    From $150 per night (USD)

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    Sandy Shores Condo

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Don't miss out on this newly renovated 2 bedroom 2 bathroom 2nd floor condo with elevator on the West side of Gulf drive ...

    From $150 per night (USD)

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  • Pelican Perch (Upstairs)
    From $80 per night (USD)

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    Pelican Perch (Upstairs)

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Video Tour link at the bottom. This cottage is located "on the beach" 3007 Avenue F on beautiful Holmes beach. It is th ...

    From $80 per night (USD)

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  • Ocean Walk
    From $275 per night (USD)

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    Ocean Walk

    Bedrooms:
    4.5
    Bathrooms:
    4
    Sleeps:
    12

    Ocean Walk is located West of Gulf Drive so there are no busy roads to cross and only a 1 minute stroll to the Gulf beac ...

    From $275 per night (USD)

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  • 214 Sycamore
    From $250 per night (USD)

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    214 Sycamore

    Bedrooms:
    5.5
    Bathrooms:
    4
    Sleeps:
    8

    Just 5 houses from the white sandy beach of the Gulf. Near the heart of Anna Maria village sits this spacious home wit ...

    From $250 per night (USD)

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  • Runaway Bay 261
    From $114 per night (USD)

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    Runaway Bay 261

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Runaway Bay 261 - Across the street from the beach - Condo 2 Bedroom/ 2 Bath , maximum occupancy of 4 people. Comm ...

    From $114 per night (USD)

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  • Siesta Sol Cottage
    From $125 per night (USD)

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    Siesta Sol Cottage

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Lovely, conveniently located ground level home in the heart of Holmes Beach. This two bedroom home has it all. Newly ins ...

    From $125 per night (USD)

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  • Seaside Maison
    From $275 per night (USD)

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    Seaside Maison

    Bedrooms:
    5.5
    Bathrooms:
    4
    Sleeps:
    8

    You won't be disappointed with this brand new home! This home has 4 bedrooms each with an en-suite washroom, home is loc ...

    From $275 per night (USD)

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  • Martinique 505 South
    From $129 per night (USD)

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    Martinique 505 South

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Must be booked 30 days in advance. VRC#20-000110 Martinique 505 South - Condo 2 Bedroom / 2 Bath gulf view ...

    From $129 per night (USD)

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  • Mango Breeze
    From $172 per night (USD)

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    Mango Breeze

    Bedrooms:
    4.5
    Bathrooms:
    4
    Sleeps:
    8

    Mango Breeze is tucked away in the heart of Holmes Beach, located just 6 homes away from the Gulf beaches! Come getaway ...

    From $172 per night (USD)

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  • Sea Pirate Cottage By The Sea
    From $105 per night (USD)

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    Sea Pirate Cottage By The Sea

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Cottage By the Sea is a (no smoking) Unit within the charming Sea Pirate condo complex located on a tranquil and desir ...

    From $105 per night (USD)

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  • Island Sol
    From $300 per night (USD)

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    Island Sol

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    14

    Island Sol is a custom luxury home in Bradenton Beach that features stunning views of the Bay and just 2 blocks away fro ...

    From $300 per night (USD)

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  • Bradenton Beach Club 228
    From $186 per night (USD)

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    Bradenton Beach Club 228

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Bradenton Beach Club 228 - Condo 2 Bedroom/ 2 Bath, maximum occupancy of 6 people. Distance to the Beach: across ...

    From $186 per night (USD)

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  • Beach Front 4, 2318Gulf Dr. N.
    From $309 per night (USD)

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    Beach Front 4, 2318Gulf Dr. N.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Two Bedroom, Two Bathroom, second story Condo directly on the beach. Large deck to enjoy best sunsets on Anna Maria. B ...

    From $309 per night (USD)

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  • MI Oasis Getaway
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    MI Oasis Getaway

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    COVID-19 update: we believe in being fair to all of our guests, if you are unable to travel due to restrictions from yo ...

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  • Casa By The Beach
    From $425 per night (USD)

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    Casa By The Beach

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    12

    Casa by the Beach is a newly renovated duplex with 3 bedrooms and 2 full baths upstairs and 3 bedrooms and 2 full baths ...

    From $425 per night (USD)

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  • Sunset Cottage
    From $200 per night (USD)

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    Sunset Cottage

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to Sunset Cottage, the perfect place to experience island life. Just outside your back door is the famous Captai ...

    From $200 per night (USD)

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  • Beachside Oasis
    From $404 per night (USD)

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    Beachside Oasis

    Bedrooms:
    4.5
    Bathrooms:
    5
    Sleeps:
    14

    Please take note that this rental is mostly Saturday to Saturday only unless you message the owner first. Come and fall ...

    From $404 per night (USD)

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  • White Sands
    From $150 per night (USD)

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    White Sands

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    White Sands is in the perfect location! This charming beach cottage is located right on the beautiful Gulf of Mexico in ...

    From $150 per night (USD)

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  • Beach Please
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    Beach Please

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Beach Please! A beautifully maintained Anna Maria Island home, conveniently located in central Holmes Beach. ...

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  • Siblings & Sunshine
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    Siblings & Sunshine

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    "Siblings & Sunshine" is the east side of this adorable duplex in Bradenton Beach. It features 2 bedrooms, 2 full bathro ...

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  • SUNNYSIDE-AMI
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    SUNNYSIDE-AMI

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    We have developed a comprehensive Safety / Cleaning / Sanitation Plan and work with an amazing team to ensure the home & ...

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  • Caribbean Dream
    From $350 per night (USD)

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    Caribbean Dream

    Bedrooms:
    5.5
    Bathrooms:
    5
    Sleeps:
    10

    Caribbean Dream is a stunning, luxury home in Holmes Beach located just a short 3-minute walk to the Gulf beaches! This ...

    From $350 per night (USD)

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  • Pelican Perch (Downstairs)
    From $180 per night (USD)

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    Pelican Perch (Downstairs)

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Video Tour Link at the bottom This cottage is located "on the beach" 3007 Avenue F, beautiful Holmes beach. It is th ...

    From $180 per night (USD)

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  • Antigua Bay
    From $325 per night (USD)

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    Antigua Bay

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    Antigua Bay is a stunning island home located on the prestigious North end of Anna Maria Island, closely located to loca ...

    From $325 per night (USD)

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  • Sunsets on Carissa
    From $319 per night (USD)

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    Sunsets on Carissa

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to Sunsets on Carissa! On Anna Maria Island (Holmes Beach, FL) Managed by Once Upon A Beach Vacation Rentals, a ...

    From $319 per night (USD)

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  • Gulf Beach Apartment - with Pool & Beach Access
    From $125 per night (USD)

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    Gulf Beach Apartment - with Pool & Beach Access

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Pristine,spacious1 bedroom apartment sleeps 4, only steps to the beautiful white sandy beach of Anna Marie Island. Fresh ...

    From $125 per night (USD)

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  • Bradenton Beach Club Unit C
    From $250 per night (USD)

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    Bradenton Beach Club Unit C

    Bedrooms:
    3.5
    Bathrooms:
    3
    Sleeps:
    6

    Bradenton Beach Club Unit C is a direct Gulf front Mediterranean style condo, with the best sunset views from the privac ...

    From $250 per night (USD)

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  • She's Always Right
    From $639 per night (USD)

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    She's Always Right

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to She's Always Right! On Anna Maria Island (Holmes Beach, FL) Managed by Once Upon A Beach Vacation Rentals, a ...

    From $639 per night (USD)

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  • Casita Marina 11101 Gulf Dr. N
    From $359 per night (USD)

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    Casita Marina 11101 Gulf Dr. N

    Bedrooms:
    3.5
    Bathrooms:
    3
    Sleeps:
    8

    This classic home located on the North End of Anna Maria Island is the perfect home for your tropical beach vacation. Th ...

    From $359 per night (USD)

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  • Castnetter Beach Resort 6
    From $59 per night (USD)

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    Castnetter Beach Resort 6

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Our Holmes Beach property is located at Gulf Drive & 41st Street. Conveniently located at the (7) Acre Lifeguard protec ...

    From $59 per night (USD)

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  • 313 Island Walk
    From $157 per night (USD)

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    313 Island Walk

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Island Walk 313 - Townhouse 3 Bedroom/ 2 .5 Bath with private pool , maximum occupancy of 6 people. VRC16-000052 ...

    From $157 per night (USD)

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  • Calypso Cottage
    From $150 per night (USD)

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    Calypso Cottage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Calypso Cottage is a Mediterranean style home on Anna Maria Island, just a 5 minute stroll to the Gulf beaches! This ho ...

    From $150 per night (USD)

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  • Shell Game - 1683476
    From $170 per night (USD)

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    Shell Game - 1683476

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Playa Encantada Beacfront Community just Steps to the Beach Shell Game has recently been transformed into a fun an ...

    From $170 per night (USD)

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  • HLC #2 Tranquility - Harbor La
    From $154 per night (USD)

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    HLC #2 Tranquility - Harbor La

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Just 300 steps from the beach, Harbor Lane Court is a 4 unit resort, with 3 one bedroom, one bath apartments, and one tw ...

    From $154 per night (USD)

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  • Island Breeze Unit B
    From $300 per night (USD)

    VRBO

    Island Breeze Unit B

    Bedrooms:
    3.5
    Bathrooms:
    3
    Sleeps:
    6

    Located on Anna Maria Island off the Gulf Coast of Florida, Bradenton Beach is a small, friendly and charming old Florid ...

    From $300 per night (USD)

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  • Sunset Penthouse
    From $350 per night (USD)

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    Sunset Penthouse

    Bedrooms:
    3.5
    Bathrooms:
    4
    Sleeps:
    8

    Sunset Penthouse is a direct Gulf front condo with private elevator and private garage, and the best sunset views from t ...

    From $350 per night (USD)

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  • Bay Breeze #3
    From $335 per night (USD)

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    Bay Breeze #3

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    7

    Summary: Bay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the ...

    From $335 per night (USD)

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    Details
  • Garden Apartment 4
    From $85 per night (USD)

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    Garden Apartment 4

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Our five unit property was featured in the January/February 2020 issue of Southern Living, and we are honored and thrill ...

    From $85 per night (USD)

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  •  The Ballyhoo
    From $59 per night (USD)

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    The Ballyhoo

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    The Ballyhoo is a ground floor rental on historic Bean Point in Anna Maria City. 200 feet to the beach, the Rod & Reel P ...

    From $59 per night (USD)

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  • GREAT VENTURE GETAWAY
    From $145 per night (USD)

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    GREAT VENTURE GETAWAY

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This TOP FLOOR DUPLEX is centrally located on Anna Maria Island and is convenient to the island's free trolley which wi ...

    From $145 per night (USD)

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  • Gulfside Oasis
    From $350 per night (USD)

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    Gulfside Oasis

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    12

    With numerous views of the Gulf- Gulfside Oasis is only a minute walk away from the sandy beaches and the famous Beach B ...

    From $350 per night (USD)

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  • Shady Palms
    From $175 per night (USD)

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    Shady Palms

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    6

    Shady Palms is a clean and cozy beach cottage right on the beautiful Gulf of Mexico. Walk out the back door to a large s ...

    From $175 per night (USD)

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  • The Blue Horizon
    From $700 per night (USD)

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    The Blue Horizon

    Bedrooms:
    8.5
    Bathrooms:
    9
    Sleeps:
    21

    The Blue Horizon is the perfect luxury, beach-front home that can sleep the whole family! Wedding parties are allowed (w ...

    From $700 per night (USD)

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  • Bradenton Beach Club 238
    From $143 per night (USD)

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    Bradenton Beach Club 238

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Bradenton Beach Club 238 - Condo 2 Bedroom/ 2 Bath, maximum occupancy of 6 people. Distance to the Beach: across t ...

    From $143 per night (USD)

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  • Garden Apartment 2
    From $85 per night (USD)

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    Garden Apartment 2

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Stay with us if you like: * A place right on the beach with no busy streets to cross. * Your own private sun patio with ...

    From $85 per night (USD)

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    Details
  • Bradenton Beach Club 247
    From $171 per night (USD)

    VRBO

    Bradenton Beach Club 247

    Bedrooms:
    3.5
    Bathrooms:
    3
    Sleeps:
    6

    Bradenton Beach Club 247 - Condo 3 Bedroom/ 2 1/2 Bath, maximum occupancy of 6 people. Distance to the Beach: acr ...

    From $171 per night (USD)

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  • Blue Sky Beach House
    From $300 per night (USD)

    VRBO

    Blue Sky Beach House

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    Relax in this comfy, coastal home just a block from the beautiful beaches of Anna Maria Island. The Blue Sky Beach Hous ...

    From $300 per night (USD)

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  • Beach Life At The Pointe
    From $150 per night (USD)

    VRBO

    Beach Life At The Pointe

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Beach Life at the Point is your ideal slice of Old Florida on the beautiful beaches of Anna Maria Island. Enjoy amazing ...

    From $150 per night (USD)

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  • Comfortable family-friendly condo close to everything on Anna Maria.
    From $184 per night (USD)

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    Comfortable family-friendly condo close to everything on Anna Maria.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This stylish coastal getaway at Sandy Pointe is a spacious 2-bedroom condo, centrally located on Anna Maria close to sho ...

    From $184 per night (USD)

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    Details
  • Club Bamboo South 123 Studio
    From $157 per night (USD)

    VRBO

    Club Bamboo South 123 Studio

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    4

    Club Bamboo South unit 123, Gulf Front Studio, ocean view, maximum occupancy of 4 people, Max 1 vehicle. Community pool, ...

    From $157 per night (USD)

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  • Beachfront Paradise
    From $650 per night (USD)

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    Beachfront Paradise

    Bedrooms:
    5.5
    Bathrooms:
    6
    Sleeps:
    18

    Looking for a place to get away from the world? Our house provides everything you could possibly dream of in an Anna Ma ...

    From $650 per night (USD)

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  • Costa Lotta on Anna Maria
    From $259 per night (USD)

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    Costa Lotta on Anna Maria

    Bedrooms:
    4.5
    Bathrooms:
    3
    Sleeps:
    6

    Fantastic Location. 200 feet to the beach - a short one minute stroll - Gulf Views. Three story spacious luxury home. ...

    From $259 per night (USD)

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  • MARLIN UNIT 202 WEST UNIT
    From $240 per night (USD)

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    MARLIN UNIT 202 WEST UNIT

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    THE Marlin is a triplex building. Unit 202 has one bedroom, one bath with a king bed and a queen sleeper sofa. Unit 2 ...

    From $240 per night (USD)

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  • Mermaids Crossing
    From $150 per night (USD)

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    Mermaids Crossing

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Mermaids Crossing is a newly renovated ground level home, located just 2 minutes away from the white sandy beaches of th ...

    From $150 per night (USD)

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  • CBC
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    CBC

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    2

    Studio unit, sleeps 2, has everything you need.. No street crossing for the Gulf!! Quiet complex with covered parking s ...

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  • Beach Side Vista
    From $250 per night (USD)

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    Beach Side Vista

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    14

    Beach Side Vista is an elevated private home that is just steps away from the Gulf of Mexico in Bradenton Beach! This h ...

    From $250 per night (USD)

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  • Vitamin Sea
    From $383 per night (USD)

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    Vitamin Sea

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    12

    BOOK WITH CONFIDENCE ALL RESERVATIONS MADE AFTER FEBRUARY 18TH 2021, WILL BE REFUNDED 85% OF THE TOTAL BOOKING COST IF C ...

    From $383 per night (USD)

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  • Casa Mariposa
    From $99 per night (USD)

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    Casa Mariposa

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to Casa Mariposa! On Anna Maria Island (Anna Maria, FL) Managed by Once Upon A Beach Vacation Rentals, a locally ...

    From $99 per night (USD)

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  • Villa Rayo De Sol
    From $500 per night (USD)

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    Villa Rayo De Sol

    Bedrooms:
    6.5
    Bathrooms:
    5
    Sleeps:
    16

    Villa Rayo De Sol is a direct gulf front home that has been recently completely renovated! This larger than life compoun ...

    From $500 per night (USD)

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  • Turtle Watch
    From $225 per night (USD)

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    Turtle Watch

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Turtle Watch is a direct Gulf front, elevated home located in Holmes Beach! Enjoy Sunset views from the privacy of your ...

    From $225 per night (USD)

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  • Crosswind Cottage
    From $149 per night (USD)

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    Crosswind Cottage

    Bedrooms:
    3.5
    Bathrooms:
    3
    Sleeps:
    6

    BOOK WITH CONFIDENCE ALL RESERVATIONS MADE AFTER FEBRUARY 18TH 2021, WILL BE REFUNDED 85% OF THE TOTAL BOOKING COST IF C ...

    From $149 per night (USD)

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  • The Big Yellow House
    From $350 per night (USD)

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    The Big Yellow House

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    14

    The Big Yellow House on Pine Avenue is a direct Gulf front home with a private heated pool and right across the street f ...

    From $350 per night (USD)

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  • Palm Isle Retreat PIR
    From $209 per night (USD)

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    Palm Isle Retreat PIR

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    95 five-star reviews says it all! Florida's best kept secret, Anna Maria Island, features beautiful white sugar sand be ...

    From $209 per night (USD)

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  • Spoonbill Hideaway
    From $245 per night (USD)

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    Spoonbill Hideaway

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Our house is located on North Shore Drive in Anna Maria Florida across the street from one of the widest and finest beac ...

    From $245 per night (USD)

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  • Moon Shadow South - 1381834
    From $243 per night (USD)

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    Moon Shadow South - 1381834

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Spectacular Location on the North End of Anna Maria with Heated Pool! Moon Shadow South's location can't be beat w ...

    From $243 per night (USD)

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  • 266 S Harbor
    From $118 per night (USD)

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    266 S Harbor

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    266 S. Harbor - Private home 3 Bedroom/ 2 Bath , maximum occupancy of 6 people. Distance to the Beach: 3 blocks ...

    From $118 per night (USD)

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  • AMI Beach Home - BEAUTIFUL POOL HOME! STEPS TO THE BEACH!
    From $225 per night (USD)

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    AMI Beach Home - BEAUTIFUL POOL HOME! STEPS TO THE BEACH!

    Bedrooms:
    5.5
    Bathrooms:
    4
    Sleeps:
    10

    Welcome to the AMI Beach Home on beautiful Anna Maria Island Visit AMI Beach Home, a marvelous custom-built ground flo ...

    From $225 per night (USD)

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  • Runaway Bay 205
    From $102 per night (USD)

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    Runaway Bay 205

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Runaway Bay 205 - Across the street from the beach- Condo 2 Bedroom/ 2 Bath , maximum occupancy of 4 people. Commu ...

    From $102 per night (USD)

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  • Club Bamboo South 225 Studio
    From $157 per night (USD)

    VRBO

    Club Bamboo South 225 Studio

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    4

    Club Bamboo South unit 225, Gulf Front Studio, ocean view, maximum occupancy of 4 people, Max 1 vehicle. Community pool, ...

    From $157 per night (USD)

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  • Tortuga Tides
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    Tortuga Tides

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Tortuga tides is your extended vacation oasis steps from the white sands of Anna Maria Island beaches. The master bedroo ...

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  • 3011 Ave E-3
    From $136 per night (USD)

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    3011 Ave E-3

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    3011 Ave E-3 - Triplex Condo 1 Bedroom/ 1 Bath , maximum occupancy of 4 people. VRC16-000051 Pet friendly. ...

    From $136 per night (USD)

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  • Emerald Bay
    From $230 per night (USD)

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    Emerald Bay

    Bedrooms:
    4.5
    Bathrooms:
    3
    Sleeps:
    6

    BOOK WITH CONFIDENCE ALL RESERVATIONS MADE AFTER FEBRUARY 18TH 2021, WILL BE REFUNDED 85% OF THE TOTAL BOOKING COST IF C ...

    From $230 per night (USD)

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  • Coquina Beach Club 102
    From $221 per night (USD)

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    Coquina Beach Club 102

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Coquina Beach Club 102 - Condo 2 Bedroom/ 2 Bath ocean view, maximum occupancy of 6 people. Community pool. ...

    From $221 per night (USD)

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  • Ocean Front ~ No Streets To Cross!  Come And Enjoy A Memorable Beach Vacation!
    From $130 per night (USD)

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    Ocean Front ~ No Streets To Cross! Come And Enjoy A Memorable Beach Vacation!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This complex at 7100 Gulf Drive is well managed, impeccably maintained and has a reputation of being one of the island's ...

    From $130 per night (USD)

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  • Sandy Point 111
    From $114 per night (USD)

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    Sandy Point 111

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Sandy Point 111 - Condo 2 Bedroom/ 2 Bath, maximum occupancy of 4 people. Distance to the Beach: 4 blocks VR ...

    From $114 per night (USD)

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  •  Coquina Beach Club
    From $159 per night (USD)

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    Coquina Beach Club

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    2

    EXTRA CLEAN UNIT!! This studio sleeps 2. Fully furnished, QUEEN BISCAYNE MATTRESS (BED) & QUEEN SLEEPER SOFA BED. Washe ...

    From $159 per night (USD)

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  • Blue Heron Cottage
    From $120 per night (USD)

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    Blue Heron Cottage

    Bedrooms:
    3.5
    Bathrooms:
    1
    Sleeps:
    4

    Great 1 bedroom, 1.5 bathroom cottage on the quiet north end of island. The house is conveniently located and within wal ...

    From $120 per night (USD)

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  • Surf Rider's Cottage
    From $114 per night (USD)

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    Surf Rider's Cottage

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    99

    Welcome to Surf Rider's Cottage! NOW with PRIVATE POOL! West of Gulf Drive, this cute Island bungalow is just perf ...

    From $114 per night (USD)

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  • Club Bamboo South 119 Studio
    From $157 per night (USD)

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    Club Bamboo South 119 Studio

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    3

    Club Bamboo South unit 119, Gulf Front Studio, ocean view, maximum occupancy of 4 people, Max 1 vehicle. Community pool, ...

    From $157 per night (USD)

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  • SUGAR REEF - Unit A
    From $159 per night (USD)

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    SUGAR REEF - Unit A

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Anna Maria Island Retreat! The tranquility and luxury you desire is at Sugar Reef. All new, inside and out! Sugar Ree ...

    From $159 per night (USD)

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  • LAZY PALM COTTAGE
    From $225 per night (USD)

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    LAZY PALM COTTAGE

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    CLEANLINESS HAS ALWAYS BEEN A TOP PRIORITY. WE WANT YOU TO KNOW THAT WE ARE DOING OUR PART TO HELP OUR GUESTS STAY SAFE ...

    From $225 per night (USD)

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  • OHasis Getaway
    From $125 per night (USD)

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    OHasis Getaway

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    COVID-19 update: we believe in being fair to all of our guests, if you are unable to travel due to restrictions from yo ...

    From $125 per night (USD)

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