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Holmes Beach Rentals

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  • Beach House II
    From $385 per night (USD)

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    Beach House II

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    We highly recommend TRIP INSURANCE Steps to the BEACH family vacation, near shops, restaurants, banks, trolly, beach wi ...

    From $385 per night (USD)

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    Details
  • Beach Bungalow - B
    From $90 per night (USD)

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    Beach Bungalow - B

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Vacation to the perfect quiet spot on Anna Maria Island! The newly remodeled two bathroom, one bathroom condo is only st ...

    From $90 per night (USD)

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  • Lemon Cottage 6808.Holmes
    From $119 per night (USD)

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    Lemon Cottage 6808.Holmes

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Lemon Cottage located just 2 blocks from the Gulf beaches of Anna Maria Island. Lemon Cottage is a ground lev ...

    From $119 per night (USD)

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  • Castnetter Beach Resort 5
    From $110 per night (USD)

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    Castnetter Beach Resort 5

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Anna Maria Island's "Castnetter 5" is a delightful Island local located directly across the street from the seven acre " ...

    From $110 per night (USD)

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  • Holmes Sweet Home
    From $150 per night (USD)

    VRBO

    Holmes Sweet Home

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Upper Duplex Home located steps from the Gulf of Mexico, this Beach Bungalow with Pool is perfect for couples and famili ...

    From $150 per night (USD)

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    Details
  • LimeKiss Unit B
    From $168 per night (USD)

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    LimeKiss Unit B

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to LimeKiss, Unit B! This stunningly decorated 3 bedroom, 2 bathroom duplex rental home located steps to the bea ...

    From $168 per night (USD)

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  • Gulf Sands, on the beach!
    From $269 per night (USD)

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    Gulf Sands, on the beach!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Just remodeled in October 2019. Beautiful turquoise Gulf of Mexico waters, 7 miles of white sand beach, your own private ...

    From $269 per night (USD)

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    Details
  • Runaway Bay 249
    From $129 per night (USD)

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    Runaway Bay 249

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Tucked away on a peaceful canal and steps to beautiful beaches, this tastefully decorated condo is the perfect location ...

    From $129 per night (USD)

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  • The Beach Club At Anna Maria #2
    From $100 per night (USD)

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    The Beach Club At Anna Maria #2

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    RVA features The Beach Club at Anna Maria. Old Florida charm meets modern, designer-decorated decor at this private, un- ...

    From $100 per night (USD)

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  • LAY-Z LIVN - 7
    From $86 per night (USD)

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    LAY-Z LIVN - 7

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    This clean and comfortable 2 bedroom, 1 bath, ground floor unit is located just a block and a half from the beautiful Gu ...

    From $86 per night (USD)

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    Details
  • HOLMES BEACH RETREAT
    From $114 per night (USD)

    VRBO

    HOLMES BEACH RETREAT

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Just a stone's throw from the Gulf, this clean and comfortable 2 bedroom / 2 bathroom cottage is the perfect place to ge ...

    From $114 per night (USD)

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    Details
  • Sirenia Beach House
    From $255 per night (USD)

    VRBO

    Sirenia Beach House

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    $1,999/wk plus fees and taxes - available December dates have been heavily discounted. Book your vacay today! Just ren ...

    From $255 per night (USD)

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    Details
  • The Beach Club At Anna Maria #7
    From $85 per night (USD)

    VRBO

    The Beach Club At Anna Maria #7

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    2

    RVA features The Beach Club at Anna Maria. Old Florida charm meets modern, designer-decorated decor at this private, un- ...

    From $85 per night (USD)

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    Details
  • Unit 12 - Townhouse 3 Bedroom
    From $339 per night (USD)

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    Unit 12 - Townhouse 3 Bedroom

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    The interior decor in your private Holmes Beach vacation rental is elegant, fresh and bright. These three bedroom, three ...

    From $339 per night (USD)

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    Details
  • Unit 6 - Second Floor Standard 2 Bedroom
    From $309 per night (USD)

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    Unit 6 - Second Floor Standard 2 Bedroom

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    6

    The stunning interiors in your private Holmes Beach vacation rental are elegant, fresh and bright. The two bedroom, 2.5 ...

    From $309 per night (USD)

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    Details
  • The beach house
    From $209 per night (USD)

    VRBO

    The beach house

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    We highly recommend TRIP INSURANCE Home away from home, cozy and comfortable Beach house. A 5 minute walk to the beach ...

    From $209 per night (USD)

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  • AMI Canal House on Gladstone
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    AMI Canal House on Gladstone

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Canal House Canal House is a renovated and designer- decorated three bedroom vacation home in the highly coveted Key R ...

    Click For Pricing

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  • Sirenia Cove
    From $255 per night (USD)

    VRBO

    Sirenia Cove

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    November and Early December rates have been heavily discounted. Book a fab vacay now! We have work and home study spac ...

    From $255 per night (USD)

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    Details
  • The Beach Club At Anna Maria #1
    From $85 per night (USD)

    VRBO

    The Beach Club At Anna Maria #1

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    RVA features The Beach Club at Anna Maria. Old Florida charm meets modern, designer-decorated decor at this private, un- ...

    From $85 per night (USD)

    VRBO

    Details
  • Anna Maria Island Beach Paradise 6
    From $150 per night (USD)

    VRBO

    Anna Maria Island Beach Paradise 6

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    An addendum to our cancellation policy: If the governor of Florida issues a Florida travel ban you will receive a refund ...

    From $150 per night (USD)

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    Details
  • Anna Maria Island Beach Paradise 10
    From $125 per night (USD)

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    Anna Maria Island Beach Paradise 10

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    An addendum to our cancellation policy: If the governor of Florida issues a Florida travel ban you will receive a refund ...

    From $125 per night (USD)

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    Details
  • 2203 Avenue C, Bradenton Beach
    From $655 per night (USD)

    VRBO

    2203 Avenue C, Bradenton Beach

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    WHAT PRIOR GUESTS HAVE SAID ABOUT HOW WE HAVE HANDLED COVID-19 RELATED RESERVATIONS: Jen and Joe were gracious and gene ...

    From $655 per night (USD)

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    Details
  • Anna Maria Island Absolute Anna Maria-Private Beach Access-Heated Pool-Wi-Fi
    From $150 per night (USD)

    VRBO

    Anna Maria Island Absolute Anna Maria-Private Beach Access-Heated Pool-Wi-Fi

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Cancellations: An addendum to our cancellation policy: If the governor of Florida issues a Florida travel ban you will r ...

    From $150 per night (USD)

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    Details
  • Resort Sixty-Six
    From $110 per night (USD)

    VRBO

    Resort Sixty-Six

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Resort Sixty Six is a small 2 story resort located within steps of the ocean. 2nd floor studio room features newly remo ...

    From $110 per night (USD)

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    Details
  • 506 74th St
    From $209 per night (USD)

    VRBO

    506 74th St

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    This beautiful ground level waterfront home gives you the best that island living has to offer. Situated in tranquil Ho ...

    From $209 per night (USD)

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    Details
  • The Toasty Coconut
    From $550 per night (USD)

    VRBO

    The Toasty Coconut

    Bedrooms:
    3.5
    Bathrooms:
    4
    Sleeps:
    8

    Relaxing 'Home Away from Home' Tropical Paradise - 3 Houses from the beach. Located on the quiet, North end of the Islan ...

    From $550 per night (USD)

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    Details
  • Unit 7 - Third Floor Beach Front 3 Bedroom
    From $409 per night (USD)

    VRBO

    Unit 7 - Third Floor Beach Front 3 Bedroom

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Our spacious three bedroom beachfront retreats offer up to 1,627 square feet of fully furnished living space, perfect fo ...

    From $409 per night (USD)

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    Details
  • Unit 3 - First Floor Standard 2 Bedroom
    From $309 per night (USD)

    VRBO

    Unit 3 - First Floor Standard 2 Bedroom

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    6

    The stunning interiors in your private Holmes Beach vacation rental are elegant, fresh and bright. The two bedroom, 2 ba ...

    From $309 per night (USD)

    VRBO

    Details
  • Anna Maria Beach Place, Unit 1
    From $156 per night (USD)

    VRBO

    Anna Maria Beach Place, Unit 1

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    VRC16-000522 Anna Maria Beach Place 1 is thoroughly cleaned and sanitized prior to your arrival. We pay special attent ...

    From $156 per night (USD)

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    Details
  • Ocean View Suites
    From $95 per night (USD)

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    Ocean View Suites

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Come and stay at this beach side vacation rental on Anna Maria Island. This unit is located on the ground floor of a qua ...

    From $95 per night (USD)

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    Details
  • Cottage short stroll to beach
    From $250 per night (USD)

    VRBO

    Cottage short stroll to beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Anna Maria Island ''paradise without an attitude''. Our ground level newly renovated unit is located in t ...

    From $250 per night (USD)

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    Details
  • Island House - Funboard
    From $75 per night (USD)

    VRBO

    Island House - Funboard

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Location, location, location, this cozy quaint beach house is centrally located on Anna Maria Island and is less than a ...

    From $75 per night (USD)

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    Details
  • Anna Maria Island Retreat
    From $150 per night (USD)

    VRBO

    Anna Maria Island Retreat

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    An addendum to our cancellation policy: If the governor of Florida issues a Florida travel ban you will receive a refund ...

    From $150 per night (USD)

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    Details
  • Anna Maria Island Beach Home
    From $345 per night (USD)

    VRBO

    Anna Maria Island Beach Home

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Bright, sunny, spacious and clean townhouse in a great location on Anna Maria Island, just a few minutes walk to the oce ...

    From $345 per night (USD)

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    Details
  • Loggerhead Beach House 7508.Gulf
    From $119 per night (USD)

    VRBO

    Loggerhead Beach House 7508.Gulf

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    5

    Welcome to Loggerhead Beach House just a few houses from the Gulf beaches on Anna Maria Island. Loggerhead Beach House i ...

    From $119 per night (USD)

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    Details
  • Beach Dance
    From $379 per night (USD)

    VRBO

    Beach Dance

    Bedrooms:
    6.5
    Bathrooms:
    5
    Sleeps:
    10

    Beach Dance is the perfect family home in a convenient location just steps to the Gulf, Restaurants, Shops and the Free ...

    From $379 per night (USD)

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    Details
  • Anna Maria Island Beach Palms 2A
    From $115 per night (USD)

    VRBO

    Anna Maria Island Beach Palms 2A

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    An addendum to our cancellation policy: If the governor of Florida issues a Florida travel ban you will receive a refund ...

    From $115 per night (USD)

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    Details
  • Yellowfin Cottage 110.75th
    From $136 per night (USD)

    VRBO

    Yellowfin Cottage 110.75th

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Yellowfin Cottage located just 2 houses from the Gulf beaches on Anna Maria Island. Yellowfin Cottage is a gr ...

    From $136 per night (USD)

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    Details
  • LAY-Z LIV-N - 3
    From $86 per night (USD)

    VRBO

    LAY-Z LIV-N - 3

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This lovely ground floor unit is located just one block east of the inviting sands of the Gulf beaches of Anna Maria Isl ...

    From $86 per night (USD)

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    Details
  • Island House - Shortboard
    From $50 per night (USD)

    VRBO

    Island House - Shortboard

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Come and enjoy the beach life at this three bedroom beach cottage just 150 meters from the sandy shores of Holmes Beach. ...

    From $50 per night (USD)

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  • The Beach Club At Anna Maria #14
    From $100 per night (USD)

    VRBO

    The Beach Club At Anna Maria #14

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    RVA features The Beach Club at Anna Maria. Old Florida charm meets modern, designer-decorated decor at this private, un- ...

    From $100 per night (USD)

    VRBO

    Details
  • A Wright Place
    From $120 per night (USD)

    VRBO

    A Wright Place

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    MUST BOOK DIRECT TO USE PROMO CODES EARLY BLACK FRIDAY DEALS- book any stay for at least 7 nights in January 2022 and r ...

    From $120 per night (USD)

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  • LAY-Z LIV-N - 13
    From $86 per night (USD)

    VRBO

    LAY-Z LIV-N - 13

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    This TOTALLY REMODELED UNIT is located on the 2nd floor end unit is a 2 minute walk to the inviting sands of the Gulf be ...

    From $86 per night (USD)

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  • Runaway Bay Condo #203
    From $71 per night (USD)

    VRBO

    Runaway Bay Condo #203

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Beautiful furnished, completely updated, 2 BR / 2 BA condo in Runaway Bay, Anna Maria Island (#203). This gorgeous vaca ...

    From $71 per night (USD)

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    Details
  • Windshore A
    From $232 per night (USD)

    VRBO

    Windshore A

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Built new in 2011, Windshore A leaves no wishes open when it comes to your vacation on Anna Maria Island. Within walking ...

    From $232 per night (USD)

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    Details
  • Sandy Pointe II
    From $110 per night (USD)

    VRBO

    Sandy Pointe II

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Detta är en ljus och ljus 2-sovrum / 2 badrum Condo som ryggar upp till de vackra och fridfulla mangroverna (naturskydd) ...

    From $110 per night (USD)

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  • Runaway Bay 135
    From $129 per night (USD)

    VRBO

    Runaway Bay 135

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    SHORT WALK TO THE BEACH!! FIRST FLOOR CORNER PET FRIENDLY CONDO! Welcome to your Anna Maria Island Paradise! Featu ...

    From $129 per night (USD)

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  • Sunset Beach 103.77th
    From $302 per night (USD)

    VRBO

    Sunset Beach 103.77th

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to Sunset Beach House just a few steps away from the Gulf beaches of Anna Maria Island. Sunset Beach is a 4 bed ...

    From $302 per night (USD)

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    Details
  • Bungalow 108: The Dolphin Courtyard Bungalow
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    Bungalow 108: The Dolphin Courtyard Bungalow

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    A charming 1 bedroom bungalow complete with a full kitchen, queen size bed, queen sleeper sofa, and jacuzzi jet bathtub ...

    Click For Pricing

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    Details
  • Bungalow 106: The Sand Dollar Gulf Front Studio
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    Bungalow 106: The Sand Dollar Gulf Front Studio

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Spacious studio style bungalow with a full kitchen, king size bed, pull out sleeper sofa and a single shower bathroom. N ...

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  • Bliss & Tonic Up
    From $157 per night (USD)

    VRBO

    Bliss & Tonic Up

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This property is thoroughly cleaned and sanitized prior to your arrival. We pay special attention to high touch areas li ...

    From $157 per night (USD)

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    Details
  • Three Pines
    From $150 per night (USD)

    VRBO

    Three Pines

    Bedrooms:
    2.5
    Bathrooms:
    2
    Sleeps:
    5

    Sit back, relax and enjoy the breathtaking views from this cozy, vintage, beachfront cottage. This Old Florida style uni ...

    From $150 per night (USD)

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    Details
  • Sunset 156
    From $75 per night (USD)

    VRBO

    Sunset 156

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    This lovely condo offers the Gulf of Mexico across the street (west) and Palma Sola Bay (east) of property with pier for ...

    From $75 per night (USD)

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    Details
  • Southern Belle 111.Beach
    From $242 per night (USD)

    VRBO

    Southern Belle 111.Beach

    Bedrooms:
    5.5
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to Southern Belle Beach House located just steps away from the Gulf beaches of Anna Maria Island. Southern Belle ...

    From $242 per night (USD)

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  • One Shell Cove
    From $109 per night (USD)

    VRBO

    One Shell Cove

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The HOA has a 20 lb weight limit on dogs. STUDIO WITH ONE BATH QUEEN BED. S DIRECTLY ON THE BEACH- RIGHT ON THE SA ...

    From $109 per night (USD)

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    Details
  • Bluefin Cottage 108.75th
    From $119 per night (USD)

    VRBO

    Bluefin Cottage 108.75th

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Bluefin Cottage located a few houses from the Gulf beaches of Anna Maria Island. Bluefin Cottage is a half d ...

    From $119 per night (USD)

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    Details
  • Cozy Cabana West
    From $235 per night (USD)

    VRBO

    Cozy Cabana West

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Renovated in 2015, 2 bed 2 bath Villa perfect for families, couples or a small group of friends. The villa is located in ...

    From $235 per night (USD)

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    Details
  • Buddy's Beach House
    From $300 per night (USD)

    VRBO

    Buddy's Beach House

    Bedrooms:
    2.5
    Bathrooms:
    2
    Sleeps:
    5

    Welcome to Buddy's Beach House. A beachy chic getaway just 2 blocks to the beach. Stroll to the beach with a beverage in ...

    From $300 per night (USD)

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    Details
  • Lake By The Beach
    From $230 per night (USD)

    VRBO

    Lake By The Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    The Lake by the Beach at 6806 Palm Drive offers the best of both worlds! This beautiful two bedroom, two bath home is si ...

    From $230 per night (USD)

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    Details
  • Runaway bay unit 234 beach
    From $105 per night (USD)

    VRBO

    Runaway bay unit 234 beach

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    This one bedrooms sleep up to 4 people and the unit is equipped with a full kitchen and the utensils if you need to pre ...

    From $105 per night (USD)

    VRBO

    Details
  • Bungalow 105: The Seagull Gulf Front Studio
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    VRBO

    Bungalow 105: The Seagull Gulf Front Studio

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Spectacular gulf front views from nearly anywhere in the “Seagull” make this comfortable bungalow your personal tropical ...

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  • Beachside
    From $235 per night (USD)

    VRBO

    Beachside

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    VRC16-000521 Beachside is thoroughly cleaned and sanitized prior to your arrival. We pay special attention to high tou ...

    From $235 per night (USD)

    VRBO

    Details
  • Beach Breeze East
    From $90 per night (USD)

    VRBO

    Beach Breeze East

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to Beach Breeze East by RVA; a fantastic vacation rental for families or small groups that includes a spacious p ...

    From $90 per night (USD)

    VRBO

    Details
  • Sea Waves Cottage
    From $165 per night (USD)

    VRBO

    Sea Waves Cottage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Sea Waves cottage is located at north end of anna maria island. Brand new renovation, 3 bedroom with 2 bath room, with p ...

    From $165 per night (USD)

    VRBO

    Details
  • Bungalow 107: The Tortuga Courtyard Bungalow
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    Bungalow 107: The Tortuga Courtyard Bungalow

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    A cozy 1 bedroom bungalow complete with a full kitchen, queen size bed, queen sleeper sofa, and jacuzzi jet bathtub in i ...

    Click For Pricing

    VRBO

    Details
  • Stella Marina
    From $95 per night (USD)

    VRBO

    Stella Marina

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Stella Marina is a renovated and refurbished duplex suite with all modern new stainless steel appliances: over the stov ...

    From $95 per night (USD)

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    Details
  • Mangroves
    From $64 per night (USD)

    VRBO

    Mangroves

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Enjoy quiet sunsets from your private screened balcony at this two bedroom two bathroom third floor condo with preserve ...

    From $64 per night (USD)

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    Details
  • The Beach House
    From $270 per night (USD)

    VRBO

    The Beach House

    Bedrooms:
    2.5
    Bathrooms:
    3
    Sleeps:
    6

    Idyllic Holiday Properties is a small friendly holiday company offering an honest and efficient service for our privatel ...

    From $270 per night (USD)

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    Details
  • Sea Breeze Cottage
    From $140 per night (USD)

    VRBO

    Sea Breeze Cottage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Sea breeze cottage is located at north end of anna maria island. Brand new renovation, 2 bedroom with 2 bath room, with ...

    From $140 per night (USD)

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  • Anchors West
    From $120 per night (USD)

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    Anchors West

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    4

    Anchors West, located in a quiet and convenient location. Whether you want to stroll to the beach or to shopping and re ...

    From $120 per night (USD)

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  • Green Sand Castle
    From $334 per night (USD)

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    Green Sand Castle

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Beautiful, decorated 1700 sf home with vaulted ceilings, luxurious furnishings and open plan entertaining. Accommodates ...

    From $334 per night (USD)

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  • Tiki
    From $299 per night (USD)

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    Tiki

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Under Renovation- New Pictures coming soon! The Tiki, located at 3214 Gulf Drive in Holmes Beach is a spectacular three ...

    From $299 per night (USD)

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  • Breakers 3
    From $360 per night (USD)

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    Breakers 3

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    VRC20-000178 Breakers 3 is thoroughly cleaned and sanitized prior to your arrival. We pay special attention to high tou ...

    From $360 per night (USD)

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  • Runaway Bay -1st floor, 1Bedrm
    From $105 per night (USD)

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    Runaway Bay -1st floor, 1Bedrm

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This condo first floor (US), ground floor (UK)has had major improvements! The condo was completely remodeled in 2013 inc ...

    From $105 per night (USD)

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  • Breakers 1
    From $375 per night (USD)

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    Breakers 1

    Bedrooms:
    3.5
    Bathrooms:
    3
    Sleeps:
    8

    VRC16-000530 Breakers 1 is thoroughly cleaned and sanitized prior to your arrival. We pay special attention to high to ...

    From $375 per night (USD)

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  • Paradise Beach - East
    From $75 per night (USD)

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    Paradise Beach - East

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Stay at your own piece of tropical paradise by the beach and centrally located on Anna Maria Island. This island cottage ...

    From $75 per night (USD)

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  • Anna Maria Island Beach Paradise 5
    From $150 per night (USD)

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    Anna Maria Island Beach Paradise 5

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    An addendum to our cancellation policy: If the governor of Florida issues a Florida travel ban you will receive a refund ...

    From $150 per night (USD)

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  • Shell Cove 9
    From $160 per night (USD)

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    Shell Cove 9

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Shell Cove Condominium 9, located at 2310 Gulf Drive in Bradenton Beach, is a two bedroom, one bath Gulf front unit that ...

    From $160 per night (USD)

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  • Anna Maria Island Beach Palms 6B
    From $115 per night (USD)

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    Anna Maria Island Beach Palms 6B

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    An addendum to our cancellation policy: If the governor of Florida issues a Florida travel ban you will receive a refund ...

    From $115 per night (USD)

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  • Beach Bungalow - W
    From $69 per night (USD)

    VRBO

    Beach Bungalow - W

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Vacation to the perfect spot on Anna Maria Island! This two bathroom, two bathroom condo is only steps away from the bea ...

    From $69 per night (USD)

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  • LAY-Z LIV-N - 12
    From $86 per night (USD)

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    LAY-Z LIV-N - 12

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This 2nd floor end unit is located just one block east of the inviting sands of the Gulf beaches of Anna Maria Island i ...

    From $86 per night (USD)

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  • Lime Kiss Unit A
    From $154 per night (USD)

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    Lime Kiss Unit A

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to LimeKiss, Unit A! This stunningly decorated 3 bedroom, 2 bathroom duplex rental home located steps to the bea ...

    From $154 per night (USD)

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  • LAY-Z LIV-N - 8
    From $75 per night (USD)

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    LAY-Z LIV-N - 8

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    This is a 2nd floor unit with stair access only. You'll be drawn right in by this cozy 1 bedroom, 1 bathroom condo. It' ...

    From $75 per night (USD)

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  • Runaway Bay 235
    From $129 per night (USD)

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    Runaway Bay 235

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    2 BEDROOM 2 BATH CONDO WITH POND VIEW AND EASY ACCESS TO THE BEACH. Needing a beach fix? Just moments from the wh ...

    From $129 per night (USD)

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  • Sea Pirate 3
    From $125 per night (USD)

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    Sea Pirate 3

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Sea Pirate Condo #3, located at 3301 Gulf Drive in the heart of Holmes Beach is just a stone's throw from the tropic tea ...

    From $125 per night (USD)

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  • Beach Bungalow - E
    From $69 per night (USD)

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    Beach Bungalow - E

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Vacation to the perfect spot on Anna Maria Island! This two bathroom, two bathroom condo is only steps away from the bea ...

    From $69 per night (USD)

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    Details
  • The Beach Club At Anna Maria #6
    From $100 per night (USD)

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    The Beach Club At Anna Maria #6

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    RVA features The Beach Club at Anna Maria. Old Florida charm meets modern, designer-decorated decor at this private, un- ...

    From $100 per night (USD)

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  • Starfish Shack 7504.Gulf
    From $119 per night (USD)

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    Starfish Shack 7504.Gulf

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    5

    Welcome to the Starfish Shack located just a few houses from the Gulf beaches of Anna Maria Island. The Starfish Shack i ...

    From $119 per night (USD)

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  • Runaway Bay 102
    From $107 per night (USD)

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    Runaway Bay 102

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    1BR/1 BA pond view pet-friendly condo with great upgrades to kitchen and bath. Tile floors throughout the condo. Enjoy y ...

    From $107 per night (USD)

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  • The Beautiful Cove - Luxury 2 bed 2 bath apartment close to beach and amenities
    From $100 per night (USD)

    VRBO

    The Beautiful Cove - Luxury 2 bed 2 bath apartment close to beach and amenities

    Bedrooms:
    2.5
    Bathrooms:
    2
    Sleeps:
    4

    Denna vackert dekorerade lägenhet i 2019 ligger i en lugn, privat miljö bland ön Anna Maria, och bara en kort promenad f ...

    From $100 per night (USD)

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  • Luxury 4 Bed Beachfront Home
    From $250 per night (USD)

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    Luxury 4 Bed Beachfront Home

    Bedrooms:
    5.5
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to 'Sky way view', one of the most exclusive homes on Anna Maria Island. It is located in one of the most specta ...

    From $250 per night (USD)

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  • Twin Palms Beach Retreat
    From $258 per night (USD)

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    Twin Palms Beach Retreat

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    **We Want You To Feel Like You've Got Friends with a Beach House** Come stay in the home of a New York Times best-selli ...

    From $258 per night (USD)

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  • Franks Beach House
    From $288 per night (USD)

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    Franks Beach House

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    We have found our perfect spot on the beach. After visited the resorts and beaches of Florida for many years we are here ...

    From $288 per night (USD)

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  • Gulf-View-Paradise
    From $220 per night (USD)

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    Gulf-View-Paradise

    Bedrooms:
    3.5
    Bathrooms:
    3
    Sleeps:
    6

    Det fullt luftkonditionerade huset ligger i ett lugnt, exklusivt bostadsområde på spetsen av ön. Mile vita sandstranden ...

    From $220 per night (USD)

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  • SEATURTLES COVE  LUXUS CONDO
    From $25 per night (USD)

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    SEATURTLES COVE LUXUS CONDO

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    5

    2015 nyrenoverade och fullt utrustade fritidshus ligger på ön Anna Maria i Holmes Beach-distriktet i ett lugnt och välsk ...

    From $25 per night (USD)

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  • Sand Dollar Cottage
    From $190 per night (USD)

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    Sand Dollar Cottage

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    The small beach cottage is located in a quiet, exclusive residential area on the tip of the island. A 60-meter walk to t ...

    From $190 per night (USD)

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  • Four Beach Lovers Unit 3
    From $330 per night (USD)

    VRBO

    Four Beach Lovers Unit 3

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    ATTENTION: We rent with 1 week minimum: Saturday to Saturday Old Florida Feeling: bungalow right on the beach on level - ...

    From $330 per night (USD)

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  • Beach-Boat-Bay-Paradise
    From $260 per night (USD)

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    "Beach-Boat-Bay-Paradise"

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    This beautifully spacious house stands on a very large property right on the water at the northern tip on AMI. The house ...

    From $260 per night (USD)

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  • Bradenton Beach Club 251
    From $171 per night (USD)

    VRBO

    Bradenton Beach Club 251

    Bedrooms:
    3.5
    Bathrooms:
    3
    Sleeps:
    6

    Bradenton Beach Club 251 - 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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  • Magnolia Bleu
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    Magnolia Bleu

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    8

    Magnolia Bleu House and Cottage is a stunning new property that does not disappoint. With 3 bedrooms and 2 baths in the ...

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