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    Travellers to Anna Maria Island are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    571 Matching Rentals in Anna Maria IslandView all 2,284 rentals
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    Gulf Front Guest House1 / 15
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Beautiful, decorated and furnished, spacious Great Room family & kid friendly,1 / 37
    (43)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    BoatHouse Cottage - N. end Anna Maria- Private Pool- NEWLY REMODELED BATHROOM!1 / 16
    (41)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Beautiful AMIBeachClub north end elevated pool home. Minutes walk to the Gulf.1 / 32
    (46)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    North End of AMI- Ground Level Family Friendly updated home1 / 39
    (39)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Best Location on Island -  Read Our Guest Reviews!1 / 23
    (80)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Anna Maria, Anna Maria Island 34216
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Classic Anna Maria 2 Family Home With Pool/Jacuzzi And Gazebo Across From Beach1 / 23
    (28)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Anna Marie Hideaway!1 / 36
    (21)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Waterfront Private Island Escape w/ Guest House Bayside Dock - Beach blocks away1 / 25
    (26)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    Beautiful, Ocean-Front Home with Golf Cart & Bikes--Halcyon House1 / 24
    (113)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Charming Cottage! Quiet North- End Oasis, Steps To Bay And Gulf. Heated Pool.1 / 22
    (39)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    BayView and Access, North End Modern Luxury 3/3 Home, Heated Pool, Cabana W/TV1 / 50
    (71)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Desirable North End, Steps to the Best Beach, 2/2 Luxury Cottage/Heated Pool!1 / 50
    (56)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Beachfront Oasis ~ Luxury & Spectacular Beachfront Views1 / 50
    (24)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    NorthEnd Luxury 2/2 Cottage, Bay View-Beach Access, Heated Pool, Cabana w/TV1 / 50
    (63)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Angel Fish Cottage - Steps to Beach - Private Heated Pool-REMODELED BATHROOM!1 / 21
    (48)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Classic Anna Maria 2 Family Home With Pool/jacuzzi And Gazebo Across From Beach1 / 23
    (11)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 1 Quick View
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 1
    Newly Built Pine Ave 2/2 Steps To Beach, Bay, Shops, Restaurants & Free Trolley!1 / 50
    (42)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Book NOW for 2017!  Exquisite Designer Beach Cottage, 3BR, 2BA1 / 18
    (42)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    No Streets to Cross to Anna Maria Beaches-Newly Remodeled 3 Bed/2 Bath Cottage1 / 50
    (31)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Charming beach getaway steps from the Gulf1 / 29
    (8)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Seas The Day- Charming Florida cottage on North End1 / 24
    (14)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Canal home on the North end.1 / 23
    (4)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Peppertree Paradise. A true gem! Beach block!1 / 24
    (10)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Anapauo Beachhouse-  Million dollar views of Tampa Bay!1 / 32
    (4)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Kingfish- North end family home on canal!1 / 42
    (23)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    Jersey Girl- Stunning home 1 block from Pine Ave.1 / 34
    (15)Excellent
    6 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 10
    Chillifish- Peaceful Floridian home.1 / 26
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Beach Haven- Premier property on North End1 / 31
    (7)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Terrace
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 8
    Tides Inn- Family home with tropical pool area.1 / 34
    (14)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Water front cottage, nestled between the mangroves, overlooking the Hammock Bayo1 / 29
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Angel Fish Cottage -  North End  - Steps to Gulf and Bay with Heated Pool1 / 18
    (48)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Casa Violeta. Just steps from the gulf!1 / 39
    (14)Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    ` Stunning Bay Front Villa`,Exclusive Construction1 / 41
    (18)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Stunning Bayfront New Contruction1 / 47
    (13)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    North end canal front  home . tiki hut, dock, heated pool, jacuzzi beaches....1 / 50
    (15)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Spacious Condo overlooking Anna Maria Sound1 / 36
    (13)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Holmes Beach, Anna Maria Island 34209
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    LOCATION .... LOCATION!!!  DISCOUNTED 10% NOVEMBER1 / 21
    (9)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Palm Perch... Newly renovated unit close to beach, shopping & restaurants1 / 13
    (29)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    FANTASTIC location!!!  Spacious 2 Bed/2 Bath Condo1 / 26
    (6)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Beach front/pool house, quiet, private,1 / 22
    (61)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    102-68th Street, Holmes Beach, Fl. (Unit #203)1 / 26
    (44)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 3 Quick View
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 3
    LOCATION, LOCATION!! DISCOUNTED 10% NOVEMBER!!1 / 30
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Gulf Sands 103, 2B/2B Beachfront condo on Anna Maria Island!1 / 22
    (46)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    ***SALE*** BUY 4 NIGHTS, GET 1 FREE. LUXURY 3/3 CONDO ON THE ANNA MARIA SOUND. V1 / 20
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Holmes Beach, Anna Maria Island 34209
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    THANKSGIVING WEEK SPECIAL!  Ground Level N End Luxury!1 / 50
    (23)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    THANKSGIVING WEEK SPECIAL! Charming N End 3/2 Cottage has it all!1 / 50
    (21)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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