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Holiday Rentals in Anna Maria Island, FL

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    ₹ 13,550 Average
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    Travellers to Anna Maria Island are booking December dates now. Secure your holiday home today, and have the perfect trip.
    1 / 24
    4.5 of 5 stars (8) Very good
    Holmes Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Holmes Beach
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Holmes Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Anna Maria
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    This unit is a Wonderful Beach Vacation Spot ! It is fully furnished, with 2 TV's, Wi-Fi, Cable , pool, hot tub, Patio with 2 grills, directly on the BEACH - with fabulous Gulf of Mexico blue water. There is a 5 Star Zagat rated resturant on the property. There is twice weekly maid service and... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    1 / 29
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Come and stay at this newly renovated unit; one of two units available at this superb duplex located just 500 meter from beautiful Holmes Beach on Anna Maria Island. This spacious two bedroom two bathroom property can accommodate up to 6 persons with a queen-size bed in the master bedroom with... View all property information
    Location Information
    Anna Maria Island, Florida
    1 / 16
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.;  2 Bedroom, 2 Bath (sleeps 6) - 202 78th Street - Holmes Beach A perfect beach is one where all you need is a bottle of sunscreen and a towel. All you... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
    1 / 23
    Anna Maria
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    This quaint, old-Florida style rental is nestled in the north shore area of Anna Maria Island. Shabby chic style, located 2 blocks from the beach and 2 blocks from the bay! Only one block from Pine Ave., with its old-time feel with shops and salons. Steps from fine dining, the historic city pier,... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    1 / 24
    5 of 5 stars (2) Excellent
    Anna Maria
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    This is the vacation rental home of your dreams! This custom bay-front home on the north end of Anna Maria Island offers 3600 square feet of luxury accommodations and has all the fine touches and professional craftsmanship one would expect in a high-end custom home. When walking into this amazing... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    1 / 24
    Holmes Beach
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
    About this property
    Seabreeze Villa is a fabulous home for your vacation on Anna Maria Island. This beautiful Mediterranean designed home is located in central Holmes Beach, and is within walking distance of shopping, restaurants, and the white sand beach! This spacious home is equipped with a fantastic kitchen,... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
    1 / 12
    3 of 5 stars (1) Average
    Holmes Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Casa Del Mar is a 4 bedroom, 2.5 bath chic Key West style island home with a brand new heated swimming pool located in northern Holmes Beach. Designer decorated from top to bottom. Close to shopping, restaurants, and the trolley stop. Come and enjoy the island life at its very best! Sleeps upto 6-8... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
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    1 / 7
    Holmes Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • x
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    Only 2 houses away from the beautiful white sandy beaches of Anna Maria Island. This newly constructed Holmes Beach 2 bedrooms and 1- 1/2 bathroom house is over 2000 square foot with a heated private saltwater pool. Open floor plan, flat screen TV's, and two balconies overlooking the beach are... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
    1 / 17
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; 2 Bedroom, 2 Bath (sleeps 6) - 'Pisces Playground' - 205 73rd Street The open and airy duplex at 205 73rd Street gives you the space your family needs... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
    1 / 15
    Holmes Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Whoever said “you can’t have it all” never spent a week in this property.  This elevated, Mediterranean style private single family home is ideal for... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 12
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; 2 Bedroom, 2 Bath (sleeps 4) - 'Katie's Beach Bungalow' - 108 8th Street So., Bradenton Beach This elevated, rental beach house is constructed in the... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island
    1 / 24
    Anna Maria
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; (3) Bedroom, (2) Bath (Sleeps 6) – “Sugar Plum Hideaway East”- 114 Mangrove East in Anna Maria You’ll be pleased when you reserve Anna Maria Island... View all property information
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    Anna Maria, Anna Maria Island
    1 / 18
    Holmes Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Elegant and tropical poolside paradise holiday rental. (4) Bedroom, (3.5) Bath, accommodates to (12) people: (2) Kings, (1) Queen, (4) Twin Bunks, (1) Queen... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
    1 / 63
    3 of 5 stars (2) Average
    Bradenton Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Private Outdoor...
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    • x
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    • x
    About this property
    January Special Offer $2350.00 All-Inclusive. Save $1195.00. Anna Maria Island is not a place you go to the beach. When you are on Anna Maria Island you are at the beach. Welcome to paradise. Featured here is a gorgeous new 4 bedroom 3 bathroom home providing you with uncompromising luxury beyond... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island
    1 / 11
    Anna Maria
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Chic and cozy vacation rental nestled right between the Tampa Bay and the Gulf of Mexico.   (2) Bedroom, (1) Bath, accommodates up to (6) people: 1 Queen, 2... View all property information
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    Anna Maria, Anna Maria Island
    1 / 30
    Anna Maria
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; 5 Bedroom,  3 Bath (sleeps 10) - "Au Soleil" - 717 Jacaranda, Anna Maria We don’t have high rise hotels on our island and with holiday rentals like Au... View all property information
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    Anna Maria, Anna Maria Island
    1 / 14
    Anna Maria
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Living at the beach is like living anywhere else except it’s better in almost every way imaginable. Experience it for yourself in 208 Periwinkle with all the... View all property information
    Location Information
    Anna Maria, Anna Maria Island
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    1 / 15
    3 of 5 stars (3) Average
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Balcony
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    • x
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    • x
    About this property
    Sunset Terrace - Condo 2 Bedroom/ 2 Bath , maximum occupancy of 4 people. What a view! This lovely top floor condo sits directly on the Gulf of Mexico with a full view of the water from the kitchen/dining, living room and the 20 foot lanai. Sleep and awake to the sounds of the surf. The beach... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island
    1 / 19
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Wi-Fi
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    • Pet-friendly
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    • x
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    • x
    About this property
    Beautiful condo on ground level 75 steps to Bradenton Beach !! Runaway Bay has been voted best resort on Anna Maria Island. There are 2 bedrooms, a master with king bed with a new mattress. second bedroom has twin beds new mattresses. There are 2 bathrooms one located by each bedroom. The... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island
    1 / 15
    Holmes Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.;   Refreshing and tropical are the perfect ways to describe this vacation rental home Mango Breeze at 141 50th Street! Spend a week here in Holmes Beach and... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
    1 / 15
    Anna Maria
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Grant's View is a private bay front home is located on the Tampa Bay where you will enjoy the amazing endless views of the open water, not to mention... View all property information
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    Anna Maria, Anna Maria Island
    1 / 26
    Anna Maria
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; This newly remodeled and updated island vacation rental duplex is just a stroll to the Gulf of Mexico and our beautiful sunsets. (3) Bedroom, (2) Bath,... View all property information
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    Anna Maria, Anna Maria Island
    1 / 17
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; This two bedroom, two bath Direct gulf frontvacation condo gives room for four guest to enjoy the Gulf waves crash in the distance while a little bit closer... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
    1 / 15
    3 of 5 stars (1) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Washer
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    • x
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    • x
    About this property
    BEACHCOMBER, just 200ft from 7 miles of white sandy beach, is a beautifully furnished cottage with 2 bedrooms, 1 double and 1 twin. The master bedroom has an en-suite bathroom. There is also a 2nd bathroom with shower, WC and basin only. A large open plan living room, kitchen, dining room leads... View all property information
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    Anna Maria Island, Florida
    1 / 20
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    A beautiful condo in stunning grounds for your next Florida vacation. Unit 127 at Runaway Bay Resort gives you all the amenities that you need for a wonderfully relaxing vacation on beautiful Anna Maria Island. The fully furnished 2 bedroom, 2 bath condo includes free high speed wireless internet,... View all property information
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    Bradenton Beach, Anna Maria Island
    1 / 24
    Anna Maria
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Periwinkles are small, sunshine loving flowers with a color so distinct they name crayons after it. On a street baring their name in Anna Maria Island,... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    1 / 13
    Holmes Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Key Lime Cottage East, 3 bedroom 2 bath new duplex with private heated pool.  Sleeps up to 6. Key Lime Cottage East welcomes you to this recently re-done... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 30
    Anna Maria
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.;   Harmony House is such a special place! Remember days gone by in this Key West style holiday rental with a c'ocktail-style' sparkling pool in a tropical... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    1 / 41
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    ** Call +1 908 236 2966 to inquire about this property Island Paradise is just that - the best view on Anna Maria Island. Panoramic views of the beautiful blue waters of the Gulf of Mexico and the white sand beaches. And don't forget the legendary sunsets. It simply does not get any better than... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 12
    Bradenton Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Includes swimming pool and partial views of the gulf, and only 1/2 block from the incredible beaches, this adorable vacation rental in Bradenton Beach comes... View all property information
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    Bradenton Beach, Anna Maria Island
    1 / 17
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; On Anna Maria Island, you hear a lot about visitors experiencing love at first sunset. By the time sun is setting on your first day, most people are hooked.... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 34
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    West Bay Cove 222 - Condo 2 Bedroom/ 2 Bath , maximum occupancy of 6 people. West Bay Cove is a great location for taking advantage of everything that Anna Maria Island has to offer. Only a block from the public beach area, close to the grocery store, several shops and at a trolley stop, this... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 16
    Holmes Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; 3 Bedroom, 2.5 Bath (Sleeps 6) - “Palm Gables” 106 36th Street in Holmes Beach. Enjoy the gulf front Anna Maria Island vacation you deserve when you... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 24
    Holmes Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Come and stay in Holmes Beach at this contemporary, custom, elevated, single family home with spectacular Bimini Bay frontage. This magnificent home has all the bay-front views you would ever want from almost every room. This home was remodeled in 2013 to include a great open floor plan with 3,676... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 12
    Bradenton Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Enjoy a beautifully remodeled Anna Maria Island home with a taste of history. This 3 bedroom/3.5 bath home was once the center for AMI's phone services. Make this landmark home part of your ultimate family vacation retreat. Enjoy an ocean view from the ground floor as well as from a large upper... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island
    1 / 24
    Anna Maria
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; 4 Bedroom, 2 Bath (sleeps 8) - 'Blue Heron Beach House' - 117 Peppertree Lane in Anna Maria.  Welcome to “Blue Heron Beach House”! This adorable Anna Maria... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    1 / 70
    4 of 5 stars (1) Very good
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Special Offer Sept. 1-Oct. 30 $1000.00 all-inclusive for a one week rental save $782.50. Anna Maria Island is not a place you go to the beach. When you are on Anna Maria Island you are at the beach.The Anna Maria Island 'Beach Paradise Condo' is located on Holmes Beach directly in the middle of... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 21
    Anna Maria
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Located on beautiful Anna Maria Island, "Le Paradis" (which means Paradise in French) is just a short stroll to the sugar white sand beaches of beautiful Anna Maria Island... Experience a luxurious beach vacation with over 2100 hundred square feet of tastefully living space with an expansive... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    1 / 10
    Anna Maria
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; The various shades of blue throughout Sea's the Day make this a  water lover's dream vacation cottage. Sitting about 200 steps to the beach access, it's like... View all property information
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    Anna Maria, Anna Maria Island
    1 / 9
    Anna Maria
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Just steps to the beach! This charming 1 bedroom, 1 bath apartment is situated above the garage and has a large open deck with views of the Gulf. Small kitchen with separate living room and bedroom. Queen bed and a twin bed and full size sleeper sofa. Sleeps 4 MAX. Washer/Dryer available.... View all property information
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    Anna Maria, Anna Maria Island
    1 / 18
    Bradenton Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Includes swimming pool and partial views of the gulf, and only 1/2 block from the incredible beaches of Anna Maria Island, this adorable vacation rental in... View all property information
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    Bradenton Beach, Anna Maria Island
    1 / 14
    Bradenton Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
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    Welcome to Anna Maria Island and the City of Bradenton Beach.<BR><BR>We are located 45 minutes south of St Petersburg, an hour south of the Tampa International airport, 2 hours from Orlando and its many theme parks and twenty minutes north of Sarasota on the Gulf side of Florida.<BR><BR>Our island... View all property information
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    Bradenton Beach, Anna Maria Island
    1 / 24
    Bradenton Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; 3 Bedroom, 2.5 Bath (Sleeps 6) – “South Beach Village” – 111 10th Street in Bradenton Beach When you arrive to “111 South Beach Village”, located at 10th... View all property information
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    Bradenton Beach, Anna Maria Island
    1 / 17
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Sunset Villa awaits the vacationer in you. Located in this well-kept condo complex directly across front the street from the best beaches on the West coast... View all property information
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    Bradenton Beach, Anna Maria Island
    1 / 10
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Idyllic and beachy direct gulf front seasonal rental. (2) Bedroom, (2) Bath, accommodates up to (4) people: 1 King, 2 Twins. Shared heated pool and spa,... View all property information
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    Bradenton Beach, Anna Maria Island
    1 / 12
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
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    AN IDEAL FAMILY REUNION LOCATION - Close to everything on the island!<BR><BR>Alecassandra Vacation Villas on Anna Maria Island, Florida<BR><BR>Villa #4, 2 Bedroom, 2 Bath, Sleeps 6<BR>Queen Bed, Master; <BR>Queen Bed, Guest Bedroom; <BR>2 Twin Beds, Guest Bedroom; <BR>Queen Sleeper Sofa, Living... View all property information
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    Bradenton Beach, Anna Maria Island
    1 / 8
    5 of 5 stars (1) Excellent
    2 Bedrooms, 4 Bathrooms, Sleeps 4 | Quick View
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    • Terrace
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    Location Information
    Anna Maria Island, Florida