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Holiday Rentals in Anna Maria Island

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    Travellers to Anna Maria Island are booking August dates now. Secure your holiday home today, and have the perfect trip.
    All 1,127 Rentals in Anna Maria Island
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    2104 Ave A -Private Home 2 Bedroom/ 2 Bath , maximum occupancy of 4 people. HUGE DISCOUNTS FOR THE LAST 2 WEEKS IN APRIL 2017! CALL NOW AND BOOK YOUR VACATION. This is a cute single family home located only minutes away from the popular BeachHouse Restaraunt (newly renovated), Bay Front Park,...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Custom built in 2013 this three bedroom, two bath home is beautifully designed for six guests. Come to Island Breeze and relax with all the amenities to make your vacation home a truly memorable experience. From your first step into the oasis you will feel yourself decompress. Eleven foot ceilings...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    6 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
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    "Grande Haven" - 804 North Shore Drive in the city of Anna Maria. Accommodating up to 16 guests, Anna Maria vacation rental home “Grande Haven” is a spectacular example of high architecture, fine design and custom finishing at its best! This luxury 6 bedroom 3 bathroom home was designed by the...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 16
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Welcome to the Anna Maria Island vacation rental you’ve been dreaming of! “Costa Lotta” has everything you would expect from a gold rated property plus a fantastic location. When you enter “Costa Lotta” you’ll know you have found the perfect vacation spot for relaxation and island style fun....
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Garden Villa #2 located at 303 42nd Street in Holmes Beach is a delightful island locale situated conveniently across from the Manatee Public Beach. Garden Villa units have recently undergone renovations for a fresh, tropical ambience. The surrounding property boasts an onsite coin operated laundry...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    BEACH NEST ***Pool*Hottub*Dock*Steps to Gulfside beach* Shelling*SPOIL YOURSELF!1 / 23
    (9)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Ahhhhhh. Welcome to Beach Nest! Ready to satisfy that oh-my-gosh-we-need-a-vacation? Kick off your shoes and throw them in the back of the closet. Promise yourselves to live in bathing suits from breakfast to bedtime! Vacationers, dreamers, honeymooners, would-be family-reunion planners and just...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    SAVE $400.00 5*WaterfrontCanal/Pool/Dock/Kayak/Bikes/Hammocks/Private/Family Fun1 / 45
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    SAVE $400.00 REGULAR SUMMER RATE FROM $2450.00 TO $2050.00 Adriel's Place in Anna Maria...located in upscale private golf club neighborhood, a stone throw from pristine beaches, restaurants and island entertainment ( less than 1 mile ). An expansive backyard dotted with majestic palms, papered...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    The Crow's Nest, located directly on the beach at 2416 Gulf Drive in Bradenton Beach is a unique three bedroom, two bath home that was designed by a man with a passion for boats and a love of the sea. From its lofty view, enjoy a perspective of Bradenton Beach from the spacious screened lanai that...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Coquina Sands, view beach from balcony, priv pool1 / 12
    (6)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    This is a gorgeous home, just 1/4 block from the beach which you can see from the balcony. Private elevator to all floors, relaxing living room with flat screen TV. Impressive Kitchen with granite counter tops, Stainless steel appliances, wood floors, bar sitting area, large dining room....
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Welcome to Palm Isle 3201 – a two bedroom, two bathroom vacation cottage in one of the most coveted complexes on Holmes Beach. The warm tile, coastal inspired décor, and ample sunshine make it feel like a cozy family home and you’ll love it like it was your own after a week of sleeping, sunbathing,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Seaside Beach House #101 located at 102 68th Street in Holmes Beach is a direct Gulf front complex with a heated pool at beachside. It’s one of the nicest complexes on Anna Maria Island. This "hidden away" property is located on a quiet side street in the northern end of Holmes Beach. The beach...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Gulf Sound is a gulf side, ground level tri-plex located at 2814 Gulf Drive in the southern end of Holmes Beach. This two bedroom one bath unit is fully equipped with everything you need for your stay. Each unit has been updated and is comfortably furnished. It's quiet, yet close to shopping,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    The extended Florida vacation spot you have been looking for is waiting at 516 77th Street! This great canal front Anna Maria Island vacation rental home offers a laid back spot for fishing, boating and enjoying time on the beach. This Holmes Beach rental is on a canal right off Bimini Bay and...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Bayview Condo E - Condo 2 Bedroom/ 2 Bath bay view, maximum occupancy of 4 people. Community pool. Magnificent Bay views are enjoyed from this elevated condo located on a quiet cul-de-sac in Bradenton Beach. This intimate 8 unit building is a brief two minute walk to the sugar sand beach on the...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Anna Maria Island's Castnetter 2, located at 1303 Gulf Drive South in Bradenton Beach is a delightful island locale offering breath-taking unobstructed views of the Gulf of Mexico. Castnetter 2 is conveniently located at the North entrance to the Coquina Public Beach and 1/2 mile from Historic...
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    Bradenton Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Gulf Sound is a gulf side, ground level tri-plex located at 2814 Gulf Drive in the southern end of Holmes Beach. This five bedroom, three bath property is fully equipped with everything you need for your stay. Each unit has been updated and is comfortably furnished. It's quiet, yet close to...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    3 Bedroom, 2.5 Bath (sleeps 6) - "La Casa Denton" – 7306 Gulf Drive La Casa Costiera unit 3 in Holmes Beach. Experience the Tropical beach paradise vacation of a life time when you stay at Holmes Beach vacation rental condominium “La Casa Denton”. This gorgeous beach front condo, located...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Seabreeze Cottage is coastal living chic at its best! This huge one bedroom, two bath cottage is located at 103 Highland Avenue in the historic Bridge Street neighborhood of Bradenton Beach. The gorgeous beach is just about 60 yards or so down a quiet street, turn the other way and you are at the...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Garden Villa #3 located at 305 42n Street in Holmes Beach is a delightful island locale situated conveniently across from the Manatee Public Beach. Garden Villa units have recently undergone renovations for a fresh, tropical ambience. The surrounding property boasts an onsite coin operated laundry...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    (4) Bedroom, (4) Bath (Sleeps 8) – “Beachy Blue”- 129 52nd St in Holmes Beach. “Beachy Blue” is a magnificent Anna Maria Island vacation home that will make your vacation feel truly luxurious! This spacious rental home offers accommodations for up to 8 guests including 4 roomy bedrooms with 1...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    The Lake by the Beach at 6806 Palm Drive offers the best of both worlds! This beautiful two bedroom, two bath home is situated on a spring fed lake yet it's only three blocks to the beach. New renovations include a brand new family room addition with easy access to the beautiful pool! A unique...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    The Absolutely Perfect Beach House, located at 3009 Avenue F in Holmes Beach is just that – absolutely perfect! This spectacular four bedroom, three and one half bath gulf front home with an extra media room. It has its own private beach and heated pool has just been built. This beautiful home is...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Views, views, views! You will love watching the waves and the sunset over the sandy Gulf beach—one hundred steps away—as well as the boats and the sunrise over the Bay. Located at 102 6th Street South in Bradenton Beach, this beautiful and comfortable beach property is an easy walk to historic...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    The cottages at Palm Isle Village are some of the finest and most favored vacation properties on Anna Maria Island. We are always very proud to recommend them to our vacationers and no one can say it isn’t a special place to spend quality time with friends and family. Widow watches surround the...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Holmes Beach vacation rental “Rest Assured” is a fun tropical inspired ground level home comfortably accommodating up to 8 vacationers. Located in beautiful Holmes Beach, “Rest Assured” has 3 bedrooms, a den and 2.5 bathrooms with 2 King beds, 1 Queen bed and 2 twins in the den. Tastefully designed...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ss Salamander North ~ RA1445681 / 21
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Welcome to the SS Salamander, North unit at 121 50th Street in Holmes Beach. This recently updated two bedroom and one and one half bath unit is just a one block stroll down a side street to the beautiful white, sandy beaches. It’s located in a quiet and preferred residential neighborhood yet it's...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Down by the Sea is a lovely ground level vacation rental home in a quiet Anna Maria City neighborhood. Beautiful tropical setting with a brand new heated salt water pool. (3) Bedroom, (2) Bath, accommodates up to (6) people: 1 King, 1 Queen, 2 Twins. Lovingly and locally decorated to make you feel...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    The Beachcomber, located at 3306 4th Avenue in Holmes Beach is the ideal, dream vacation home. This recently built gulf front home features a heated salt water pool and spa nestled in a tropical setting. It does not get any better than this! Luxurious furnishings, an elevator, a gourmet kitchen, a...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Updated 2 bedroom townhouse condo in Bradenton Beach with an unobstructed view of the Gulf of Mexico. Grab your beach chairs, umbrella, cooler and towels (provided) cross Gulf Drive and you're on the beach in a minute. If your enjoy fishing, the pier extending out into the Gulf is a great place to...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    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 get the taste of island life on your tongue. Spend a beach holiday on Anna Maria Island in 2,500 feet of style and luxury. There’s room for the...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Enjoy your own slice of island life with a week at 25 Seaside Court!  (2) Bedrooms, (2) Bathrooms, accommodates up to (4) guests. 1 Queen, 2 Twins. Highspeed internet, pets welcome with fee, bay front location with boat access, not far from the beach. Located in a quiet but vibrant neighborhood...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    The Good Times Upstairs Unit A, located at 303 Highland Avenue in Bradenton Beach is a quiet, two bedroom, and two bath unit with a spacious living room, large open design European kitchen and very spacious open deck. Just one very short block to the beach, the unit provides the ultimate in...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    The Good Times Downstairs Unit B, located at 303 Highland Avenue in Bradenton Beach is a quiet, two bedroom, and two bath unit with a spacious living room, large open design European kitchen and very spacious open deck. Just one very short block to the beach, the unit provides the ultimate in...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Sunseeker Haven located at 302 24th St North Unit B in Bradenton Beach is a light, bright upscale two bedroom two bathroom vacation getaway. It is nestled between beautiful Anna Maria Sound and the turquoise Gulf waters. Enjoy the entire spacious upper floor of the two unit condo. You have French...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Beachside Palms 2 located at 4104 4th Avenue in Holmes Beach is a delightful island locale located directly across the street from the seven acre Manatee Public Beach and the Gulf of Mexico. This beautiful and totally renovated two bedroom unit with one bath sleeps six with a queen size bed in the...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    West Bay Point Moorings 42 - Condo 2 Bedroom/ 2 Bath , maximum occupancy of 6 people. Relax and enjoy the tranquility of West Bay Point Moorings with its community of waterfowl, splashing dolphins and slow moving pleasure boats while taking in the panoramic view of Tampa Bay. Your vantage point...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Anna's Cottage, located at 105 3rd Street South in Bradenton Beach is a historic beach cottage located across the street to the emerald green water of the Gulf of Mexico. This refurbished cottage features a new kitchen,a new third bedroom and bathroom. A large screened in patio in the backyard with...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Waters Edge Unit 106S, located at 5806 Gulf Drive in the northern end of Holmes Beach, is a beautifully updated and spacious one bedroom, one and one half bath unit in a popular Gulf front complex. This unit offers every imaginable amenity to make your Anna Maria vacation a pleasure! The popular...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Gulf Sound is a gulf side, ground level tri-plex located at 2814 Gulf Drive in the southern end of Holmes Beach. This one bedroom one bath unit is fully equipped with everything you need for your stay. Each unit has been updated and is comfortably furnished. It's quiet, yet close to shopping,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Beachside Palms 1, located at 4104 4th Avenue in Holmes Beach is a delightful island locale located directly across the street from the seven acre Manatee Public Beach and the Gulf of Mexico. This beautiful and totally renovated two bedroom unit with one bath sleeps six with a queen size bed in the...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Island Beach Club 2 - Condo 2 Bedroom / 1.5 Bath ground level gulf front , maximum occupancy of 4 people. Community pool. Your Ultimate Gulf Front Luxury Vacation! Look no further. You will love this ground level 2 bedroom/1.5 bath condo. This spectacular, brand new Island Beach Club luxury...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    8 Bedrooms, 8 Bathrooms, Sleeps 24 Quick View
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    Seagrass Flats Condo is a four unit complex located at 101 25th Street North in Bradenton Beach that features a large heated pool and bbq area. Immediately across from the beach, you can be on the sand in less than one minute. It’s a perfect vacation retreat for large family get- togethers and...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 8 Bedrooms, 8 Bathrooms, Sleeps 24
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Paradise Found at this Anna Maria Island canal front pool home with private dock. Located just 3 blocks from the beach, this spacious and recently renovated home boasts two master suites and comfortably sleeps eight. Just steps to free island trolley and two blocks from shops and restaurants. Other...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    4 Bedroom, 3.5 Bath (Sleeps 8) - “Mango Tango” - 145 50th Street in Holmes Beach. Experience a tropical memory maker vacation of a lifetime when you visit “Mango Tango”! This four bedroom home accommodating up to 8 guests is a lovely place to unwind with family and friends on tropical Anna Maria...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    The Nantucket1 / 27
    (19)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    3 Story 'Nantucket' Style - 4 bedroom/ 3 bath villa is just a short walk to the beach - Nestled in a tropical setting, only a few blocks to the Gulf beach; private pool great for cooling off and a large sun deck. 4 Bedrooms/3 baths, large master suite with king size bed and a roman tub, 2nd...
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Luxury is here in this brand new direct gulf front three bedroom and three full bath Anna Maria island luxury holiday rental. Relax your cares away in the master suite fit for royalty, dual headed shower with massage jets and a Jacuzzi tub. Each bedroom has it's own private bath.Outdoor living at...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    This 3 bedroom 2 bath home is on the north end of Anna Maria Island and can be combined with Pirate Cove (a separate building ) to make a 5 bedroom beach front vacation home. All bedrooms in Hooks Haven are Queen size. Two bedrooms are on the main floor and one is on the second floor. Spiral...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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