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Anna Maria Island Vacation Rentals

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    Travelers to Anna Maria Island are booking December dates now. Secure your vacation rental today, and have the perfect trip.
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    6 Bedrooms, 4 Bathrooms, Sleeps 16 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. New and modern throughout, Sans Souci offers two complete units with three bedrooms, two baths each. The master bedroom has a king...
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    Bradenton Beach, Anna Maria Island 34217
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 16
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    The Anna Cabana Beach House is an adorable two bedroom, two bath home located at 3709 Gulf Drive in Holmes Beach. This quaint home has a large open deck with a great view of the beach. Watch the sunsets or enjoy the tropical landscaping on the large deck facing the Gulf. Numerous fruit trees and...
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    Holmes Beach, Anna Maria Island 34218
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    New Heron: 2BR "Perfect Spot" a Block from Beach1 / 23
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Just one short block away from the pristine water of the Gulf of Mexico and Anna Maria Island's gleaming white sand beaches, this two-bedroom, one-bath vacation rental has been updated inside and out for your vacationing pleasure. A well-appointed kitchen and outdoor grill may entice you to create...
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    Holmes Beach, Anna Maria Island 34217
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Tiki Tides located at 6250 Holmes Boulevard in North Beach Village is a beautiful townhome in the heart of Holmes Beach. This property has been recently updated in a cute and beachy decor and has everything you need to enjoy Anna Maria Island. You are just a few steps away from the heated community...
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    Holmes Beach, Anna Maria Island 34217
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    The Heron unit at the Blue Dolphin Inn, located at 404 Alamanda in the Historic Village of Anna Maria is a wonderful two bedroom, two bath upstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with fountains and nearby tiki...
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    Anna Maria, Anna Maria Island 34216
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    While Anna Maria Island is a place that you can go barefoot about twenty two hours of the day, we still don’t like to skip on luxury.  (2) Bedrooms, (1) Bath, accommodates up to (4) people: 1 King, 2 Twins. Blue Wave Villas are cozy, comfortable, and above all, classy, making this a dream vacation...
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    Holmes Beach, Anna Maria Island 34217
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    3207 Gulf Drive at Palm Isle Village in Holmes Beach, Florida is located in one of Anna Maria Island's favorite and finest condominium resorts.  It offers a fabulous holiday villa which has been designer decorated in charming Old Florida style. The one bedroom-one bath ground level villa has an...
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    Holmes Beach, Anna Maria Island 34217
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Treat yourself to the beach side vacation you’ve been dreaming of at “Palm Beach House”. This relaxing Anna Maria beach rental is in a premium location with great amenities and a beachy style. “Palm Beach House” is just two blocks from some of the best beaches you’ll find on the west coast of...
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    Anna Maria, Anna Maria Island 34216
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Located at the prestigious north end of Anna Maria, Blue Waters is brand new  to the rental program!  This home is a beautiful private resort-style villa, just minutes walk from the gorgeous white sand beaches of Anna Maria Island and a few blocks away from the individual shops, restaurants and...
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    Anna Maria, Anna Maria Island 34216
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    The large heated pool and nestled right in the sands of the Gulf of Mexico beaches. Enjoy a sunset right on your direct gulf front enclosed lanai. This unit accepts a one month stay or longer. (2) Bedroom, (2) Bath, accommodates up to (4) people 2 Kings. There are so many island activities at...
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    Holmes Beach, Anna Maria Island 34217
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    To say we live in paradise is no exaggeration and we’d like to invite you to experience it yourself with a week at Sea Palm Cottage! This vacation rental home offers room for seven guests, making it ideal for families with children. (3) Bedroom, (2) Bathroom, accommodates up to (7) people: 2...
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    Holmes Beach, Anna Maria Island 34217
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Anna Maria Island's chic upscale development offers this ground level, vacation cottage at called Sunfish Cottage! Every detail has been taken care of with our guest's relaxation in mind. It starts with three bedrooms, two and a half bathrooms all with premium, professionally laundered linens to...
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    Holmes Beach, Anna Maria Island 34217
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Anna Maria Island's chic upscale development offers this ground level, vacation cottage at called Sunfish Cottage! Every detail has been taken care of with our guest's relaxation in mind. (2) Bedroom, (2) Bath, accommodating up to (4) people: 1 King, 1 Queen. You’ll have the comfort of high rise...
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    Holmes Beach, Anna Maria Island 34217
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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 you are a sea shell throw away from the beautiful AMI beaches, and you have a pool oasis out in your own backyard. There’s room for up to...
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    Anna Maria, Anna Maria Island 34216
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Anna Maria Island still maintains an old Florida feel, with peaceful beaches and glowing sunsets, while offering a diverse choice of restaurants and activities. World class sunbathing, shelling, fishing, and swimming are right outside your door. Quite literally when you’re spending a holiday at...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    A dream come true holiday oasis perfect for large families. (6) Bedrooms, (4.5) Bath, accommodates up to (16) people: 4 King, 1 Queen, 2 Twin, 2 Sleeper Sofa. Private heated pool with spa, outdoor kitchen, free wireless, pet friendly with fee, less than two blocks to the beach. New Luxury...
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    Holmes Beach, Anna Maria Island 34217
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    Anna Maria Island Beach Side Vacation Rental Within Walking Distance to Beach1 / 25
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Brand New! Newly remodeled! Escape to this beach bungalow overlooking the bay on the beautiful desirable Anna Maria Island. This beach bungalow is nestled away in a quiet neighborhood centrally located on Anna Maria Island. The property was recently completely remodeled and everything is brand...
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    Bradenton Beach, Anna Maria Island 34217
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Blue Bayou will have you falling in love with the island life! This great canal front home is platinum rated, and includes all the amenities you expect from a relaxing Florida vacation by the beach. Not only will you be close to beaches, but near great island style attractions too! “Blue...
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    Anna Maria, Anna Maria Island 34216
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Absolutely stunning in every way! This ultimate luxury beach vacation rental home is for relaxing with family and friends at the highly coveted north end of Anna Maria Island. It's just a short stroll from Bean Point beach and an easy walk to the Rod & Reel and City piers for fishing, dining or...
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    Anna Maria, Anna Maria Island 34216
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 5 Quick View
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    Sunset Terrace Condo #201 is a newly renovated Gulf front condo with a heated pool, located at 2312 Gulf Drive in Bradenton Beach. It offers a spectacular view of the Gulf of Mexico from almost every room. This one bedroom, one and one half bath condo has a small den area. It sleeps six with a...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    The Beach House Resort #1, located at 1000 Gulf Drive in Bradenton Beach is in a gulf front complex with panoramic beach views. The white, sandy beach stretches for miles in either direction! There are numerous beach side chaise lounges to sit back and enjoy the sunsets or catch up on your reading....
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    It was Holly Golightly, as played by the immortal Audrey Hepburn, that once looked off into the distance and sighed, “Calms me down right away. The quietness and the proud look of it nothing very bad could happen to you there. If I could find a real-life place that'd make me feel like Tiffany's...”...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Elegant and comfortable, Anna Maria Island vacation rental home “Neolinda” is the luxurious vacation destination you’ve been dreaming of! This stylishly decorated 3 bedroom, 2 bathroom vacation rental home accommodates up to 6 guests with 1 king bed, 1 queen bed and a twin bunk bed. This newly...
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    Holmes Beach, Anna Maria Island 34217
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    3 Bedroom, 2.5 Bath (Sleeps 6) - “North Beach Village” 6250 Holmes Boulevard unit 72 in Holmes Beach. Relax in casual luxury and comfort at North Beach Village unit 72 Gulf Dream! This Anna Maria Island vacation rental home has everything you need for the perfect getaway with up to six friends...
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    Holmes Beach, Anna Maria Island 34217
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Turtle Cove is a little home away from home in paradise! This updated oasis is a peaceful and sunny stroll from the Gulf of Mexico and our flour soft, sugar white beaches. The unit next door is also available for rent, making it perfectly suited to multifamily traveling, reunions, wedding...
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    Holmes Beach, Anna Maria Island 34217
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedroom, 2 Bath (sleeps 4) - "Coquina Beach Club Condominiums" - 1906 Gulf Drive N, Bradenton Beach A week of light and bright luxury living is waiting for you at the Coquina Beach Club. Thisvacation condominium offers you the best of Florida vacationing – with all the decadent indulgence of...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Seagrass Flats Condo #1 is a ground level, pool side unit located at 101 25th Street North in Bradenton Beach. It is a four unit complex located near one of the widest beaches on the island and features a heated pool and barbeque area. Immediately across from the beach, you can be on the sand in...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    This cute 2 bedroom, 1 bath cottage is located at the quiet North end of Anna Maria Island just steps to beautiful white sand beaches. Only 200 yards to the beach access. Nature lovers will enjoy bird watching along the beaches at Bean Point. The Rod-N-Reel Pier is a short walk away for great...
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    Anna Maria, Anna Maria Island 34216
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    The Dolphin Dance South side, located at 803 Gulf Drive South is an impressive, two bedroom one and one half bath duplex with panoramic views of the Gulf of Mexico. Enjoy the sunsets from the large palladium windows overlooking the beach. This spacious, town home unit will sleep six with two...
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    Bradenton Beach, Anna Maria Island 34217
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    The perfect condominium with direct views of the pristine Gulf of Mexico, you’ll want to vacation at “La Casa LaMar” year after year. This ground level 3 bedroom 2 bathroom condominium comfortably sleeps 5 guests with 1 king bed, 2 twin beds and 1 sleeper sofa. Fall into a sense of peace at...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    The Azure Seas is a glorious three bedroom, two bath Gulf front home located at 779 North Shore Drive in the much desired and tranquil northern end of Anna Maria Island. Tropical paradise found!! This is the perfect place to forget your troubles and soak in the unbelievable views of the Gulf of...
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    Anna Maria, Anna Maria Island 34216
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    At the entrance to Anna Maria Island, on Perico Island overlooking Anna Maria Sound is the gorgeous 220-acre island oasis and Florida’s newest private waterfront resort. Within this gated community is our fully furnished southern coastal coach home, which features 3 bedrooms, 3 bathrooms and a...
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    Bradenton Beach, Anna Maria Island 34209
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the Four Beach Lovers (Formerly Dawg Daze). Located at 2908 Avenue E in Holmes Beach, this gulf front tropical paradise features four well-appointed and comfortable one bedroom units. Each of the four units is fully equipped and tastefully furnished. All four units feature a private...
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    Holmes Beach, Anna Maria Island 34218
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    \Welcome to Groovy Guava! This 2 bed/2 bath villa features a private, heated pool in a tropically landscaped setting. The gorgeous white sand beaches and free island trolley are just a 2 minute walk away. Load up the provided beach chairs and beach towels to enjoy a sun-soaked Anna Maria day, and...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Coquina Beach Club #101 is a beautiful two bedroom, two bath Gulf front condo with a heated pool. This spacious unit has an unobstructed view of the emerald water of the Gulf and you can walk the beach is for miles in either direction. The complex has a large heated pool and undercover parking....
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    8 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Balcony
    • Hot Tub
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy these new elevated vacation rental homes with two private lagoon style pools and lush tropical plants about two blocks to the beach in Holmes Beach. Fashionably yet comfortably decorated living rooms offers big comfy furniture centered around a new 50" flat screen TV with DVD/BluRay player...
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    Holmes Beach, Anna Maria Island 34217
    Rental Home - 8 Bedrooms, 6 Bathrooms, Sleeps 16
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Seagrass Flats Condo #4 is an upper level, gulf side unit located at 101 25th Street North in Bradenton Beach. It is a four unit complex located near one of the widest beaches on the island and features a heated pool and barbeque area. Immediately across from the beach, you can be on the sand in...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Brand New! Newly remodeled! Escape to this beach bungalow overlooking the bay on the beautiful desirable Anna Maria Island. This beach bungalow is nestled away in a quiet neighborhood centrally located on Anna Maria Island. The property was recently completely remodeled and everything is brand...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One of the best vacation spots on Anna Maria Island, “La Casa Marie” is an amazing  gulf front 3 bedroom 2.5 bathroom Holmes Beach vacation rental condominium rooming up to 6 guests with 1 king bed and 2 queen beds. Stylish and comfortable “La Casa Maria” will feel like your home away from home....
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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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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Welcome to Blue Lagoon!  This complex has one of the best community pools on the island!  Large, tropical pool with a 10' waterfall right outside your back door. The lovely upgraded kitchen offer granite countertops, stainless appliances and ample counter space for prepare meals or just hanging...
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    Holmes Beach, Anna Maria Island 34217
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Limefish, spectacular beachfront location!1 / 22
    (30)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    • Private Outdoor Pool (Heated)
    • Ocean Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Limefish, from Pineapplefish is one of the most stunning beachfront holiday rentals on Anna Maria Island, with direct access to a beautiful, almost private beach. With spectacular views across the Gulf, Limefish has a wonderful and spacious decked area across the whole of the property, where you...
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    Location Information
    Anna Maria Island, Florida 34217
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    2 Bedroom, 2 Bath (sleeps 4) - "Anna Maria Island Club" - 2600 Gulf Drive N. Unit #18, Bradenton Beach Welcome to Anna Maria Island Club! This complex offers some of the finest vacation condos in the area, and the view from Unit 18 is especially breathtaking. The Gulf of Mexico stretches out...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Smoking allowed
    About this property
    Palm Cay Condominium #1 is located at 3000 Gulf Drive in Holmes Beach, on the west side of the street for easy beach access. The complex offers a heated pool and an on site coin operated laundry room for your convenience. It’s a short stroll to shopping and restaurants or trolley stops, and the...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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