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Anna Maria Island Villas

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    Travellers to Anna Maria Island are booking July dates now. Secure your holiday rental today, and have the perfect trip.
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Anna Maria Island Stunning Waterfront home1 / 42
    (8)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    The right company can be a retreat all in themselves. So when you’re looking for an escape in Anna Maria Island with someone special, consider a week spent at PIV3211 in Holmes Beach. There is room for only two people at this one bedroom, one and half bathroom vacation cottage with a king sized...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Anna Cabana Bungalow #1 located at 3711 4th Avenue in Holmes Beach is in a ground level five unit complex that’s fun and affordable. It adjoins three other of the Cabana Bungalow units and is next door to the Cabana Beach House. With the numerous room configurations this is a perfect complex for...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Spend your Anna Maria Island vacation in five star luxury when you visit “Fernweh”. This new Holmes Beach vacation rental offers both a stylish and relaxing destination for up to eight guests. If you experience wanderlust “Fernweh” is truly the place for you with a fabulous location,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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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...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Palm Gables Condominium located at 110 36th Street in Holmes Beach is one of the most sought after Holmes Beach rental complexes. It’s in a popular, quiet area of Holmes Beach yet it’s close to shopping and restaurants. Palm Gables is a small 7 unit complex and features secured undercover parking...
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    Holmes Beach, Anna Maria Island 34218
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Beachview Condo #6 at 3704 6th Avenue in Holmes Beach, is a very comfortably furnished and recently updated unit in a smaller complex, just a few short steps to the beach and located out of the way on a dead end street. Beachview offers a heated pool, and every amenity to make your stay here a...
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    Holmes Beach, Anna Maria Island 34218
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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      Breath-taking panoramic views of the sparkling Gulf of Mexico and sugar sand beaches.  (2) Bedrooms, (2.5) Bathroom, accommodates up to (4) people: 1 King, 2 Twins. Community pool, free wireless, sorry no pets, gulf front location. Hidden Cove is a slightly ironic name for these Holmes...
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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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    This multi-level, single family vacation home offers casual island luxury across an open floor plan with volume ceilings, a large wooden terrace, and tropical yard with sparkling pool. Everything you could want in a vacation home and more sitting within 500 yards of the flour soft, sugar sand...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Grant's View ~ RA435391 / 15
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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 Dolphins swiming by! This bayfront home is furnished with beach style furniture which offers a rich and comfortable atmosphere and is fully...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Recently renovated, 2 bed 2 bath Villa perfect for families, couples or a small group of friends. Located in a quiet neighborhood with an easy 3-minute walk to the gorgeous white sand beaches of the Gulf of Mexico. You are less than a mile from historic Pine Avenue shops, restaurants, and the Anna...
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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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    • Shared Outdoor Pool (Unheated)
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    Runaway Bay 230 - Condo 2 Bedroom/ 2 Bath , maximum occupancy of 4 people. Runaway Bay ----Large complex ---right across the street from the beach. Easy beach access. Largest heated community pool on the Island, tennis, fishing dock, shuffle board and clubhouse. Upstairs unit with views of...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    You will enjoy this gulf front condominium on Florida’s Anna Maria Island. This is a smoke free two-bedroom unit right on the beach with only a few feet of sand separating you from the inviting waters of the Gulf of Mexico. Seaside Beach House is a ten unit condominium located at 102 68th Street...
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    Holmes Beach, Anna Maria Island 34218
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Coquina Moorings, located at 1407 Gulf Drive South in Bradenton Beach offers the best of all worlds. This bay front complex features a beautiful heated pool directly on the bay and a boat dock for fishing enthusiasts or bring your boat, this property has a boat slip that comes with it....
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    The Hideaway, located at 5002 5th Avenue in Holmes Beach is a gulf front home which will take you back in time when living was easy. This wonderful home was built in the 1940’s and still has the same charm and ambience of days gone by. Magnolia wood walls and ceilings throughout the home give the...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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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...
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    Holmes Beach, Anna Maria Island 34218
    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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    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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    Jukes Beach House is a charming, gulf front home located at 102 34th Street in Holmes Beach. This ground level home is conveniently located close to shopping and restaurants and on a pristine, wide expanse of beach. What could be better? This is a new and affordably priced gulf front home that...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Beautiful luxury beach front condominium for rent for the first time. There's only 2 condo's on the entire property. This condo is 3500 square feet including gourmet kitchen, dining room, living room with fireplace and built in flat screen TV. screened in lanai overlooking the Gulf of Mexico, den...
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    Anna Maria, Anna Maria Island 34210
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Anna Maria Island is not a place where you go to the beach. When you are on Anna Maria Island you are at the beach. Welcome to paradise. Featured here is a new gorgeous 4 bedroom 3 bathroom home providing you with uncompromising luxury beyond imagination. What you will love most about "The Beach...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    The Tequila Sunrise is an absolutely wonderful three bedroom, two bath home with a private heated pool. Located 309 B 59th Street in Holmes Beach, this lovely property is convenient to the beach and in a very convenient, Holmes Beach residential neighborhood. It features a washer and dryer,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Runaway Bay 1151 / 12
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Runaway Bay 115 - Condo 1 Bedroom/ 1 Bath , maximum occupancy of 4 people. Runaway Bay ----Large complex ---right across the street from the beach. Easy beach access. Tastefully decorated 1 bedroom, 1 bath unit with a nice pond view. Relax in the inviting pool, or play a game of tennis,...
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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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    2 Bedroom, 2 Bath (sleeps 4) - "Anna Maria Island Club" - 2600 Gulf Drive N. Unit #17, Bradenton Beach Enjoy spectacular views of the beach and sunsets from this wonderful Anna Maria Island vacation beachfront condo. (2) Bedroom, (2) Bath, accommodates up to (4) people: 1 King, 2 Twins. This...
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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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    • Balcony
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    Bradenton Beach Club 230 - Condo 2 Bedroom/ 2 Bath, maximum occupancy of 6 people. While the exterior hints of a quaint Mediterranean village, the chic interior is pure Anna Maria Island Americana. So well appointed with comfortable furniture,with fishing dock, pools, easy access to the beach,...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Chic and spacious, with designer quality furnishings and updated fixtures this vacation condominium is found in the coveted Anna Maria Island Club complex. (2) Bedroom, (2) Bath, accommodates up to (4) people: 1 King, 2 Twins. A flat screen television can be found in both along with a wall...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    The quintessential Florida beach side condo, you’ll love your Anna Maria Island vacation when you stay at West Winds 6828. This fun and tropical inspired coastal getaway accommodates up to four guests with two bedrooms and two full bathrooms. Nestled in the West Winds community on the Gulf of...
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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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    3 Bedroom, 2 Bath (sleeps 8) - "Coastal Sands" - 213 70th Street, Holmes Beach Welcome to Coastal Sands! It time to slow down and drag your feet in the sugar sand beaches on the Gulf of Mexico which is just a short stoll away. This is especially true of a Florida vacation and a week at Coastal...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    About this property
    The Anna Maria Escape located at 725 North Shore Drive in Anna Maria city is just that - a peaceful, relaxed place to get away from it all. You can stroll on the beach for miles in either direction! It’s a perfect Anna Maria Island vacation home! This spacious and charming two bedroom, two...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    FAMILY/CHILD FRIEDLY CONDOMINIUM. The Anna Maria Island Beach Palms is located with-in walking distance of Anna Maria Island's best waterfront restaurants, beach shops, gift shops, shell shops, boutiques and the quaint shopping village on historic Bridge St. that leads right out onto the pier,...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Welcome to the "Old Florida" charm of this well cared for ground level cottage located at 215 Fir Ave and just a few homes from the best beaches in Florida. This charming two bed two bath home sits on a quiet street yet just a trolley car ride away from exploring the island. (2) Bedrooms, (2)...
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    Anna Maria, Anna Maria Island 34216
    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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    Coquina Moorings, located at 1407 Gulf Drive South in Bradenton Beach offers the best of all worlds. This bay front complex features a beautiful heated pool directly on the bay and a boat dock for fishing enthusiasts. Immediately across the street is the white, sandy beach and the Gulf of Mexico....
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Find the perfect Anna Maria Island vacation spot at “Sugaree”! This newly renovated duplex is comfortable, stylish and close to the beach too! When you visit “Sugaree” you’ll find everything you’ll need for up to six guests. Inside this Holmes Beach rental you’ll find a spacious main living...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Coconuts Beach Front 108 Ground floor1 / 19
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    One bedroom one bath condo located on the beach. The Coconuts Beach Resort is a beach front property in Holmes Beach on Anna Maria Island. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 4. There are two double...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Sea Pirate Condo #3, located at 3301 Gulf Drive in the heart of Holmes Beach is just a stone's throw from the tropic teal waters of the Gulf of Mexico. Situated in a much desired area, close to shopping and restaurants, this smaller complex features a large, screened and heated pool, on site coin...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    9 Bedrooms, 6 Bathrooms, Sleeps 26 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    The Blue Dolphin Inn, located at 780 Jacaranda and 404 Alamanda in the tranquil City of Anna Maria features four units surrounding a tropical heated pool with tiki huts, grills, rooftop observation decks and loads of charm. Each unit has its own private patio and charcoal grill for an evening of...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 9 Bedrooms, 6 Bathrooms, Sleeps 26
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    Fantastic private "Coastal Cottage" vacation home just a few houses to the white sandy beaches of Anna Maria Island and the Gulf of Mexico. Enjoy the large heated pool with large tiki umbrella in pool bar area all in a tropical paradise setting! Enjoy the feel of this cottage for your next...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Smoking allowed
    About this property
    Welcome to the SS Salamander, South unit at 121 50th Street in Holmes Beach. This recently updated two bedroom and one 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 easily...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Anna Maria Beach Place #6, located at 201 35th Street in Holmes Beach is a charming beachside complex featuring six units surrounding a heated pool and tropical gardens. Immediately across a rarely traveled, dead end road are the white sandy beaches and the emerald green water of the Gulf of...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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,...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Smoking allowed
    About this property
    The Bollinger Duplex, side A is a very comfortably furnished and spacious duplex apartment located at 6909 Gulf Drive in the preferred, quiet area of northern Holmes Beach. This property is located about one-half block to beautiful Gulf of Mexico where you can walk for miles in either direction...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Castnetter Beach Resort #5 is a delightful Anna Maria Island rental located directly across the street from the seven acre Manatee Public Beach and the Gulf of Mexico. This beautiful and totally renovated two bedroom two unit sleeps six with a queen size bed in the master suite, two twin size...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    7 Bedrooms, 6 Bathrooms, Sleeps 24 Quick View
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    About this property
    The Islands West Resort, located at 3605 Gulf Drive in Holmes Beach, is a ground level resort with a large heated pool. Enjoy the relaxing charm of island living where you’ll feel that you've gone back to a simpler time. The resort consists of four, one bedroom, one bath units and one, two...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 7 Bedrooms, 6 Bathrooms, Sleeps 24
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    6 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
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    Smoking allowed
    About this property
     "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...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 16
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Smoking allowed
    About this property
    Just 150 steps to a beautiful white sandy beach located in the preferred and more private northern end of Anna Maria Island, The Harrison Home at 6901 Gulf Drive features many new renovations and updates. This spacious four bedroom and four bath home has one of the largest private pools on the...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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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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    Location Information
    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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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunset Terrace Condo #202 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 two bedroom, two bath condo sleeps six with a king size bed, two twin beds and an...
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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, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    The Anna Maria Island Beach Palms 7A is located with-in walking distance of Anna Maria Island's best waterfront restaurants, beach shops, gift shops, shell shops, boutiques and the quaint shopping village on historic Bridge St. that leads right out onto the pier, famous for strolling, fishing and...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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