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Anna Maria Island Cottages

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    1 / 13
    Holmes Beach
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Holmes Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 17
    5 of 5 bubbles (24) Excellent
    Bradenton Beach
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 16
    5 of 5 bubbles (2) Excellent
    Anna Maria
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Sea Waves cottage is located at north end of anna maria island. Brand new renovation, 3 bedroom with 2 bath room, with private dock, sailboat direct to bimini bay, unobstructed , natural view of bimini bay. Less than three minute walk to beach, walking distance to pine ave and the city pier and... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 15 March 2017
    We were please to find this very clean unit on the ground floor of a two story house with private entrance, private deck, and parking. It is a 10-15 minute walk to the Anna Maria...
    5 of 5 bubbles Reviewed 20 November 2016
    Absolutely perfect exactly as described . Owner Jenny very quick to respond . Secluded beautiful view of the bay !! Very easy to get around the island, perfect location...
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    1 / 22
    5 of 5 bubbles (3) Excellent
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Thank you for considering my home which has been recently updated to provide the warmth and feel of a true beach cottage. Wooden ceiling planks have been added along with pine beach chic cabinets and decor. I put many hours into the design of the home to provide a feeling of tropical relaxation.... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island 34217
    5 of 5 bubbles Reviewed 1 week ago
    Booked this place for my brothers wedding. It was very clean and only 2 blocks from beach. Would stay here again.
    5 of 5 bubbles Reviewed 3 weeks ago
    Great time in the Tree House on Anna Marie Island. Teenage girls had a blasts, while Moms relaxed. Very sort walk to beach, would not hesitate to book again.
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    1 / 22
    5 of 5 bubbles (2) Excellent
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    ANNA MARIA ISLAND #3 TOP 10 ISLAND'S IN U.S.A. Palm Isle 3203,our 2 bedroom island decorated condo is across the street from the beaches of Anna Maria Island. Steps from the heated pool and fully landscaped setting, along with all the amenities of home, your family will enjoy our beach get... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    5 of 5 bubbles Reviewed 17 January 2017
    The photos are accurate. But, in person the home is stunning. When my husband and I walked in, the first thing I said was "they must have did a background check on us"! My...
    5 of 5 bubbles Reviewed 1 December 2014
    LOVED, LOVED, LOVED this property! It's perfectly located right in the heart of Anna Marie island - easy in and out parking RIGHT in front of the villa. The villa was roomy for us...
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    1 / 23
    Bradenton Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    This charming 2 bedroom in Bradenton Beach is just steps from the spectacular beaches of Anna Maria Island and only 2 blocks from Historic Bridge Street and all the charm of our locally owned shops and restaurants. This is one of 3 units that share a beautiful pool with a small waterfall in a very... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island 34217
    1 / 31
    5 of 5 bubbles (2) Excellent
    Holmes Beach
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    This newly remodeled Florida gem backs onto 17 acres of mangrove forest and is ideally located only 3 blocks from the beach. Reasonably priced, this quaint 3 bedroom, 1 bath cottage has a spacious backyard equipped with a pool, hammock, patio furniture, grill, brick fireplace, and picket fencing,... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    5 of 5 bubbles Reviewed 6 August 2016
    April was helpful and prompt. She made the whole process from booking to check out easy! The house was cozy and just what we were looking for. I would definitely book again
    5 of 5 bubbles Reviewed 27 July 2015
    I will be going back! From reservations to communication, from check in to location and the property itself, this place is magnificent!
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    1 / 21
    4 of 5 bubbles (5) Very good
    Bradenton Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    We all know Location! Location! Location! Just yards from the beach, Palm Cottage is a beautiful cottage located in Bradenton Beach and is just steps from the Gulf. This 1 bedroom condo offers a full size, fully equipped kitchen with refrigerator, dishwasher, microwave, oven, ample cookware and... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island 34217
    3 of 5 bubbles Reviewed 13 April 2016
    The unit itself was very clean and decorated nicely. However, the beach across the street was under construction and closed. The view was of construction equipment, cranes, and...
    3 of 5 bubbles Reviewed 24 April 2015
    Enjoyed the island, it was our first time to Anna Maria and we definitely enjoyed ourselves. I wasn't impressed with the cottage. Upon arrival there was an empty lotion in the...
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    Bradenton Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    This charming 2 bedroom 1 bathroom is only the 2nd house from the beach and only 2 blocks from Historic Bridge Street. Enjoy all that Bradenton Beach has to offer from our world class beaches, to unique local shops and restaurants. This home is perfect for the couple or small family looking to... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island 34217
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    Anna Maria
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    Sea Breeze cottage is located at north end of Anna Maria island. Brand new renovation, 2 bedrooms with 2 bath rooms, with private dock, sailboat direct to Bimini bay, unobstructed , natural view of Bimini bay. Less than three minute walk to beach, walking distance to pine ave and the city pier and... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 15
    Anna Maria
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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... View all property information
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    Anna Maria, Anna Maria Island 34216
    1 / 22
    Bradenton Beach
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Good Times Cottage located one block from the beach at 305 Highland Avenue in Bradenton Beach is a newly renovated Coastal Cottage. This quiet cottage has two bedrooms and one bathroom and is decorated in a light, bright and very cheery decor. There is a great covered patio with an eating area... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island 34217
    1 / 30
    5 of 5 bubbles (2) Excellent
    Anna Maria
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    The Shady Mango was originally built in 1925. According to local history<BR>the heart pine used in constructing the original house came by steam boat<BR>to the City Pier and was hauled by horse-drawn lorry up Pine Avenue to the<BR>home's present site.<BR><BR>In 2004 the home was given a major... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 21 September 2013
    My husband, 2 kids & I stayed at the Shady Mango & LOVED it! It's the perfect place for a vacation for a small family. It's in a great location with walking access to the beach...
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    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    20771st Beach Villa -Duplex 2 Bedroom/ 2 Bath , maximum occupancy of 4 people. The perfect spot for the budget-conscious, beach-loving vacationer! This comfortable and clean 2 bedroom/2 bath elevated duplex is only 200 yards from the fabulous white sand beach and crystal-clear waters of the Gulf... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Find the paradise vacation you’ve been looking for at 202 66th street on Anna Maria Island. Enjoy accommodations for up to 6 guests just a block from some of the best beaches of the west coast of Florida! This remodeled 2 bedroom Anna Maria Island beach rental offers one king bed, one queen bed... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    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... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    The right company can be a retreat all in themselves. When you’re looking for an escape in Anna Maria Island with someone special, consider a week spent at PIV3215 in Holmes Beach.  (1) Bedroom, (1.5) Bathroom, accommodates up to (4) people: 1 King, 1 Sleeper sofa. You’ll have plenty of... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 23
    5 of 5 bubbles (1) Excellent
    Bradenton Beach
    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    This adorable vacation rental in Bradenton Beach is actually three 2 bedroom condos combined into one vacation rental package, for a total of 6 bedrooms and 3 bathrooms, and one nice swimming pool. Enjoy the sandy gulf beaches 1/2 block away. Located on Anna Maria Island, this rental package has... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island 34217
    5 of 5 bubbles Reviewed 11 August 2015
    Such a wonderful house. Perfect size for our family of 4. We had two children aged 9 + 6 and they were reluctant to leave the house to even visit the parks in Orlando because of...
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    1 / 13
    Anna Maria
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    Staying at Mangrove Cottage, known to some as simply “Mangrove Cottage”, is less about vacationing and more about seeing what it means to live the island life. This two bedroom, two bath vacation cottage will feel like home from the first time you wake up in Anna Maria Island’s sunshine and salt... View all property information
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    Anna Maria, Anna Maria Island 34216
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    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    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... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Welcome to the perfect Anna Maria Island beach rental for up to six guests at 200 66th Street! This remodeled duplex is just a block from GULF BEACHES and has a laid back feel. Everything you’ll need for a great vacation is waiting at this Anna Maria Island Holmes Beach rental. Beach trips were... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Anna Maria
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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... View all property information
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    Anna Maria, Anna Maria Island 34216
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    Holmes Beach
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    About this property
    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... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
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    About this property
    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,... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    2 of 5 bubbles (1) Poor
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    Lovely 2 bedroom, 1.5 bath Bay front home with boat/fishing dock. Beautiful views of the Bay. Located on a quiet street just one block to the beach. Located on Ana Maria Island. View all property information
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    Bradenton Beach, Anna Maria Island 34217
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    Holmes Beach
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    About this property
    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... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    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... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
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    • x
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    About this property
    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. With so many indulgent,... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
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    About this property
    2 Bedroom, 1 Bath (sleeps 4-6) - "Playa Casanas North" - 3222 Gulf Drive unit B in Holmes Beach. Welcome to the direct gulf front vacation you’ve been waiting for at “Playa Casanas North”! This Anna Maria Island vacation rental home accommodates up to 6 guests with a spectacular cozy coastal... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
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    About this property
    perfect for vacations with kids thanks to a charming set of bunk beds in the guest bedroom.  (2) Bedroom, (1) Bathroom, accommodates up to (6) people: 1 Queen, Set of short bunk beds, 1 Sleeper Sofa. Being part of our Premium Linens Programs means PIV3204 is stocked with hotel quality towels... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Bradenton Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Palm Cottage is a beautiful newly remodeled vacation rental located in Bradenton Beach, just a few steps from the sandy beaches. This 1 bedroom rental offers a  full size, fully equipped kitchen with refrigerator, dishwasher, microwave, oven, ample cookware and small appliances. You'll enjoy the... View all property information
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    Bradenton Beach, Anna Maria Island 34217
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    Holmes Beach
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    About this property
    All of the Palm Isle Villages are a good choice for family vacations.  But PIV 3206 is particularly perfect for vacations with kids thanks to a charming set of bunk beds in the guest bedroom.  (2) Bedroom, (1) Bathroom, accommodates up to (4) people: 1 Queen, Set of short bunk beds, 1 Sleeper... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
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    When a starfish needs to get away from something and can’t, it will sometimes need to detach an arm. After a week of staying in the Starfish Beach Cottages, you’ll find yourself facing a similar problem – how are you ever going to leave? The answer is, of course, by rebooking it for your next... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
    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... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Bradenton Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    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 with a refreshing swimming pool. This rental is perfect for a small family or group to enjoy. Or, a larger family and group may rent two... View all property information
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    Bradenton Beach, Anna Maria Island 34217
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    Holmes Beach
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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... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Bradenton Beach
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    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 Bradenton Beach comes with a refreshing swimming pool. Located on Anna Maria Island, this rental is perfect for a small family or group to... View all property information
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    Bradenton Beach, Anna Maria Island 34217
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    Anna Maria
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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 beach cottage rental is so close to the Gulf of Mexico you can smell the salt air! Enjoy sugar sand beaches and crisp blue water only steps... View all property information
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    Anna Maria, Anna Maria Island 34216
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    Anna Maria
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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, you’ll find a vacation rental home appropriate to the name - "Pretty Palms" on Periwinkle Plaza. This three bedroom, two bathroom cottage is... View all property information
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    Anna Maria, Anna Maria Island 34216
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    Anna Maria
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    Steps to the beach - adorable "Old Florida" beach cottage located in the heart of the city of Anna Maria. The two bedroom and two bath beach cottage rental so close to the beach you can smell the salt air. (2) Bedrooms, (2) Bath, accommodates up to (6) people: 1 King, 2 Twins, 1 Sleeper Sofa.... View all property information
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    Anna Maria, Anna Maria Island 34216
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    Holmes Beach
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    Plum Cottage 324 is professionally decorated with a laidback island flavor, and offers everything you'll desire for a truly memorable vacation! This single story, candy colored rental is directly in the heart of Anna Maria Island. Get on beat with plenty of island flavor as you’ll be close to... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Bradenton Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    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 Bradenton Beach comes with a refreshing swimming pool. Located on Anna Maria Island, this rental is the perfect accommodation for a small... View all property information
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    Bradenton Beach, Anna Maria Island 34217
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    Holmes Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Welcome to Palm Isle 3210, a one bedroom and one bathroom villa in the heart of quiet, friendly Holmes Beach on Anna Maria Island. Honeymoons, couples escapes, and smaller family vacations are just waiting to happen.  (1) Bedroom, (1) Bathroom, accommodates up to (4) people: 1 King, 1 Sleeper... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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      Create lasting memories at this island oasis just steps from eight continuous miles of uncrowded sugar-sand beach. Relax, unwind, and immerse yourself in the tropical ambience of your own private sun-dappled courtyards, but know that world-famous Anna Maria Island, and all it has to offer, is... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
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    When a starfish needs to get away, it is more than prepared to detach an arm in order to do that. Don’t let yourself get that stressed! Stay for a week in Starfish Beach Cottages and feel all your cares and worries just fall away. From the moment you arrive, you’ll feel like this vacation cottage... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    Direct Gulf Front cottage in Holmes Beach! When we say that Sea la vie is right on the beach, we mean one step off the back porch!  (2) Bedroom, (1) Bathroom, accommodates up to (5) people: 1 Queen, 1 Twin, 1 Sleeper Sofa. Open the windows and fall asleep to crashing waves. Sea gulls and... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
    3 Bedrooms, 3 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! Dogs under 50lbs are welcome with a pet fee. The lovely upgraded kitchen offers granite countertops, stainless steel appliances and... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
    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... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Anna Maria
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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      Willow Cottage is a lovely ground level bungalow in Anna Maria just waiting to give you that tropical vacation you dream of and deserve! This private rental home is stylishly decorated with touches of both new and old Florida. From the whimsical coastal print comforters to cool tile floors... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216