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Beach Rentals and Cottages in Anna Maria, FL

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    Travelers to Anna Maria are booking March dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 39
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 23
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    1 / 22
    5 of 5 stars (3) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    1 / 24
    4 of 5 stars (1) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Located on the north end of Anna Maria Island in the city of Anna Maria on historic Pine Avenue, this two-bedroom, one-bathroom second-floor vacation rental condo has been completely updated and is picture perfect. So much so, once you walk through the front door you'll feel as though you just... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    4 of 5 stars Reviewed October 26, 2015
    We love Anna Maria! This 2 bedroom condo was ideally located right on the canal, which is right off Tampa Bay. We were able to drop our paddle boards or kayaks right off the...
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    1 / 20
    5 of 5 stars (1) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
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    About this property
    116 Maples is located on one of the prettiest streets in the village of Anna Maria, this gorgeous 4 bedroom, 2 and a half bath home is just steps away from the beach. This quiet, tree-lined street evokes memories of Florida Gulf Coast islands in days gone by, with a shaded path providing access to... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed November 2, 2015
    Wonderful location, The beach is at the end of Maple Ave, a quiet road only a 2 minute walk. The house is well situated, 4 bedrooms and 2 and 1/2 baths. I can only speak of the...
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    1 / 24
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Life is Good at the Beach, located on the north end of Anna Maria Island, is a fantastic place to start your vacation. This three-bedroom, two-bath, vacation rental is just a five minute walk to the beautiful north end beaches near Bean Point and two blocks to the Rod & Reel Pier. The extra-large... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 3 weeks ago
    Life is Good at the Beach vacation rental is a beautifully, well maintained home. The picutres provided on the website accurately reflect the home and the beach house more than...
    4 of 5 stars Reviewed November 22, 2015
    Great well equipt house, everything we needed and more, close location to beach 5 mins walk, and to the free trolley bus stop 10 mins walk. The only downside of this property is...
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    1 / 35
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Looking for that place to kick back and relax your cares away? Check out ‘Triple Play Guest House.' There's a triple chance to play: (1) walk to the beach, (2) lounge in the pool or spa or patio or (3) launch a kayak, fish or just relax on one of our two docks on the canal. Nothing quite compares... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed June 24, 2015
    This house is nothing less than spectacular for a family. The house has been completely redone inside. The house looks very small from the front / driveway, but the inside is...
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    1 / 23
    5 of 5 stars (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Stunning ground level 3 bedroom/2 bath home with luxury finishes at every glance. Brand new to the market and recently renovated, this home is packed with designer finishes throughout from luxury linens in all three uniquely appointed bedrooms to furnishings that make this home feel like you are... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34217
    5 of 5 stars Reviewed 3 weeks ago
    This canal home (just houses away from the bay) is lovely and well appointed. Our landlords, Mathias and Carren, met us at the home at check-in and showed us everything which was...
    5 of 5 stars Reviewed August 25, 2015
    These house is confortable,clean, cozy!! Confortable rooms!.You can see the fresh water from the window ! Walk 10 steps to a nice private deck, with beautiful birds, manatees...
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    1 / 39
    5 of 5 stars (3) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 11 | Quick View
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    • Internet Access
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    About this property
    When you 'have anna maria' on your mind, you'll want 'hav'anna hideaway' for your vacation home. This newly constructed 4 bedroom, 4 bath home is located just one short block to the beautiful and sparkling gulf beach. The main floor of the home consists of an open concept living room, kitchen with... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed August 27, 2015
    This property was everything we had hoped for and more! Centrally located in one of the best parts of Anna Maria Island, and even though it was close to one of the main streets it...
    5 of 5 stars Reviewed August 8, 2013
    The house is beautiful, very well-equipped (although we missed the grill), very comfortable, and a short walk to a wonderful beach. It was just right for the grandchildren and...
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    About this property
    This gorgeous three story home in the city of Anna Maria, is an easy walk from Pine Avenue and the City Pier, with direct water views, front and rear, from all living spaces. With 5 bedrooms, 5 baths,4 balconies,3 living areas, an elevator, and a heated salt water pool, you have everything you... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
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    1 / 22
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Washer
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    About this property
    This lovely two bedroom family- and pet-friendly Anna Maria Island vacation rental is just a few houses from the island's white sand beach and azure blue waters of the Gulf of Mexico. Located on the quiet north end of the island in the city of Anna Maria, at 950 square feet, this classic elevated... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed October 17, 2015
    We saw this rental a year or so ago when we were staying on Anna Maria Island. We looked it up on line and was happy with what we saw. The home sleeps a family of four. It was...
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    1 / 33
    4 of 5 stars (4) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Grill
    • Satellite TV
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    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • x
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    • Smoking allowed
    • Elder access
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    About this property
    Beautiful 2B/1B cottage on the quiet North end, only 5 houses to the beach, and no streets to cross. Beautiful new Heated Pool. Twins can be converted to King in all bedrooms. NO dishwasher, no garbage disposal.Rear trash pick up! Charcoal Grill, not gas. Both units also include private... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    4 of 5 stars Reviewed 4 weeks ago
    This was our first time on the island. This house is a short 5 minute walk from a fabulous beach, and you share a pool with the other side of the duplex. The neighbourhood...
    5 of 5 stars Reviewed June 8, 2015
    The cottage was just as the picture depicts. It was close to the beach and we only had to worry about 1 other rental on the property. A lot of privacy and all the amenities...
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    1 / 24
    2.5 of 5 stars (2) Poor
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Porch
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    • Pet-friendly
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    • Child-friendly
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    • Elder access
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    About this property
    Enjoy your vacation in this charming, one-bedroom, one-bath original house just six houses away from the white sand beaches of Anna Maria Island and sparkling waters of the Gulf of Mexico. Flamingo House is perfect for anyone who needs a quick weekend getaway or an extended stay! Located in Anna... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    3 of 5 stars Reviewed June 15, 2015
    Great location, and very quiet, even though it is on Gulf Drive! Very cool vintage vibe - felt like we were on a 1950/60 vacation. I was surprised that it was an apartment and...
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    1 / 26
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
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    • DVD Player
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    • Air Conditioning
    • Waterfront
    • Hot Tub
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    Newly remodeled 2 bedroom/2 bath home. Brand new pool, hot tub, and landscape with a serene canalfront setting. Located on a quiet dead-end street, close to the trolley, the beach, and walking distance to Anna Maria shops and restaurants. Bring your boat and take part in some of the best fishing on... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed January 13, 2014
    We have just come back from a 2 week stay at Lazy Lagoon. House beautiful, all on one level and flooded with light. Pool and hot tab a fantastic feature. House fully equipped and...
    5 of 5 stars Reviewed November 18, 2013
    This was our (Mom, Dad, Teen Son) 2nd time renting with anna Maria Island accommodations and our 2nd just loved it rental. Upon finding out the property we had rented the year...
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    1 / 24
    2 Bedrooms, 1 Bathroom, Sleeps 3 | Quick View
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    • Satellite TV
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    • Outdoor Dining Area
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
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    About this property
    Spend your vacation in this adorable, cozy and quiet Enchanted Cottage, just steps from the white sand beaches and clear blue waters of Tampa Bay and a short walk to the Gulf of Mexico. This lovely family- and pet-friendly cottage is located on the north end of Anna Maria Island and is surrounded... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 30
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • Pet-friendly
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    About this property
    Canal Place is a restored three bedroom, three bath Old Florida island home with a pool and hot tub; neutral and relaxing decor with a spacious living room and just a short stroll to the white sand beaches if Anna Maria. Direct waterfront with beautiful canal views. Sleeps upto 8 people. Amenities... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34217
    5 of 5 stars Reviewed October 30, 2013
    We stayed here for a week in October with seven of us and had a great time! The house was incredibly well equipped-the kitchen was stocked with lots of plates, bowls, glasses...
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    1 / 36
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
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    About this property
    Step into an ultra private, secluded, tropical paradise with a lush canal front setting in quiet cul-de-sac located on the north end of Anna Maria Island. There is a beautiful heated pool just steps outside your door. The back yard has multiple areas to relax away the day and enjoy the amazing view... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34205
    5 of 5 stars Reviewed September 30, 2015
    I chose Island Oasis as it ticked every box. This is a beautiful island and the beach is very easy to access, as such I wanted a property with a pool, suitable for two couples...
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Internet Access
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    • Pet-friendly
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    • Child-friendly
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    About this property
    This quaint, old-Florida style rental is nestled in the north shore area of Anna Maria Island. Shabby chic style, located 2 blocks from the beach and 2 blocks from the bay! Only one block from Pine Ave., with its old-time feel with shops and salons. Steps from fine dining, the historic city pier,... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 24
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    About this property
    Anna Cabana A is the perfect getaway! Located on the north end of Anna Maria Island and just a short stroll to the beach, this cute bungalow beckons you to stay and relax. This adorable vacation rental has been completely refurbished inside and out! A queen bedroom and a full bunk with twin over,... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    1 / 30
    3 of 5 stars (1) Average
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
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    • Grill
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    • DVD Player
    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • x
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    • Smoking allowed
    • Elder access
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    About this property
    Beautiful 2B/1B cottage on the quiet North end, only 5 houses to the beach, and no streets to cross. Beautiful new Heated Pool. Twins can be converted to King in all bedrooms. NO dishwasher, no garbage disposal.Rear trash pick up! Charcoal Grill, not gas. Both units also include private... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    3 of 5 stars Reviewed September 26, 2015
    We stayed here in May, and the unit was tastefully decorated, and had a cozy feel to it. However, my husband and I were getting bitten at night, and we called management to have...
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    1 / 20
    5 of 5 stars (3) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Wheelchair access
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    • Elder access
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    About this property
    Great 1 Bedroom/1 Bath remodeled cottage on the quiet North End with outdoor patio, ceramic tile throughout, and granite countertops. The allure of the Gulf of Mexico Beach just 250 steps away. A back yard dock on Lake LaVista Bayou with a patio table, umbrella, and sling back chairs. Launch the... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed January 20, 2014
    We were very pleased with our stay at Snails Pace. Not being familiar with the area and booking online, one is never quite sure what to expect. The location was great, just a...
    5 of 5 stars Reviewed November 14, 2013
    This cottage was exactly what my wife and I wanted for our honeymoon. It was super close to the beach and was definitely within walking distance of almost all of the restaurants...
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    1 / 28
    5 of 5 stars (2) Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    About this property
    Beautifully remodeled 3 bedroom/2.5 bath home with luxury amenities on the North End of Anna Maria, just 4 houses to Bean Point, one of the quietest beaches on the island, and 2 blocks to the famous Rod & Reel Pier! Private Backyard with Heated Pool, and an open floor plan with vaulted ceilings!... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed September 28, 2013
    This was my first trip to anna Marie Island. The area and weather is gorgeous in april. The accommodations are amazing with everything you can possible want or need provided. I...
    5 of 5 stars Reviewed September 27, 2013
    Pictures do not do this residence justice! We had a great time on the island and couldn't have asked for a better place to stay. The pool is perfect for relaxing and small kids...
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    1 / 20
    5 of 5 stars (3) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Description We are located in the heart of the beautiful city of Anna Maria FL. We are one block from the historic Pine Ave with free trolley service to the entire island. We are two blocks to the beautiful white sand beach. Three blocks in the opposite direction is the bay and the historic City... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed November 6, 2015
    We loved this rental. Rick, the owner, was insanely responsive -- emailing back within minutes the few times we emailed. A good friend and I came here for a creative retreat...
    5 of 5 stars Reviewed September 15, 2015
    This place was great! The house had everything we needed and is in the perfect location! There was plenty of room and tons to do and I'd definitely stay again.
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    1 / 24
    5 of 5 stars (1) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Waterfront
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    • Pet-friendly
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    • Child-friendly
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    • Elder access
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    About this property
    This is the vacation rental home of your dreams! This custom bay-front home on the north end of Anna Maria Island offers 3600 square feet of luxury accommodations and has all the fine touches and professional craftsmanship one would expect in a high-end custom home. When walking into this amazing... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    5 of 5 stars Reviewed 6 days ago
    A beautiful home that accommodates a large family. We couldn't find a better place to celebrate our dad's 75th birthday. Extremely clean and very comfortable furnishings!! We were...
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Ocean Views
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    • Pet-friendly
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    • Child-friendly
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    About this property
    This water front, two bedroom condominium (ground floor), sits on the end of Pine Avenue, across the street from the beach and has wonderful seaside views of the bay. It also has its own private fishing dock and boat slip! This unit has been completely remodeled and newly furnished to give you the... View all property information
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    Anna Maria, Anna Maria Island 34216
    1 / 34
    4.5 of 5 stars (9) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Upscale luxury executive four bedroom waterfront home with private pool dock and elevator. Stylishly furnished and dressed, modern build 2006 - this is our family second home - and is home from home available to you. This exclusive executive property is in the heart of lovely Anna Maria... View all property information
    Location Information
    Anna Maria, Anna Maria Island FL34216
    4 of 5 stars Reviewed 3 weeks ago
    We spent a week in this lovely home. The weather was cool, so we didn't use the pool, but there was a beautiful pool with a dock right out the back door. The home was spacious...
    5 of 5 stars Reviewed January 6, 2016
    We couldn't ask for a better place to have a family vacation. The atmosphere is relaxing, restful. The location is perfect.Although it is right on Pine Avenue, the backyard is a...
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    5 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
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    About this property
    Enjoy our Luxurious Villa diPalma, a beautiful six bedroom, four bathroom luxury island home very close to the best beach in the Northshore. The Italian influence in the design is reminiscent of properties found in Venice and Tuscany. The two master suites each have their own Jacuzzi spa tub, a... View all property information
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    Anna Maria, Anna Maria Island 1234
    1 / 40
    5 of 5 stars (4) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Beachcombers is a spacious 3 bedroom/2 bath home with all of the 'Old Florida Charm' you could ask for. Situated on Spring Avenue, just a couple of blocks to the Gulf of Mexico on Anna Maria's beautiful north end! Easy walking distance to many shops, restaurants, the Anna Maria City Pier and a... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed January 4, 2016
    Anna Maria is a laid back bohemian little island - where the pace of life (and cars) is slow. The house is in a prime location - near both beaches. Very near (5 minute walk) to...
    5 of 5 stars Reviewed December 13, 2015
    My boyfriend and I came to Anna Maria with his family this summer. The house was spacious, comfy and beautifully finished. There were 6 of us altogether and we had more than...
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    1 / 17
    4 of 5 stars (1) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Light, airy and spacious living in this beautiful home on Anna Maria! 3 large bedrooms with 2.5 baths, raised home with two floor screened in pool! Relax by the pool in the large open area. Perfect for entertaining. 707 N. Bay Blvd. ---In the City of Anna Maria--Beautiful 3 bedroom, 2 .5 bath... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    4 of 5 stars Reviewed June 12, 2011
    Rental selected on line for location andamenities provid - all lived up to expectations.This was my second stay ay a.M.island,first time with your company.Tried to book again for...
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    1 / 25
    5 of 5 stars (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Great Ground Level 3 Bedroom/2 Bath Home with a Heated Pool located in the quiet north end and just 3 houses to the beach!! King-Sized master bedroom with TV, Queen in the 2nd Bedroom with TV, and Twins in the Third with TV. Cable TV, DVD, and Flat Screen TV in Living Room. High speed Internet,... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed October 27, 2013
    This beach house was a winner--the house was decorated tastefully and put us in the beach mood the moment we walked thought the door. Everything we needed was supplied, pool was...
    5 of 5 stars Reviewed August 22, 2013
    Anna Banana house was pristinely clean, well-decorated, cozy, had plenty of room for the 4 of us, and was the most convenient place we have ever stayed on anna Maria Island. It...
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    1 / 24
    4.5 of 5 stars (9) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    BON AMI will be your 'good friend' after a vacation stay. Located on the north end of Anna Maria Island and a short distance to Bean Point, this heated pool stilt home will beckon you back year after year! Beautifully decorated, this three-bedroom, two-bath vacation rental is spacious, airy, and... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed June 23, 2015
    Villa was exactly what we were looking for infact better than what I imagined,location great all it's amenities good and very well kept and presented would recommend to others
    4 of 5 stars Reviewed November 1, 2014
    We're a family from Germany and booked Bon Ami via Homeaway/FeWo direkt. Our stay was all in all very nice: the location is nearly perfect, only a few steps to the beach. The...
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    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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. This unit will sleep six with a queen size bed, two twin beds and a sofa bed. Many new upgrades to this unit have... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Skiing: Property Is...
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    • Central Heating
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    About this property
    Location + Renovation = Perfect Vacation! Two houses to the beach, West of Gulf Avenue and located in the heart of Anna Maria sits the newly and completely remodeled and redecorated Angelfish. A few short blocks to the shops and restaurants of Pine Avenue, this L-shaped ground level home is... View all property information
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    Anna Maria, Anna Maria Island 34216
    1 / 30
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
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    About this property
    Newly Remodeled 3 Bedroom/3 Bath with Queen Master, Queen 2nd Bedroom, and Twin Bunk Bed with Twin Trundle. New Pool and landscape, with a quiet canalfront setting. Located on a quiet dead end street, close to the trolley, the beach, the city pier, and walking distance to Anna Maria shops and... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • ?
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    • x
    About this property
    This villa is quaint and adorable tucked in a quiet neighborhood just 9 houses from the Gulf of Mexico and white sandy north end Anna Maria Island beaches. Step outside your door and stroll down the street in 1 minute or less to the quaint shops and cafes along Pine Ave. Walk to everything the... View all property information
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    Anna Maria, Anna Maria Island 34216
    1 / 17
    4.5 of 5 stars (35) Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Internet Access
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    • Private Yard
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    About this property
    Berryfish is a fantastic new Caribbean style, beachfront apartment from Pineapplefish, ideal, due to its flexible accommodation, for larger groups of families and friends. Berryfish is double duplex apartment just a stroll to the beach, with 2 separate accommodations - Berryfish East and West,... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed June 10, 2015
    We stayed at Berryfish for our Wedding Weekend with some of our bridal party. It was perfect for us! The rooms were spacious and clean, the living room and kitchen were huge and...
    5 of 5 stars Reviewed April 24, 2014
    Berryfish was an amazing place to bring your family to! We rented both sides. We brought our oldest daughter and her family. We had our privacy and they had theres. The deck above...
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    1 / 24
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
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    • Elder access
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    About this property
    Start your relaxing vacation at Beach Walk, located just a block from the white sand beaches of Anna Maria Island. This lovely two bedroom, one bath, home has just been completely remodeled and fabulously decorated! Cozy and relaxing furnishings await you and your friends and family during your... View all property information
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    Anna Maria, Anna Maria Island 34216
    1 / 43
    5 of 5 stars (10) Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    WELCOME TO ALL DECKED OUT! Whether getting away for a family vacation, with a group of friends, for a wedding or any other occasion, our gorgeous 5 Bedroom home offers everything you could want for a relaxing holiday on Anna Maria Island.... with incredible views of the Bay! Sit by the tropical... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed November 3, 2015
    We have just come back from this wonderful house, Love the island and really enjoyed where this property is located. We were a 2 family group and there was plenty of room. Would...
    5 of 5 stars Reviewed October 26, 2015
    The location of the home was perfect for my family and I. We enjoyed several beaches all within the same area. The home exceeded our expectations, we will be returning.
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
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    About this property
    Beautifully renovated beach cottage in the heart of the village of Anna Maria. Walk to the beaches, shops and restaurants. Enjoy amazing sunsets at the beach or sip a glass of wine in the lush tropical gardens surrounding the cottage. 2 bedrooms with 2 full bathrooms. Quaint beach cottage in a... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Porch
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    About this property
    In a tropical setting, complete with pool and large sun deck. Just a short walk to the beach. Our visitors love biking the island and taking walking tours to the various places of interest on the island. There are four bedrooms and three baths. The master suite has a king bed and a Roman tub. The... View all property information
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    Anna Maria, Anna Maria Island 34217
    1 / 31
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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    • Ocean Views
    • Washer
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    • Pet-friendly
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    About this property
    Welcome to Yellowfish, one of the most exclusive rental homes on Anna Maria Island. Yellowfish, is a stunning and luxurious, 3 bedroom home, built across 2 beachfront plots on North Shore Drive, recognised as the most exclusive address on Anna Maria. This 3,000 square foot contemporary and elegant... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 1 week ago
    From the moment we arrived we knew we had made the right decision. Yellowfish was beautifully laid out. We arrived late a night and these was a basket of Goodies left out for us...
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    1 / 24
    4.5 of 5 stars (5) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
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    • Waterfront
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Come and enjoy your own private Island Oasis! Located on the north end of Anna Maria Island in the city of Anna Maria, one block from the bay and a few blocks from the City Pier, this charming vacation rental will allow for some serious relaxation. This home-away-from-home offers two bedrooms and... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    4 of 5 stars Reviewed July 23, 2015
    Nice rental,clean,well maintained,good location,but a few items that need to be taken care of. 1) The furnished outdoor grill was so rusted that it proved to be unusable,adding...
    5 of 5 stars Reviewed October 5, 2014
    This vacation rental is just perfect - the interior is so lovely, the kitchen well equiped,the surrounding amazing! We can totally recommend this home and would love to come back!
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Child-friendly
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    About this property
    As an artist this private three bedroom and two bath elevated vacation home has been a retreat that inspires many paintings of Anna Maria Island. Located on the secluded North End you will enjoy the tranquility of the Island and have an easy stroll to the Gulf of Mexico and the best white... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34217
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Beachy Keen!~ Here delightful and fun Caribbean Cool décor welcomes you to the sub tropic cozy of Anna Maria Island. A charming island home within easy walking distance to the beach, offers an ideal location for those wishing to escape wild,wintry weather or sizzling city summer. Located in... View all property information
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    Anna Maria, Anna Maria Island
    1 / 25
    5 of 5 stars (5) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
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    • Pet-friendly
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    • x
    • x
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    About this property
    This adorable remodeled duplex sits quietly in the highly desirable north end of the Island in the City of Anna Maria. It is a short walk of only a little more than a block to the Gulf beach where the sand is sugary white and the water is a beautiful blue-green color. There is a King in the... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 3 weeks ago
    A great 2 bedroom duplex with a waterfall pool,on the northern part of Anna Maria Island. Walking distance to the beach (2 blocks). The rental was clean and well maintained, the...
    5 of 5 stars Reviewed September 3, 2015
    Stayed here for a week. Nice apartment, clean and useful accomodation. Any small issues were sorted really quickly by agent who was very helpful and only 2 mins away in...
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Spend your vacation just steps from our beautiful beaches and crystal-clear waters! Casa Blanca is in the heart of the village of Anna Maria, and west of Gulf Drive...there's no better place to be! Only 5 houses from the beach, you'll be steps from the sand AND just moments from shopping,... View all property information
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    Anna Maria, Anna Maria Island 34216
    1 / 23
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
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    About this property
    Start your relaxing vacation at Sea Oats, located just a block from the white sand beaches of Anna Maria Island. This lovely two-bedroom, one-bath vacation rental has just been completely remodeled and fabulously decorated! Cozy and relaxing furnishings await you and your friends and family during... View all property information
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    Anna Maria, Anna Maria Island 34216
    1 / 29
    4 of 5 stars (5) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • Child-friendly
    • x
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    • Elder access
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    About this property
    Cherryfish is the latest addition to the Pineapplefish collection of houses on Anna Maria Island. It is a spectacular 4 bedroom house, in a fantastic location, just one block from Tampa Bay Beach, the amazing Waterfront Restaurant and the island's most popular tourist destination - City Pier.... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed January 29, 2015
    Flawless! Cherryfish, a tropical hideaway I never want to leave! The landscaping is unsurpassed providing a private tropical oasis retreat. The home itself is so fresh with...
    4 of 5 stars Reviewed April 14, 2014
    This home was wonderful for our two families of four. Plenty of space for everyone and the pool was perfect. The only complaint we had was the cleanliness upon arrival, there...
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    1 / 9
    5 of 5 stars (14) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Charming, newly renovated, the Becker Beach Bungalow offers a comfortable stay less than 2 blocks from the beach. Accommodates 6 people comfortably; master bedroom with 1 queen bed and second bedroom with 2 twin beds. The living room also has a queen size sofa bed. Relax and enjoy the quiet of Anna... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed July 28, 2015
    This beach house was even better than we expected. Everything you need! The walk to the beach was just perfect about 2 minutes. We had perfect weather everyday. Bruce and...
    4 of 5 stars Reviewed May 13, 2015
    The accommodations were extremely reasonable for what was received. The property manager was more than accommodating, dropped off a cooler for me to use to transport flowers for...
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    1 / 41
    5 of 5 stars (2) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • ?
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    • x
    About this property
    It doesn't get much better than being right on the water, ½ block from the bay beach, and only 7 blocks from Pine Avenue. Sunshine Cottage couldn't be a better name, because this 3 bedroom, 2 bathroom, cottage truly lets you experience the beauty of Anna Maria Island. Enjoy dangling your feet off... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed December 1, 2015
    We enjoyed our stay at Sunshine Cottage! This home is very clean and very spacious for 6 guests. We loved the flexibility of heading to the beach or relaxing in our own...
    5 of 5 stars Reviewed November 4, 2015
    This charming cottage was perfect for a relaxing getaway. The house is well kept, cute and fully met our needs. We took full advantage of the pool each day. I like that the owners...
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