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$157

2 BR / 1 BA / Sleeps 6

7 Reviews

$157

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Pineapple Cottage: 2BR Quaint Pet-Friendly Cottage

2 BR / 1 BA / Sleeps 6 | Quick view
“ Excellent ” 7 Reviews

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Reviews

(7)

Pineapple Cottage, centrally located on historic Pine Avenue in the city of Anna Maria, is the perfect place to slow down and catch your breath! This Anna Maria Island cottage is tastefully decorated with wood floors, granite and stainless kitchen, tiled shower and comfortable furnishings. The master bedroom boasts a…
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Porch
  • Pet friendly
  • Suitable for children - over five
  • Suitable for the elderly

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Reviews

(7)

peaceful place

Left on Jul 25, 2013 for a stay in June 2013

I love aMI, I am a visitor since 2003 from Miami. I love, love this place and Pineapple Cottage was the best place for us to stay. I felt right at home with all the comodities anyone can desire. We thank you for sharing this house with us. See you soon.

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$250

3 BR / 3 BA / Sleeps 6

1 Reviews

$250

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Anna Maria Cottage

3 BR / 3 BA / Sleeps 6 | Quick view
“ Very Good ” 1 Reviews

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Reviews

(1)

Anna Maria Cottage 104 Magnolia Avenue Anna Maria Island, FL 34216 This beautiful historic beach cottage is a true embodiment of "Old Florida Charm". This wonderful home offers 3 suites, each with their own en-suite full bathroom, a wrap around porch with stunning Gulf views and much more! Just steps from the…
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    Reviews

    (1)

    Great location!

    Left on Feb 23, 2015 for a stay in February 2015

    I spent almost 3 weeks on AMI sharing this lovely cottage with my sister and some other friends and family. The location is wonderful, very close to the beautiful beach, so an easy stroll over for sunsets and long walks, and quite near the Sandbar and restaurants and shops on Gukf and Pine. The cottage is nicely decorated with vintage signs, historical photographs and local art, and the furniture…

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    $608

    9 BR / 6 BA / Sleeps 26

    5 Reviews

    $608

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    Blue Dolphin Inn - all units

    9 BR / 6 BA / Sleeps 26 | Quick view
    “ Excellent ” 5 Reviews

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    Reviews

    (5)

    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 gas grill for an evening of relaxation. Every …
    • Shared outdoor pool (unheated)
    • Internet Access
    • Grill
    • Pet friendly - ask
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (5)

    Fun and relaxing family vacation spot

    Left on Aug 03, 2012 for a stay in July 2012

    First time we have done this kind of vacation and it turned out wonderful! This was a great location for our family get together. Each unit complete with home style living to allow personal space as well as be able to host other family from ajoining units for visits. Our family from ms, SC, IL, and FL enjoyed the space and the private fence that included a pool as well as tiki bar! 2 blocks …

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    $190

    2 BR / 2 BA / Sleeps 10

    17 Reviews

    $190

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    Anna Maria Escape

    2 BR / 2 BA / Sleeps 10 | Quick view
    “ Excellent ” 17 Reviews

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    Reviews

    (17)

    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 bath Gulf front home has …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Grill
    • Pet friendly
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (17)

    peaceful tranquilty

    Left on Feb 23, 2009 for a stay in July 2007

    No need to travel to paradise when it is right here in our own backyard. The Escape provided everything we needed and had plenty of room for our family of 6. We already know we'll be coming back to the Escape.

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    $290

    5 BR / 3 BA / Sleeps 12

    6 Reviews

    $290

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    Gorgeous views,spectacular home!

    5 BR / 3 BA / Sleeps 12 | Quick view
    “ Excellent ” 6 Reviews

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    Reviews

    (6)

    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 courtyard garden, …
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly - ask

    Details

    Reviews

    (6)

    A week of Bliss!

    Left on Jan 09, 2014 for a stay in May 2013

    We were able to spend a week of absolute delight, fun and relaxation. The rooms are large (huge master bedroom). Flat screens in every room, Ipod docking stations everywhere, plenty of everything and large living areas. Yet the best were the views for the decks. The location is perfect. We will definitely return regardless of whether or not 5 bedrooms are needed!

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    $600

    3 BR / 2 BA / Sleeps 8

    1 Reviews

    $600

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    Serendipity

    3 BR / 2 BA / Sleeps 8 | Quick view
    “ Excellent ” 1 Reviews

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    Reviews

    (1)

    Our home is a Direct Beach Front 3 bedroom- 1 & 1/2 bath residence furnished with all the comforts of home. Panoramic view of the Gulf of Mexico from your soothing beach cottage style home and decor. The living level has a full size kitchen, half bath, great room and dining room in an open floor plan to capture …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Fireplace
    • Housekeeping Optional
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (1)

    The house name says it all

    Left on Jan 17, 2014 for a stay in September 2013

    3 nights here and 11 near Disney. Asked the kids what part of the holiday they preferred - "the one with the house on a beach!". For us that said it all. Buckets and spades Vs Mickey Mouse. Who would have believed the winner.
    This place is perfect. Apprehensive with the white interior and kids, but they were always on the beach. It really is a restful retreat for all types - families, couples and…

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    $223

    2 BR / 2 BA / Sleeps 6

    1 / 29

    $223

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    CHAMPAGNE SHORES

    2 BR / 2 BA / Sleeps 6 | Quick view

    Details

    This great 2 Bed/2 Bath Home with Private Heated Pool resides in Anna Maria and is only one block to the beach and has no busy streets to cross to get there. You can quickly make your way to the Gulf Sands and to all of the great shops and restaurants that Anna Maria and Holmes Beach have to offer. Furnished very …
    • Shared outdoor pool (unheated)
    • A/C or climate control
    • Parking
    • Grill
    • Suitable for children
    • Suitable for the elderly

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    $257

    3 BR / 2 BA / Sleeps 8

    1 Reviews

    $257

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    OURPLACEBYTHESEA

    3 BR / 2 BA / Sleeps 8 | Quick view
    “ Average ” 1 Reviews

    Details

    Reviews

    (1)

    Beautiful ground level 3 bedroom/2.5 bath home, with a quiet north end location only a block to the beach! There is a King in the master with a private patio, a Queen in the second, twin beds in the third, and a queen sleeper sofa in the sunroom (which has blinds for privacy), all accommodating up to 8 people. …
    • Shared outdoor pool (unheated)
    • A/C or climate control
    • Parking
    • Grill
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (1)

    Great location, pool

    Left on Jul 01, 2014 for a stay in June 2014

    We had a great time on Anna Maria with our two college-aged sons. This house is very nicely located, and the pool is wonderful. The home was spacious and comfortable for four people. Our main negative was the beds. All of them were uncomfortable with lousy, flimsy, worn-out mattresses. Also, the kitchen was in some regards well-equipped, but lacking in quality and quantity of pots/pans/…

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    $274

    4 BR / 2 BA / Sleeps 8

    6 Reviews

    $274

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    HAWAIIAN PUNCH

    4 BR / 2 BA / Sleeps 8 | Quick view
    “ Excellent ” 6 Reviews

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    Reviews

    (6)

    Beautiful, cheerful and tropucal 4 bedroom/2 bath home with beautiful new furnishings throughout! Comfortable and roomy with split floor plan (two bedrooms on each side!). Ceramic tile throughout, beautiful open kitchen area with breakfast bar and granite countertops. The living room opens up onto a large paver deck …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (6)

    Best vacation ever!

    Left on Aug 02, 2013 for a stay in May 2013

    This was our "family come together" vacation as we live in 4 different locations. We loved our rental house because it offered everything we needed - enough accommodations, pool, fenced in yard, dock access to canal, and absolutely perfect location as to proximity to shops, pier, and beach. It also helped that we had the best weather ever! It seems that every time we talk to any of our kids, …

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    $175

    2 BR / 2 BA / Sleeps 6

    6 Reviews

    $175

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    Blue Dolphin Inn - Heron Up

    2 BR / 2 BA / Sleeps 6 | Quick view
    “ Very Good ” 6 Reviews

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    Reviews

    (6)

    The Heron unit at the Blue Dolphin Inn, located at 404 Alamanda in the Historic Village of Anna Maria is a wonderful two bedroom, two bath upstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with fountains and nearby tiki table. The Blue Dolphin…
    • Shared outdoor pool (unheated)
    • Internet Access
    • Grill
    • Pet friendly - ask
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (6)

    great location

    Left on Mar 30, 2011 for a stay in March 2011

    we enjoyed our second stay at the blue dolphin. the unit has a great floorplan, huge porch and was very nicely appointed and decorated. everything was new and comfortable, the kitchen had everything needed and every appliance. washer and dryer and most furniture new, unit was freshly painted and tastefully decorated. location was superb.

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    $300

    4 BR / 3 BA / Sleeps 14

    1 Reviews

    $300

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    Ocean Walk

    4 BR / 3 BA / Sleeps 14 | Quick view
    “ Excellent ” 1 Reviews

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    Reviews

    (1)

    Ocean Walk 117 Willow Avenue Anna Maria Island, Fl 34216 Ocean Walk is a brand new private home that is now ready for rental! The style of the home offers a very attractive roof line with steep pitches, lots of balconies and being located West of Gulf drive there are no busy roads to cross and only a 1 minute …
      • Suitable for children - ask
      • Suitable for the elderly - ask

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      Reviews

      (1)

      Perfect introduction to anna Maria island!

      Left on Mar 15, 2015 for a stay in March 2015

      Everything in this house is top notch. We've rented lots of places in Florida, but this one is beautiful. Everything is brand new, furniture is all good quality, bedding is great. Everything is so pretty. A lot of thought and care went into decorating the house, from accents to furnishings to patio furniture. Televisions in every bedroom, plus family room and pool area. Yes, there's a tv outside…

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      $250

      3 BR / 2 BA / Sleeps 10

      1 / 14

      $250

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      Las Palmas

      3 BR / 2 BA / Sleeps 10 | Quick view

      Details

      Las Palmas 212 Palm Avenue Anna Maria, Fl. 34216 North-end location just a few minutes walk to Pine Ave and Gulf beaches! This lovely 3 bedroom 2 bath elevated home with private heated pool is situated in the heart of the island, centrally located to everything fun. Comfortable and charming with a Southern-style …
      • Outdoor Pool
      • Internet Access
      • Dishwasher
      • Suitable for children - ask
      • Suitable for the elderly - ask

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      $156

      2 BR / 1 BA / Sleeps 6

      9 Reviews

      $156

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      Blue Dolphin Inn - Skimmer Down

      2 BR / 1 BA / Sleeps 6 | Quick view
      “ Very Good ” 9 Reviews

      Details

      Reviews

      (9)

      The Skimmer unit at the Blue Dolphin Inn, located at 404 Alamanda in the Historic Village of Anna Maria is a wonderful two bedroom, one bath downstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with fountains and nearby tiki table. The Blue …
      • Shared outdoor pool (unheated)
      • Internet Access
      • Grill
      • Pet friendly - ask
      • Smoking allowed - ask
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      Details

      Reviews

      (9)

      relaxing

      Left on Oct 01, 2010 for a stay in August 2010

      great time ok ok ok ok ok ok ok ok ok ok ok ok ok ok ok ok ok ok ok ok

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      $150

      2 BR / 2 BA / Sleeps 6

      1 Reviews

      $150

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      BLUE LAGOON NORTH

      2 BR / 2 BA / Sleeps 6 | Quick view
      “ Very Good ” 1 Reviews

      Details

      Reviews

      (1)

      Completely remodeled 2 bedroom/2 bath duplex, with a beautiful tropical HEATED pool, just over a block to the beach, and the free island Trolley! There is a King and a Queen bedroom in the North Unit, and a King and Twin Bedroom in the south unit. Both units also have a queen sleeper sofa.. 708 Sq. ft. 76 North …
      • Internet Access
      • Washing Machine
      • Clothes Dryer
      • Outdoor Dining Area
      • A/C or climate control
      • Suitable for children
      • Suitable for the elderly

      Details

      Reviews

      (1)

      Great Location

      Left on Dec 31, 2014 for a stay in October 2014

      BLN is very well located in the quieter northern part of the island. It is just a very short walk from the beach and Ginny and Jane Es. Likewise, a short walk in the opposite direction to the shops and restarants on Pine. The unit itself, while it doesn't look anything special from the outside, is very pleasant on the inside and surprisingly spacious, but don't expect 5 star luxury.

      One note …

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      $143

      3 BR / 3 BA / Sleeps 8

      1 Reviews

      $143

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      Bay View Villa

      3 BR / 3 BA / Sleeps 8 | Quick view
      “ Excellent ” 1 Reviews

      Details

      Reviews

      (1)

      Bay View Villa is a three bedroom, three bath private Key West style island home with bay views; tile and bamboo floors, spacious living room with large open decks, and just a short stroll to Bean Point and Bayfront Park. Very desireable area on the North end of Anna Maria Island. Sleeps upto 8 people. Amenities …
      • Internet Access
      • Washing Machine
      • Clothes Dryer
      • A/C or climate control
      • Central heating
      • Suitable for children

      Details

      Reviews

      (1)

      quiet ,spacious,clean ,lovely position

      Left on Dec 02, 2011 for a stay in November 2011

      everything spot on,between the 2 piers ,both walking distance,2 minutes stroll to the park opposite with the beach ,sea and picnic area,lovely. a clean peacefull area .

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      $170

      3 BR / 2 BA / Sleeps 6

      1 / 16

      $170

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      Jacaranda Artist Retreat

      3 BR / 2 BA / Sleeps 6 | Quick view

      Details

      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 sugar-sand beach. You can …
      • Wireless Internet
      • Washing Machine
      • Clothes Dryer
      • Outdoor Dining Area
      • A/C or climate control
      • Pet friendly - ask
      • Suitable for children - over five
      • Suitable for the elderly - ask

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      $243

      4 BR / 3 BA / Sleeps 8

      1 Reviews

      $243

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      North Shore Villa Anna Maria

      4 BR / 3 BA / Sleeps 8 | Quick view
      “ Very Good ” 1 Reviews

      Details

      Reviews

      (1)

      NORTH SHORE VILLA 904 North Shore Drive Anna Maria Welcome to North Shore Villa. This luxury Key West style home has it all. Expansive bay views, private heated pool, extra large master suite with a double shower and Jacuzzi tub, fresh and modern decor, two large balconies, indoor sitting area off the pool, and 2 …
        • Suitable for children
        • Suitable for the elderly - ask

        Details

        Reviews

        (1)

        Great house- Poor Management

        Left on Jan 05, 2015 for a stay in December 2014

        In August I reserved N. Shore house for 2 weeks - Our family's Christmas- 6 adults. Final deposit due early December. The Home is as described-- very beautiful, casual feel, plenty of room, so clean and well kept. Loved It!

        On the 1st Monday of our trip a construction crew pulled up to house next door. (Scaffolding and construction limber etc was already on the property.) There were 5-7 …

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        $200

        3 BR / 2 BA / Sleeps 6

        1 / 17

        $200

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        Casa Allegria

        3 BR / 2 BA / Sleeps 6 | Quick view

        Details

        Casa Allegria is just perfect! Beautiful cool beachy colors throughout and only a short walk from the beach. This spacious 3 bedroom, 2 bath ground level home is located in the most sought after area on Anna Maria Island! Close to Pine Avenue, trolley stops, and the SandBar Restaurant. Come and enjoy the island life…
          • Suitable for children
          • Suitable for the elderly

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          $157

          2 BR / 2 BA / Sleeps 6

          1 / 24

          $157

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          Cook's Cove: 2BR Elderly-Friendly Steps From Beach

          2 BR / 2 BA / Sleeps 6 | Quick view

          Details

          Grab your flip flops and your bathing suit for your fabulous vacation in this well-appointed Anna Maria home! Cook's Cove is located just steps away from the beautiful, white sand beaches of Anna Maria Island and the azure water of the Gulf of Mexico. Both elderly- and family-friendly, this lovely, two-bedroom, 2.5-…
          • Internet Access
          • Fireplace
          • Washing Machine
          • Clothes Dryer
          • A/C or climate control
          • Suitable for children - over five
          • Suitable for the elderly

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          $343

          4 BR / 3 BA / Sleeps 10

          1 / 40

          $343

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          LA HACIENDA

          4 BR / 3 BA / Sleeps 10 | Quick view

          Details

          Located in the heart of Anna Maria, a gorgeous and spacious Mediterranean style 4 Bedroom/3 Bath Home with a Heated Pool in a very private and peaceful setting. Only steps to Pine Avenue shopping and Trolley Stop, 2 blocks to the Beach, and walking distance to the Pier. The open floor plan features granite countertops…
          • Internet Access
          • Washing Machine
          • Clothes Dryer
          • Outdoor Dining Area
          • A/C or climate control
          • Suitable for children
          • Suitable for the elderly

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          $129

          2 BR / 1 BA / Sleeps 4

          2 Reviews

          $129

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          Light House: 2BR/1BA Canal-Front Home with Dock

          2 BR / 1 BA / Sleeps 4 | Quick view
          “ Very Good ” 2 Reviews

          Details

          Reviews

          (2)

          The Light House welcomes you in with its tropical landscaping, canal view and calming green exterior. This nicely furnished two-bedroom, one-bath vacation rental on Anna Maria Island has everything you need to begin a relaxing and restful vacation. Newer appliances will make quick work of breakfast or dinner, leaving…
          • Waterfront
          • Wireless Internet
          • Washing Machine
          • Clothes Dryer
          • A/C or climate control
          • Suitable for children - over five
          • Suitable for the elderly

          Details

          Reviews

          (2)

          Island Paradise

          Left on Jan 07, 2014 for a stay in December 2013

          One block from bay and four blocks from Gulf or Bean Point...what more could you want?!! Easy walk to all the restaurants and shopping on the North end of island (our favorite part of anna Maria). We brought our own bicycles and the garage was a good storage area for them.
          Loved the backyard view of the canal and the Florida room was excellent for dining in on those occassions.
          Cozy little …

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          $214

          3 BR / 2 BA / Sleeps 8

          2 Reviews

          $214

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          AMI Retreat: 3BR Pool Home 200 Steps from Beach

          3 BR / 2 BA / Sleeps 8 | Quick view
          “ Excellent ” 2 Reviews

          Details

          Reviews

          (2)

          Located in the city of Anna Maria on the north end of Anna Maria Island, this gorgeous three-bedroom dog-friendly vacation rental is the perfect place for a vacation retreat! With an estimated 2100 square feet, AMI Retreat has plenty of room to kick off your flip flops and enjoy your down time. With king beds in …
          • Wireless Internet
          • Washing Machine
          • Clothes Dryer
          • A/C or climate control
          • Patio
          • Pet friendly - ask
          • Suitable for children

          Details

          Reviews

          (2)

          Relaxing

          Left on Feb 14, 2015 for a stay in February 2015

          Our rental property was exactly how it was pictured on the web. Plenty of space with all the amenities you need to prepare food in our go out. The newly installed pool and spa made this rental perfect!

          The quick access to the beach allowed for many many walks on the white sand beach and plenty of time to enjoy food and cocktails at the sandbar restaurant

          I highly recommend this …

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          $186

          2 BR / 2 BA / Sleeps 4

          1 / 21

          $186

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          Tequila Sunset: 2BR Island Home with Heated Pool

          2 BR / 2 BA / Sleeps 4 | Quick view

          Details

          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 beach home with both…
          • Internet Access
          • Washing Machine
          • Clothes Dryer
          • A/C or climate control
          • Porch
          • Pet friendly
          • Suitable for children - over five
          • Suitable for the elderly - ask

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          $121

          1 BR / 1 BA / Sleeps 4

          4 Reviews

          $121

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          Island Place Cottage: 1BR Pet-Friendly Cottage

          1 BR / 1 BA / Sleeps 4 | Quick view
          “ Excellent ” 4 Reviews

          Details

          Reviews

          (4)

          This vacation rental is located on Anna Maria Island's historic Pine Avenue, halfway between the Gulf of Mexico and the Anna Maria City Pier! This adorable, one bedroom cottage, with high beamed ceilings, wood floors and shabby chic décor throughout is ideal for a vacation getaway! This quaint cottage offers a fully…
          • Internet Access
          • Washing Machine
          • Clothes Dryer
          • A/C or climate control
          • Parking
          • Pet friendly
          • Suitable for children - over five
          • Suitable for the elderly

          Details

          Reviews

          (4)

          Great cottage, great location.

          Left on Jul 26, 2013 for a stay in July 2013

          Cottage is perfectly located right in the heart of anna Maria. Quick walk to the Gulf beaches or to the Bay.

          Cottage was immaculate and perfect size for the three of us. A few years ago we stayed in the adjacent Pineapple House which was also perfect for our larger party during that visit.

          Would not hesitate to stay again.

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          $209

          4 BR / 3 BA / Sleeps 8

          1 / 30

          $209

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          Pelican Villa

          4 BR / 3 BA / Sleeps 8 | Quick view

          Details

          Pelican Villa 214 Magnolia Avenue Anna Maria, Fl. 34216 Pelican Villa is a newly constructed home on the prestigious north end of Anna Maria Island. You will find 4 bedrooms and 3 full bathrooms in this property. This building is an elevated home with a large covered patio area and a private heated pool, …
          • Outdoor Pool
          • Internet Access
          • Dishwasher
          • Suitable for children - ask
          • Suitable for the elderly - ask

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          $141

          2 BR / 1 BA / Sleeps 4

          3 Reviews

          $141

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          TURTLE TRAX

          2 BR / 1 BA / Sleeps 4 | Quick view
          “ Excellent ” 3 Reviews

          Details

          Reviews

          (3)

          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 master with TV, a Queen …
          • Internet Access
          • Washing Machine
          • Clothes Dryer
          • Outdoor Dining Area
          • A/C or climate control
          • Suitable for children
          • Suitable for the elderly

          Details

          Reviews

          (3)

          Great week at a great place

          Left on Aug 08, 2013 for a stay in April 2013

          We had a great visit in april. The weather was great, the pool was even better. Cannot wait to get back in 2014.

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          $145

          4 BR / 2 BA / Sleeps 8

          2 Reviews

          $145

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          Whispering Winds

          4 BR / 2 BA / Sleeps 8 | Quick view
          “ Excellent ” 2 Reviews

          Details

          Reviews

          (2)

          Whispering Winds 210 Sycamore Avenue Anna Maria, Fl 34216 Key West style 4 bedroom, 2 bath home just a short walk from the Gulf of Mexico. This home offers private heated pool, three covered decks overlooking pool, BBQ grill, two car garage, cathedral ceilings, tile, carpet, open floor plan with large kitchen…
          • Outdoor Pool
          • Internet Access
          • Dishwasher
          • Suitable for children - ask
          • Suitable for the elderly - ask

          Details

          Reviews

          (2)

          Can't wait to go BACK!

          Left on May 13, 2014 for a stay in March 2014

          We stayed at Whisper Winds,3 houses to the wonderful White Sand... Great house with 4 bdrm ,heated pool, great location with plenty of room for Family Vacation.. This is our 2nd trip to AnnaMaria. So many quaint shops,be sure you visit the fresh donuts shop..get their early their worth the wait. The north end is great if your traveling with small kids. Bring your bikes or rent them their.. So …

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          $111

          1 BR / 1 BA / Sleeps 2

          3 Reviews

          $111

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          SNAILS PACE

          1 BR / 1 BA / Sleeps 2 | Quick view
          “ Excellent ” 3 Reviews

          Details

          Reviews

          (3)

          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 provided kayaks right …
          • Internet Access
          • Washing Machine
          • Clothes Dryer
          • Outdoor Dining Area
          • A/C or climate control
          • Pet friendly
          • Suitable for children
          • Suitable for the elderly

          Details

          Reviews

          (3)

          It was perfectly amazing!

          Left on Nov 14, 2013 for a stay in November 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 and shops. We had such a wonderful time there and didn't want to leave after our week was over. The staff were very friendly and helpful, as were the locals that live in the area. They helped us with tips on where to eat …

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          $214

          3 BR / 2 BA / Sleeps 6

          1 / 23

          $214

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          Havana Cay

          3 BR / 2 BA / Sleeps 6 | Quick view

          Details

          Havana Cay 109 Cedar St. Anna Maria, Fl. 34216 With this secluded and historic property, you will feel like you are vacationing at your own private 5-star resort. Havana Cay sits only 4 houses in from the beach and there are no busy streets to cross and zipping to and from the beach will be so easy! A quick 30 …
          • Private Pool
          • High Speed Internet
          • Patio
          • Television
          • DVD Player
          • Suitable for children - ask
          • Suitable for the elderly - ask

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          $171

          3 BR / 2 BA / Sleeps 6

          5 Reviews

          $171

          Inquire

          Coastal Cottage: 3BR Pet-Friendly Pool Home

          3 BR / 2 BA / Sleeps 6 | Quick view
          “ Excellent ” 5 Reviews

          Details

          Reviews

          (5)

          The adorable Coastal Cottage, located in the laid-back city of Anna Maria, is the perfect place to take a totally carefree vacation. The white sand beach of Anna Maria Island and the azure blue waters of the Gulf of Mexico are only a short stroll from this delightful three-bedroom, two-bath vacation rental. An open …
          • Wireless Internet
          • Washing Machine
          • Clothes Dryer
          • A/C or climate control
          • Patio
          • Suitable for children - over five
          • Suitable for the elderly

          Details

          Reviews

          (5)

          Coastal Cottage

          Left on Jul 25, 2013 for a stay in February 2013

          We loved the location. We enjoyed the house, but we did not know it was up for sale until we pulled in the driveway. We had too many requests for viewing which disturbed our visit enough that we decided not to book with you again next year.

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          $214

          4 BR / 3 BA / Sleeps 8

          1 / 17

          $214

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          Sundown South

          4 BR / 3 BA / Sleeps 8 | Quick view

          Details

          Sundown South 300 N. Shore Unit A Anna Maria, Fl. 34216 This is a one of a kind brand new construction on Anna Maria Island. Sundown South has 4 bedrooms and 3 full baths and a private heated pool. Located on a beautiful lake on the prestigious North Shore Drive and only a very short walk to famous Pine Ave. It…
          • Private Pool
          • High Speed Internet
          • Patio
          • Television
          • DVD Player
          • Suitable for children - ask
          • Suitable for the elderly - ask

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          $300

          5 BR / 4 BA / Sleeps 12

          1 Reviews

          $300

          Inquire

          Villa Marianne

          5 BR / 4 BA / Sleeps 12 | Quick view
          “ Excellent ” 1 Reviews

          Details

          Reviews

          (1)

          Villa Marianne 111 Maple Ave. Anna Maria, Fl. 34216 Wow, you just can't say enough great things about this beautiful beach villa! This 5 bedroom, 4 bathroom home so close to the beach- no more than a 1 minute stroll and located on the prestigious North end of the island. Every room is exquisite- decorated to …
          • Outdoor Pool
          • Internet Access
          • Dishwasher
          • Suitable for children - ask
          • Suitable for the elderly - ask

          Details

          Reviews

          (1)

          Awesome place to stay!!

          Left on Mar 22, 2015 for a stay in March 2015

          We just returned from our week long stay at Villa Marianne and couldn't be happier. We were two families- mine and my cousin and hers. 4 adults total, and 5 kids ages 8,6, 4,3, and 1. First of all, you are just a short walk to a lovely stretch of beach. At the end of the street there is a short path. And since it isn't a public access area, there aren't that many people- even during crowded …

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          $343

          4 BR / 4 BA / Sleeps 11

          2 Reviews

          $343

          Inquire

          HAV'ANNA HIDEAWAY

          4 BR / 4 BA / Sleeps 11 | Quick view
          “ Excellent ” 2 Reviews

          Details

          Reviews

          (2)

          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 breakfast bar …
          • Internet Access
          • Washing Machine
          • Clothes Dryer
          • Outdoor Dining Area
          • A/C or climate control
          • Suitable for children
          • Suitable for the elderly

          Details

          Reviews

          (2)

          Fantastic Family vacation

          Left on Aug 02, 2013 for a stay in June 2013

          We rented Hava'nna Hideaway in June 2013. It was the first family vacation for all ten of us. The house was very clean and roomy so we didn't feel hemmed in. We cooked most of our meals and used the BBQ grill outside a lot. It's about a block from the beach but they provide a beach wagon to haul your stuff. We loved the small pool outside and we used it a lot just sitting around talking and …

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          $330

          5 BR / 3 BA / Sleeps 14

          1 / 24

          $330

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          Villa Del Sol

          5 BR / 3 BA / Sleeps 14 | Quick view

          Details

          Villa Del Sol 211 Chilson Avenue Anna Maria, FL 34217 This is an exquisite, newly remodeled 5 bedroom, 3 bath ground level home with available boat dock. Inside the home you will find quality furnishings with a Caribbean decor. The open floor plan provides the perfect space for spending time together or …
          • Outdoor Pool
          • Internet Access
          • Dishwasher
          • Suitable for children - ask
          • Suitable for the elderly - ask

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          $171

          2 BR / 2 BA / Sleeps 6

          4 Reviews

          $171

          Inquire

          Island Oasis: 2BR Canal Home with Pool and Dock

          2 BR / 2 BA / Sleeps 6 | Quick view
          “ Excellent ” 4 Reviews

          Details

          Reviews

          (4)

          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 two baths, with a …
          • Waterfront
          • Spa/Whirlpool
          • Internet Access
          • Washing Machine
          • Clothes Dryer
          • Pet friendly
          • Suitable for children - over five
          • Suitable for the elderly

          Details

          Reviews

          (4)

          Best Stay Yet!

          Left on Jul 11, 2013 for a stay in May 2013

          We were lucky to find Island Oasis. The wife and I have visited Siesta Key and anna Maria Island several times. This was the best stay yet. We caught snook across the bay in Perico Bayou and grouper at Longboat Pass. The backyard pool is the nicest and being able to hop in the boat and to the beach is just wonderful.

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          $145

          1 BR / 1 BA / Sleeps 4

          1 / 14

          $145

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          Hidden Oasis

          1 BR / 1 BA / Sleeps 4 | Quick view

          Details

          Hidden Oasis 777A North Shore Anna Maria, Fl. 24216 This lovely 1 bedroom, 1 bathroom gulf front hideaway has just been completely renovated from top to bottom! This second level location has a private balcony with large southern views of the beautiful blue waters of the Gulf of Mexico. Part of a Gulf-front …
          • Internet Access
          • Dishwasher
          • Suitable for children - ask
          • Suitable for the elderly - ask

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          $360

          5 BR / 3 BA / Sleeps 16

          1 / 24

          $360

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          Willow Beach House

          5 BR / 3 BA / Sleeps 16 | Quick view

          Details

          Willow Beach House 211 Willow Avenue Anna Maria, Fl 34216 Willow Beach House is a beautiful, bright and airy 5 bedroom and 3.5 bathroom private home, located on the prestigious North-end of Anna Maria. Only a block away from the stunning white sand beaches, this newly renovated canal front home offers a private …
            • Suitable for children - ask
            • Suitable for the elderly - ask

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            $175

            2 BR / 2 BA / Sleeps 4

            1 / 15

            $175

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            Windsong Cottage

            2 BR / 2 BA / Sleeps 4 | Quick view

            Details

            Windsong Cottage 119 Beach Avenue Anna Maria, Fl 34216 Windsong Cottage is a charming 2 bedroom 2 bath elevated home just five houses from the Gulf. It has an open floor plan with new, comfortable furnishings that make you feel *right at home*. The plantation shutters add to that "Old Florida" charm. You won'…
            • Outdoor Pool
            • Internet Access
            • Dishwasher
            • Suitable for children - ask
            • Suitable for the elderly - ask

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            $209

            4 BR / 4 BA / Sleeps 8

            1 Reviews

            $209

            Inquire

            Sunchase Villa

            4 BR / 4 BA / Sleeps 8 | Quick view
            “ Very Good ” 1 Reviews

            Details

            Reviews

            (1)

            Sunchase Villa 302 Gulf Blvd Anna Maria, Fl. 34216 Sunchase Villa is a true Old Florida, ground level beach cottage nestled on the north end of Anna Maria Island only a short walk to restaurants and shopping. There are fantastic Gulf Views from this well-appointed 4 bedroom, 4.5 bath private home directly across…
            • Internet Access
            • Suitable for children - ask
            • Suitable for the elderly - ask

            Details

            Reviews

            (1)

            Great location but property needs some improvements

            Left on Dec 15, 2014 for a stay in December 2014

            The location of this house is great---right on the beach and close to many restaurants! The house is roomy and nicely furnished, including multiple TVs for anyone who is interested. The screened-in porch looking out on the water is a real plus! However, the house needs some serious work. Many of the windows did not open, the kitchen cabinet doors kept falling open, one bathroom drain was clogged…

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            $200

            2 BR / 2 BA / Sleeps 6

            1 / 20

            $200

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            A Sandbox by the Sea

            2 BR / 2 BA / Sleeps 6 | Quick view

            Details

            A Sandbox by the Sea 507 Spring Avenue Anna Maria, FL 34216 A Sandbox by the Sea has a large luxurious tropical yard with a new private heated pool complete with tanning shelf and a bubbling spa tub!! Both water features have the option of digital light shows for evening fun! A press of a button allows you to …
            • Heated Pool
            • High Speed Internet
            • Patio
            • Television
            • DVD Player
            • Suitable for children - ask
            • Suitable for the elderly - ask

            PreviousNext property

            $200

            2 BR / 2 BA / Sleeps 6

            4 Reviews

            $200

            Inquire

            Starfish Dreams: 2BR Canal Home w/Dock and Pool

            2 BR / 2 BA / Sleeps 6 | Quick view
            “ Excellent ” 4 Reviews

            Details

            Reviews

            (4)

            Starfish Dreams is the perfect place to start your vacation! This family-friendly vacation rental is centrally located on Pine Avenue in the city of Anna Maria on Anna Maria Island, halfway between the Gulf of Mexico and Tampa Bay. If that were not enough, it also has a heated pool and is on a canal. This two-…
            • Waterfront
            • Internet Access
            • Washing Machine
            • Clothes Dryer
            • A/C or climate control
            • Suitable for children - over five
            • Suitable for the elderly - ask

            Details

            Reviews

            (4)

            Magnificent property in fantastic spot on Anna Maria

            Left on Jun 14, 2013 for a stay in May 2013

            This was the best holiday rental (sorry Sue) we've ever had. Right in Pine Street, where all of the boutiques and local stores are, but within 100 yards of the beach and City Pier. Fantastically appointed, with excellent quality of all the equipment, this is a really, really comfortable and well situated property.

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            $285

            3 BR / 2 BA / Sleeps 8

            15 Reviews

            $285

            Inquire

            Azure Seas

            3 BR / 2 BA / Sleeps 8 | Quick view
            “ Excellent ” 15 Reviews

            Details

            Reviews

            (15)

            The Azure Seas is a glorious three bedroom, two bath Gulf front home located at 779 North Shore Drive in the much desired and tranquil northern end of Anna Maria Island. Tropical paradise found!! This is the perfect place to forget your troubles and soak in the unbelievable views of the Gulf of Mexico. A large, 16 x …
            • Waterfront
            • Ocean or water views
            • Internet Access
            • Grill
            • Pet friendly
            • Smoking allowed - ask
            • Suitable for children - ask
            • Suitable for the elderly - ask
            • Wheelchair accessible - ask

            Details

            Reviews

            (15)

            great

            Left on Aug 05, 2010 for a stay in June 2010

            Totally sold my enlaws on the gulf coast beaches. Location perfect.

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            $350

            3 BR / 2 BA / Sleeps 9

            2 Reviews

            $350

            Inquire

            Seaside

            3 BR / 2 BA / Sleeps 9 | Quick view
            “ Excellent ” 2 Reviews

            Details

            Reviews

            (2)

            Seaside 851 N. Shore Dr. Anna Maria, Fl. 34216 Seaside is a private, luxury home located on the very northern tip of Anna Maria Island. It looks directly at the Skyway Bridge, Egmont Key and Downtown St. Petersburg- you will not find a more breathtaking view anywhere on the island. The home has the charm of a …
            • High Speed Internet
            • Patio
            • Television
            • DVD Player
            • Suitable for children - ask
            • Suitable for the elderly - ask

            Details

            Reviews

            (2)

            The most amazing views

            Left on Jul 20, 2013 for a stay in July 2013

            We love Anna Maria and decided to splurge and rent a house on the north end right on the beach. This was a winner, a 180 degree view of the gulf, sunrises from the master bedroom and sunsets all in one location. And the best view of the distant Skyway Bridge, this house had all the necessary things, great master suite, studio, loft, decks.....If I had to complain the two other bedrooms were a …

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            $223

            2 BR / 2 BA / Sleeps 6

            4 Reviews

            $223

            Inquire

            LAZY LAGOON

            2 BR / 2 BA / Sleeps 6 | Quick view
            “ Excellent ” 4 Reviews

            Details

            Reviews

            (4)

            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 the West Coast or …
            • Waterfront
            • Ocean or water views
            • Hot Tub/Jacuzzi
            • Internet Access
            • Washing Machine
            • Suitable for children
            • Suitable for the elderly

            Details

            Reviews

            (4)

            friendly retreat

            Left on Aug 14, 2013 for a stay in July 2013

            This was our 3rd visit to the island. we usually
            share with family but we travelled ourselves this
            year. Lazy Lagoon was a beautiful 2 bed canal
            home with pool. This smaller property offered
            everything the larger homes we previously rented had.
            My daughter (19) fished for hours every day even the
            rain did not bring her in. A lovely walk to the short
            walk to the beach and short walk to sand …

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            $188

            3 BR / 2 BA / Sleeps 8

            12 Reviews

            $188

            Inquire

            Blue Dolphin Inn - Flamingo Up

            3 BR / 2 BA / Sleeps 8 | Quick view
            “ Excellent ” 12 Reviews

            Details

            Reviews

            (12)

            The Flamingo unit at the Blue Dolphin Inn, located at 780 Jacaranda in the Historic Village of Anna Maria is a wonderful and spacious three bedroom, two bath upstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with fountains and nearby tiki …
            • Shared outdoor pool (unheated)
            • Internet Access
            • Grill
            • Pet friendly - ask
            • Smoking allowed - ask
            • Suitable for children - ask
            • Suitable for the elderly - ask
            • Wheelchair accessible - ask

            Details

            Reviews

            (12)

            Megan and Justin's Wedding

            Left on Oct 28, 2010 for a stay in October 2010

            This was the best vacation ever. I could not have wanted any more. The hammock between two palm trees, the pool, the wooden tower, it was just amazing. I didn't want to leave. Very clean, had everything we needed. Very impressed!

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            $379

            6 BR / 3 BA / Sleeps 17

            1 / 30

            $379

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            Grande Haven

            6 BR / 3 BA / Sleeps 17 | Quick view

            Details

            Grande Haven 804 North Shore Dr. Anna Maria, Fl. 34216 Grande Haven is a spectacular example of high architecture, fine design and custom finishing at its best. This home was designed by the award winning Gene Leedy, combining the use of pre-stressed concrete, contemporary architecture and a splash of British East…
            • High Speed Internet
            • Patio
            • Television
            • DVD Player
            • Suitable for children - ask
            • Suitable for the elderly - ask

            PreviousNext property

            $350

            5 BR / 4 BA / Sleeps 12

            1 / 28

            $350

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            Villa La Concha

            5 BR / 4 BA / Sleeps 12 | Quick view

            Details

            Villa La Concha 113 Maple Avenue Anna Maria, Fl 34216 Villa La Concha is a stunning brand new elevated and luxury Island home located on the prestigious Northern end of Anna Maria Island. This lovely home is located West of Gulf Drive and just 1 minute stroll down the street from a direct beach access to the Gulf …
              • Suitable for children - ask
              • Suitable for the elderly - ask

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              $124

              2 BR / 2 BA / Sleeps 6

              1 / 13

              $124

              Inquire

              Sunny Side Up

              2 BR / 2 BA / Sleeps 6 | Quick view

              Details

              Sunny Side-Up 267 Gladiolus Street Anna Maria, Fl. 34216 Trendy colorful, happy cottage located in popular Anna Maria City. This 2 bedroom 2 bath ground level home was completely renovated inside and out. All new furniture throughout with lots of fun decor and an island feel. A delight the moment you enter …
              • Internet Access
              • Dishwasher
              • Suitable for children - ask
              • Suitable for the elderly - ask

              PreviousNext property

              $250

              4 BR / 4 BA / Sleeps 10

              1 / 25

              $250

              Inquire

              Island Dream

              4 BR / 4 BA / Sleeps 10 | Quick view

              Details

              Island Dream 157 Crescent Drive Anna Maria, FL 34216 An exceptional property with glorious views of the Sunshine Skyway Bridge from its entrance, this beautiful, newly built and elegantly furnished four bedroom and four bathroom home on the desirable north end of Anna Maria is situated in a quiet residential …
              • Private Pool
              • High Speed Internet
              • Patio
              • Television
              • DVD Player
              • Suitable for children - ask
              • Suitable for the elderly - ask

              PreviousNext property

              $250

              4 BR / 3 BA / Sleeps 10

              1 / 22

              $250

              Inquire

              Bay View

              4 BR / 3 BA / Sleeps 10 | Quick view

              Details

              Bay View 804 South Bay Blvd. Anna Maria, Fl 34216 Stunning Bay views and white sandy beaches are literally at your doorstep at Bay View. This spacious, well-equipped four bedroom, three-bath ground-level property provides all the comforts of home in an ideal beach setting. It has been recently completely …
              • Internet Access
              • Dishwasher
              • Suitable for children - ask
              • Suitable for the elderly - ask
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