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$209

4 BR / 3 BA / Sleeps 10

Sundown North - Anna Maria vacation rentals
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$209

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Sundown North

Anna Maria house
4 BR / 3 BA / Sleeps 10 | Quick view

Details

Sundown North 300 N. Shore Dr. - Unit B Anna Maria, Fl. 34216 Sundown North- a unique water front property that has 4 bedrooms, 3 bathrooms and a private heated pool one block to Pine Ave. It sleeps up to 8 guests in beds and 10 total. Sundown North also has a separate living room upstairs with large TV and …
  • Private Pool
  • High Speed Internet
  • Patio
  • Television
  • DVD Player
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$223

2 BR / 2 BA / Sleeps 6

4 Reviews

$223

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LAZY LAGOON

Anna Maria house
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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$132

2 BR / 2 BA / Sleeps 8

1 Reviews

$132

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Grant's View - 412 S Bay Blvd

Anna Maria house
2 BR / 2 BA / Sleeps 8 | Quick view
“ Poor ” 1 Reviews

Details

Reviews

(1)

This bay front private home is on Tampa Bay and you will enjoy the views of the water not to mention Dolphins swimming by. The bayfront is furnished with beach style furniture which offers a rich and comfortable atmosphere and is fully furnished with all comforts of home for a worry-free holiday; virtually everything…
  • Internet Access
  • Parking
  • Dishwasher
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Location the only good thing

Left on Nov 03, 2014 for a stay in October 2014

This house has great location and that's about it. Sorry to say the place needs updating, needs to have more furnishings,like dishes and pots and pans etc....furniture was cheap and old. The place smelled musty and had cockroaches, dead and alive. No hot water in master shower and the shower door was about to fall off the track. Outlet in bedroom was hanging out of the wall and the cleaning crew…

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$471

4 BR / 3 BA / Sleeps 8

4 Reviews

$471

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Cherryfish, a spectacular spacious 4-bed home!

Anna Maria villa
4 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 4 Reviews

Details

Reviews

(4)

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. Climb the steps of this…
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children

Details

Reviews

(4)

Wonderful, chilled out experience!

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

Cherryfish is a beautiful home in a tranquil setting on anna Maria Island. The house is close to the beach and close to the "village centre" and probably the best restaurant on the island. The whole place has a very laid back feel and Cherryfish is the perfect house to stay and experience the anna Maria way of life.

The house is well equipped, although a few more instructions on how to use some …

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$400

5 BR / 3 BA / Sleeps 15

Lighthouse Lagoon - Anna Maria vacation rentals
1 / 31

$400

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Lighthouse Lagoon

Anna Maria house
5 BR / 3 BA / Sleeps 15 | Quick view

Details

Lighthouse Lagoon 508 Spring Avenue Anna Maria, Fl. 34216 Lighthouse Lagoon is a beautifully updated 5 bedroom, 3 bathroom Island home located on Spring Street on the North-end of Anna Maria Island. The rear of the house backs up to outstanding Pine Avenue with it's quaint shops, wonderful restaurants and of …
  • Private Pool
  • High Speed Internet
  • Patio
  • Television
  • DVD Player
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$244

3 BR / 2 BA / Sleeps 8

HAV'ANNA DAYDREAMIN - Anna Maria vacation rentals
1 / 30

$244

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HAV'ANNA DAYDREAMIN

Anna Maria house
3 BR / 2 BA / Sleeps 8 | Quick view

Details

Completely Remodeled 3 bedroom/2 bath home with private Heated pool. Beautiful new tile, Granite countertops, all new appliances, and living room overlooking the heated pool. Bright, open kitchen, dining and living area! Sleeps up to 8. 1500 Sq. ft. 204 Archer Way, Anna Maria 3 Bedroom/2Bath Home with Heated Pool…
  • 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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$214

3 BR / 2 BA / Sleeps 6

1 / 23

$214

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Havana Cay

Anna Maria house
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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$300

4 BR / 3 BA / Sleeps 14

1 Reviews

$300

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Ocean Walk

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

Details

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

    Details

    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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    $350

    5 BR / 4 BA / Sleeps 12

    1 / 28

    $350

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    Villa La Concha

    Anna Maria house
    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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      $274

      4 BR / 2 BA / Sleeps 8

      6 Reviews

      $274

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      HAWAIIAN PUNCH

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

      Details

      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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      $250

      3 BR / 3 BA / Sleeps 6

      1 Reviews

      $250

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      Anna Maria Cottage

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

      Details

      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

        Details

        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

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

        Details

        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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        $188

        3 BR / 2 BA / Sleeps 8

        12 Reviews

        $188

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        Blue Dolphin Inn - Flamingo Up

        Anna Maria condo
        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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        $200

        3 BR / 2 BA / Sleeps 8

        1 / 19

        $200

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        Anna Maria Chateau

        Anna Maria house
        3 BR / 2 BA / Sleeps 8 | Quick view

        Details

        Anna Maria Chateau 612 Fern Street Anna Maria, Fl 34216 Perfect island getaway, nestled at the North end of Anna Maria Island. Anna Maria Chateau, open and spacious, a newly and completely renovated, well equipped 3 bedroom, 2 bath home with vaulted ceilings in the living area and in all bedrooms. This house has …
          • Suitable for children - ask
          • Suitable for the elderly - ask

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          $150

          2 BR / 2 BA / Sleeps 6

          1 Reviews

          $150

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          BLUE LAGOON NORTH

          Anna Maria condo
          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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          $257

          3 BR / 2 BA / Sleeps 8

          1 Reviews

          $257

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          OURPLACEBYTHESEA

          Anna Maria house
          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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          $141

          2 BR / 1 BA / Sleeps 5

          1 Reviews

          $141

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          YELLOWBIRD COTTAGE B

          Anna Maria cottage
          2 BR / 1 BA / Sleeps 5 | Quick view
          “ Excellent ” 1 Reviews

          Details

          Reviews

          (1)

          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 Washer/Dryer, Cable TV, …
          • 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

          (1)

          Very close to the beach

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

          Excellent service, from booking to checking into Yellowbird B. The cottage was lovely and clean and had everything we needed to enjoy our stay, including chairs for the beach.
          Brilliant location only a few steps from the lovely sandy beach.
          Only negative bathroom although very clean could do with an update.
          We had a fantastic holiday and hope to come back.

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          $225

          4 BR / 2 BA / Sleeps 10

          1 / 15

          $225

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          Whispering Whale Retreat

          Anna Maria house
          4 BR / 2 BA / Sleeps 10 | Quick view

          Details

          Whispering Whale Retreat 505 Spring Avenue, Anna Maria, Fl 34216 Whispering Whale Retreat is a lovely brand new elevated home with 4 bedrooms and 2 bathrooms. Located on the prestigious Northern end of Anna Maria Island this versatile home incorporates the best of all that Anna Maria Island has to offer! With a …
          • Outdoor Pool
          • Internet Access
          • Dishwasher
          • Suitable for children - ask
          • Suitable for the elderly - ask

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          $171

          3 BR / 2 BA / Sleeps 7

          1 / 21

          $171

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          The Beach House

          Anna Maria house
          3 BR / 2 BA / Sleeps 7 | Quick view

          Details

          The Beach House 9308 Gulf Drive Anna Maria, Fl. 34216 Totally updated 3 bedroom 2.5 bath elevated home just six houses from the Gulf of Mexico. French doors and sliders open to your covered wrap-around porches. Listen to the sounds of rustling palms and embrace the gentle gulf breezes while relaxing on your …
          • Internet Access
          • Dishwasher
          • Suitable for children - ask
          • Suitable for the elderly - ask

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          $300

          5 BR / 3 BA / Sleeps 10

          1 / 26

          $300

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          Whitecaps

          Anna Maria house
          5 BR / 3 BA / Sleeps 10 | Quick view

          Details

          Whitecaps 749 Jacaranda Anna Maria, FL 34217 Whitecaps is a luxury tropical island style 5 bedroom, 3.5 bathroom home located at the prestigous north end of Anna Maria Island. This home sits only 1 block in from the Gulf beaches and is only about a 1 minute stroll over to the water. It has wonderful views of…
          • Outdoor Pool
          • Dishwasher
          • Suitable for children - ask
          • Suitable for the elderly - ask

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          $171

          2 BR / 2 BA / Sleeps 6

          4 Reviews

          $171

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          Island Oasis: 2BR Canal Home with Pool and Dock

          Anna Maria house
          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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          $124

          2 BR / 2 BA / Sleeps 6

          1 / 13

          $124

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          Sunny Side Up

          Anna Maria house
          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

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          $156

          2 BR / 1 BA / Sleeps 6

          9 Reviews

          $156

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          Blue Dolphin Inn - Skimmer Down

          Anna Maria condo
          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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          $143

          2 BR / 2 BA / Sleeps 4

          1 Reviews

          $143

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          Birds Eye View

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

          Details

          Reviews

          (1)

          Birds Eye View 802 Gladiolus Street Anna Maria, FL 34216 This spacious and charming 2 bedroom, 2.5 bath elevated home is just three houses from the Gulf of Mexico! It is located near popular Bean Point at the prestigious northern tip of Anna Maria Island. It has fabulous island style furnishings and a bright open …
          • Dishwasher
          • Suitable for children - ask
          • Suitable for the elderly - ask

          Details

          Reviews

          (1)

          Nice Location - Bean Point

          Left on Sep 06, 2013 for a stay in September 2013

          Lovely property...close to both gulf and bay beaches for sunrise/sunset. Loads of space with a huge master bedroom/bathroom. Clean and well kept but could use a few updates. Toaster looked 1960's vintage and although it worked well enough, we were a bit concerned using it due to it's age. Oven door and oven itself were tricky to operate. Several of the venetian blinds did not work, either to open…

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          $250

          4 BR / 4 BA / Sleeps 10

          1 / 25

          $250

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          Island Dream

          Anna Maria house
          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

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          $209

          4 BR / 3 BA / Sleeps 8

          1 / 30

          $209

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          Pelican Villa

          Anna Maria house
          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 5

          1 / 30

          $141

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          YELLOWBIRD COTTAGE A

          Anna Maria cottage
          2 BR / 1 BA / Sleeps 5 | Quick view

          Details

          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 Washer/Dryer, Cable TV, …
          • Internet Access
          • Washing Machine
          • Clothes Dryer
          • Outdoor Dining Area
          • A/C or climate control
          • Pet friendly
          • Suitable for children
          • Suitable for the elderly

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          $175

          2 BR / 2 BA / Sleeps 4

          1 / 15

          $175

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          Windsong Cottage

          Anna Maria house
          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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          $170

          3 BR / 2 BA / Sleeps 6

          1 / 16

          $170

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          Jacaranda Artist Retreat

          Anna Maria house
          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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          $350

          3 BR / 2 BA / Sleeps 9

          3 Reviews

          $350

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          Seaside

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

          Details

          Reviews

          (3)

          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

          (3)

          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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          $200

          3 BR / 2 BA / Sleeps 6

          1 / 18

          $200

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          White Sands

          Anna Maria house
          3 BR / 2 BA / Sleeps 6 | Quick view

          Details

          White Sands 709 North Bay Blvd Anna Maria, Fl 34216 White Sands is a newly renovated beach cottage located on the prestigious Northern end of Anna Maria Island. Offering 3 bedrooms and 2 bathrooms, a new kitchen and a private heated pool this home is ideal for your Island getaway! Lots of attention to detail has …
            • Suitable for children - ask
            • Suitable for the elderly - ask

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            $214

            3 BR / 2 BA / Sleeps 8

            3 Reviews

            $214

            Inquire

            AMI Retreat: 3BR Pool Home 200 Steps from Beach

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

            Details

            Reviews

            (3)

            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

            (3)

            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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            $190

            3 BR / 2 BA / Sleeps 6

            1 / 14

            $190

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            Dolphin Dreams

            Anna Maria house
            3 BR / 2 BA / Sleeps 6 | Quick view

            Details

            Dolphin's Dream 855 North Shore Drive Anna Maria, Fl. 34216 Dolphin's Dream is a totally updated Florida beach house ideal for those who want Old Florida charm with updated decor. This 3 bedroom 2 bath ground level home is a short walk to the Rod-n-Reel Pier and Bean Point on the Gulf of Mexico. Incredible views of…
            • Internet Access
            • Dishwasher
            • Suitable for children - ask
            • Suitable for the elderly - ask

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            $186

            2 BR / 2 BA / Sleeps 4

            1 / 21

            $186

            Inquire

            Tequila Sunset: 2BR Island Home with Heated Pool

            Anna Maria house
            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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            $214

            4 BR / 3 BA / Sleeps 8

            1 / 17

            $214

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            Sundown South

            Anna Maria house
            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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            $209

            4 BR / 4 BA / Sleeps 8

            1 Reviews

            $209

            Inquire

            Sunchase Villa

            Anna Maria house
            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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            $330

            5 BR / 3 BA / Sleeps 14

            1 / 24

            $330

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            Villa Del Sol

            Anna Maria house
            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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            $290

            5 BR / 3 BA / Sleeps 12

            6 Reviews

            $290

            Book

            Gorgeous views,spectacular home!

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

            Details

            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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            $171

            3 BR / 2 BA / Sleeps 6

            5 Reviews

            $171

            Inquire

            Coastal Cottage: 3BR Pet-Friendly Pool Home

            Anna Maria house
            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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            $843

            4 BR / 4 BA / Sleeps 14

            5 Reviews

            $843

            Inquire

            Golden Dolphin

            Anna Maria house
            4 BR / 4 BA / Sleeps 14 | Quick view
            “ Excellent ” 5 Reviews

            Details

            Reviews

            (5)

            The Golden Dolphin, located at 801 North Shore Drive in Anna Maria, is the ultimate in beach front luxury. This executive level gulf front home has a tropical heated pool with waterfalls, four bedrooms, a library, three and one half baths a gourmet kitchen and much more. It was custom built with extreme attention to …
            • Waterfront
            • Ocean or water views
            • 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)

            An Excellent Vacation

            Left on Jun 16, 2013 for a stay in June 2013

            Our vacation was one of the best ever. A Golden Dolphin is a premier vacation property, and the location is phenomenal. We enjoyed the house and felt it offered more than we expected in amenities. Beach accessories were available at the house and contributed to our days on the beach. Anna Maria Island is a perfect vacation location with many attractions and fine restaurants. We are already …

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            $141

            2 BR / 1 BA / Sleeps 4

            3 Reviews

            $141

            Inquire

            TURTLE TRAX

            Anna Maria condo
            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

            Inquire

            Whispering Winds

            Anna Maria house
            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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            $285

            3 BR / 2 BA / Sleeps 8

            15 Reviews

            $285

            Inquire

            Azure Seas

            Anna Maria house
            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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            $157

            2 BR / 2 BA / Sleeps 6

            1 / 24

            $157

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

            Anna Maria house
            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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            $145

            1 BR / 1 BA / Sleeps 4

            1 / 14

            $145

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            Hidden Oasis

            Anna Maria house
            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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            $190

            2 BR / 2 BA / Sleeps 10

            18 Reviews

            $190

            Inquire

            Anna Maria Escape

            Anna Maria house
            2 BR / 2 BA / Sleeps 10 | Quick view
            “ Very Good ” 18 Reviews

            Details

            Reviews

            (18)

            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

            (18)

            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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            $157

            2 BR / 1 BA / Sleeps 6

            7 Reviews

            $157

            Inquire

            Pineapple Cottage: 2BR Quaint Pet-Friendly Cottage

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

            Details

            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

            Details

            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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            $200

            3 BR / 2 BA / Sleeps 6

            1 / 17

            $200

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            Casa Allegria

            Anna Maria house
            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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              $189

              3 BR / 2 BA / Sleeps 7

              8 Reviews

              $189

              Inquire

              BON AMI: 3BR Family- and Pet-Friendly Pool Home

              Anna Maria house
              3 BR / 2 BA / Sleeps 7 | Quick view
              “ Excellent ” 8 Reviews

              Details

              Reviews

              (8)

              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 open. Granite …
              • Wireless Internet
              • Washing Machine
              • Clothes Dryer
              • A/C or climate control
              • Deck
              • Pet friendly
              • Suitable for children - over five
              • Suitable for the elderly - ask

              Details

              Reviews

              (8)

              This was a return home for our family without any of the stress

              Left on Jul 24, 2013 for a stay in July 2013

              Coastal Cottages aMI staff is the best! The rental was truly more than we could have hoped for with central access to the Bay, Coast and lazy shopping. The North Shore is the only place we ever wish to return.

              The BON aMI home was just that, we needed for nothing during our stay. The freedom to kick our feet up, fish, swim, explore is all right there. This is what I remember of my childhood …

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              $125

              3 BR / 2 BA / Sleeps 6

              1 / 10

              $125

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              Sunset Cottage On Rose

              Anna Maria house
              3 BR / 2 BA / Sleeps 6 | Quick view

              Details

              Sunset Cottage on Rose 710 Rose Street Anna Maria, FL 34216 Sunset Cottage on Rose is a beautiful newly renovated Island home located on the prestigious Northern End of Anna Maria Island! Tucked away on a quiet residential street this wonderful property is your home away from home. With just a short walk to the …
                • Suitable for children - ask
                • Suitable for the elderly - ask
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