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$350

5 BR / 3 BA / Sleeps 15

Lighthouse Lagoon - Anna Maria vacation rentals
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Lighthouse Lagoon

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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$343

4 BR / 4 BA / Sleeps 11

2 Reviews

$343

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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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$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

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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$240

3 BR / 3 BA / Sleeps 6

LOVESHACK - Anna Maria vacation rentals
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$240

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LOVESHACK

3 BR / 3 BA / Sleeps 6 | Quick view

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Newly Remodeled 3 Bedroom/3 Bath with Queen Master, Queen 2nd Bedroom, and Twin Bunk Bed with Twin Trundle. New Pool and landscape, with a quiet canalfront setting. Located on a quiet dead end street, close to the trolley, the beach, the city pier, and walking distance to Anna Maria shops and restaurants. Amenities…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

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$300

3 BR / 3 BA / Sleeps 8

Heron House - Anna Maria vacation rentals
1 / 26

$300

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Heron House

3 BR / 3 BA / Sleeps 8 | Quick view

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Heron House 213 Elm Ave. Anna Maria, Fl. 34216 Wow, this luxury 3/3 North-end elevated home has it all! Just newly remodeled and ready to go! Just a short walk to it all- the beautiful Gulf beach, the fun and entertainment of Pine Ave. and even walk to the fantastic Sandbar restaurant. The home has approx. 2700 …
  • Internet Access
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

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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 / 6

$300

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Ocean Walk

4 BR / 3 BA / Sleeps 14 | Quick view

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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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    $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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    $129

    2 BR / 2 BA / Sleeps 6

    1 / 25

    $129

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    Casa Nana

    2 BR / 2 BA / Sleeps 6 | Quick view

    Details

    Enjoy an old fashioned Florida beach vacation at this wonderful cottage just 4 houses from the beach! One Florida family has spent over four decades building happy summer memories right in this spot, and they invite you to create some of your own treasured moments on your next visit to Anna Maria. Located right in …
    • Internet Access
    • A/C or climate control
    • Patio
    • Fitness Room
    • Parking
    • Suitable for children - ask
    • Suitable for the elderly - ask

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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

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    $129

    3 BR / 2 BA / Sleeps 8

    1 Reviews

    $129

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    Gulfshore Cottage: 3BR Family-Friendly, Block from Beach

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

    Details

    Reviews

    (1)

    Your time on Anna Maria Island should be perfectly charming in this classic beach-style cottage perfectly located on the west side of Gulf Drive in the city of Anna Maria. Only steps away from the azure blue waters of the Gulf of Mexico, this unique vacation rental boasts two very large bedrooms with king-sized bed …
    • Wireless Internet
    • Washing Machine
    • Clothes Dryer
    • A/C or climate control
    • Porch
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (1)

    This is fabulous, spacious and well equipped cottage in a superb location only 3 minutes walk from

    Left on Nov 12, 2014 for a stay in October 2014

    On entering the cottage, the screened porch was a perfect cool place to relax in the evening with a drink or to take morning coffee and watch Anna Maria Island come to life.

    Inside,, was spacious and open plan with a very well equipped and stocked kitchen , and comfortable seating and dining areas,simply decorated in restful paste; tones with 'beach themed' soft furnishings. This carried …

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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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    $143

    2 BR / 2 BA / Sleeps 4

    1 Reviews

    $143

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    Birds Eye View

    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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    $124

    2 BR / 2 BA / Sleeps 6

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    $124

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    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

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    $141

    2 BR / 1 BA / Sleeps 5

    1 Reviews

    $141

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    YELLOWBIRD COTTAGE B

    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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    $309

    4 BR / 3 BA / Sleeps 8

    2 Reviews

    $309

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    NORTH END CHIC

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

    Details

    Reviews

    (2)

    Beautiful, Brand New, Ground Level 4 bedroom/3 bath home, just around the corner from the Rod & Reel Pier, Bayfront Park, and just a couple of blocks to Fabulous Bean Point Beaches and Sunsets. Beautiful back yard with Heated Pool surrounded by a large paver deck and beautiful outdoor lounging area by pool. Open …
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • A/C or climate control
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (2)

    Slice of heaven

    Left on Oct 06, 2013 for a stay in October 2013

    This was our sixth visit to anna Maria Island and by far the best because of the house. It was wonderful in every way possible, immaculate, beautifully decorated, comfortable beds and quiet. Ami accommodations are easy to work with and very quick to answer my questions prior to arriving and when we checked in. We went to the Rod and Reel for supper one night which as always was excellent and went…

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    $317

    4 BR / 3 BA / Sleeps 9

    2 Reviews

    $317

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    TOES IN THE WATER

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

    Details

    Reviews

    (2)

    Newly remodeled, 4 bedroom/3 bath home, just 90 Steps to the beach, with a large private HEATED pool! Quiet setting in the beautiful north end of Anna Maria, and located west of Gulf Drive for easy beach access with no streets to cross. Easy walking distance to many shops and restaurants, and less than a block to …
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • A/C or climate control
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (2)

    Great location, adorable and clean!

    Left on Oct 27, 2013 for a stay in January 2013

    My parent rented this house when they came to visit last winter. We stayed for a week in late January(?) to early Feb and my 3 year old son still asks to go back.

    Personally I think that speaks volumes as 1. He is young 2. We have stayed/visited some amazing places since then. He doesn't ask to go to Disney World, he wants to go to 'his' beach house.

    It may look small from the front, but it …

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    $272

    3 BR / 3 BA / Sleeps 8

    1 Reviews

    $272

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    Canal Place

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

    Details

    Reviews

    (1)

    Canal Place is a restored three bedroom, three bath Old Florida island home with a pool and hot tub; neutral and relaxing decor with a spacious living room and just a short stroll to the white sand beaches if Anna Maria. Direct waterfront with beautiful canal views. Sleeps upto 8 people. Amenities Include: Full …
    • Waterfront
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Internet Access
    • Washing Machine
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (1)

    Great house for a family beach vacation!

    Left on Oct 30, 2013 for a stay in October 2013

    We stayed here for a week in October with seven of us and had a great time! The house was incredibly well equipped-the kitchen was stocked with lots of plates, bowls, glasses, pans, etc. which is really helpful when there are seven of us eating together everyday and there are lots of beach towels, beach chairs, and various other beach supplies right there. We used the bikes every day and it was …

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    $450

    3 BR / 2 BA / Sleeps 8

    1 Reviews

    $450

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    Serendipity

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

    Details

    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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    $244

    3 BR / 2 BA / Sleeps 8

    1 / 30

    $244

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    HAV'ANNA DAYDREAMIN

    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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    $125

    3 BR / 2 BA / Sleeps 6

    1 / 10

    $125

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    Sunset Cottage On Rose

    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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      $240

      3 BR / 2 BA / Sleeps 6

      2 Reviews

      $240

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      ANNA BANANA

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

      Details

      Reviews

      (2)

      Great Ground Level 3 Bedroom/2 Bath Home with a Heated Pool located in the quiet north end and just 3 houses to the beach!! King-Sized master bedroom with TV, Queen in the 2nd Bedroom with TV, and Twins in the Third with TV. Cable TV, DVD, and Flat Screen TV in Living Room. High speed Internet, Washer/Dryer, AC, Gas …
      • Internet Access
      • Washing Machine
      • Clothes Dryer
      • Outdoor Dining Area
      • A/C or climate control
      • Suitable for children
      • Suitable for the elderly

      Details

      Reviews

      (2)

      clean, cozy, and close to everything we need!

      Left on Aug 22, 2013 for a stay in July 2013

      Anna Banana house was pristinely clean, well-decorated, cozy, had plenty of room for the 4 of us, and was the most convenient place we have ever stayed on anna Maria Island. It is close to a lovely stretch of beach where we found fewer people and lots of relaxation...not to mention sand dollars, and lovely shells of all sorts. It is convenient to the trolley stops on Pine, and located on a …

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      $250

      4 BR / 3 BA / Sleeps 10

      1 / 25

      $250

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      Tarpon Pointe

      4 BR / 3 BA / Sleeps 10 | Quick view

      Details

      Tarpon Pointe 306 Tarpon St. Anna Maria, Fl. 34216 Tarpon Pointe is a newly remodeled property on the exclusive Northern-End of Anna Maria Island! This gorgeous private home embodies all of the best that the Island has to offer including a private heated pool, a dock, several porches, tropical landscaping and …
      • Heated Pool
      • High Speed Internet
      • Patio
      • Television
      • DVD Player
      • Suitable for children - ask
      • Suitable for the elderly - ask

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      $186

      2 BR / 2 BA / Sleeps 6

      7 Reviews

      $186

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      Whispering Pines: 2BR Classic Cottage Near Beach

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

      Details

      Reviews

      (7)

      This two-bedroom, two-bath vacation rental is located on the quiet north end of Anna Maria Island. Whispering Pines is just three houses from one of the most beautiful beach accesses on the island. This classic 1920's beach cottage has been lovingly restored. The original wood molding, fireplace, high ceilings, and …
      • Internet Access
      • Fireplace
      • Washing Machine
      • Clothes Dryer
      • A/C or climate control
      • Suitable for children - over five
      • Suitable for the elderly

      Details

      Reviews

      (7)

      Perfect Old Florida

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

      Whispering Pines has everything you could possibly want in an aMI vacation rental home with the exception of swimming pool, but who needs a pool when you are fifty yards from beach access and the Gulf?

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      $236

      3 BR / 2 BA / Sleeps 8

      1 / 18

      $236

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      BEACHCOMBERS

      3 BR / 2 BA / Sleeps 8 | Quick view

      Details

      Beachcombers is a spacious 3 bedroom/2 bath home with all of the "Old Florida Charm" you could ask for. Situated on Spring Avenue, just a couple of blocks to the Gulf of Mexico on Anna Maria's beautiful north end! Easy walking distance to many shops, restaurants, the Anna Maria City Pier and a short block to the free …
      • 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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      $250

      5 BR / 3 BA / Sleeps 12

      1 / 22

      $250

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      Tortuga Bay

      5 BR / 3 BA / Sleeps 12 | Quick view

      Details

      Tortuga Bay 9405 Gulf Dr. Anna Maria, FL 34216 This one is extraordinary! Tortuga Bay is a completely renovated, ground level, 5 bedroom property that has one of the most outstanding tropical pools on the island- featuring a theme-park style water-slide! Located in the prestigious city of Anna Maria, it is the…
      • Heated Pool
      • High Speed Internet
      • Patio
      • Television
      • DVD Player
      • Suitable for children - ask
      • Suitable for the elderly - ask

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      $200

      3 BR / 2 BA / Sleeps 6

      1 Reviews

      $200

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      Limelight

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

      Details

      Reviews

      (1)

      Limelight 771 Jacaranda Rd. Anna Maria, Fl. 34216 Limelight is a gorgeous newly renovated home, inside and out, located on the prestigious North End of Anna Maria Island. Only a brisk 3 minute walk away from the sandy white beaches, this home offers everything you are looking for in an Island vacation home. …
        • Suitable for children - ask
        • Suitable for the elderly - ask

        Details

        Reviews

        (1)

        Perfect vacation spot

        Left on Jan 11, 2015 for a stay in January 2015

        We loved the location and the house was beautiful and well equipped. It was a perfect place for us to vacation with our three adult children. The kitchen was top notch with beautiful appliances. They also supplied beach towels and towels and all the things necessary for an afternoon on the beach...beach chairs,coolers, umbrella. A big plus were the bikes that were available for us to use. We …

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        $171

        2 BR / 2 BA / Sleeps 4

        4 Reviews

        $171

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        Simpatico: 2BR Pet-Friendly Canal Home with Kayaks

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

        Details

        Reviews

        (4)

        With its luscious landscaping, eclectic look and colorful Key-West style, Simpatico could be right out of Coastal Living Magazine. This bungalow is perfect for the ideal secluded island vacation! Located on the north end of Anna Maria Island, this canal home, with a boat dock and kayaks, is just a short stroll to the …
        • Waterfront
        • Wireless Internet
        • Washing Machine
        • Clothes Dryer
        • Outdoor Dining Area
        • Suitable for children - over five
        • Suitable for the elderly

        Details

        Reviews

        (4)

        A relaxing, tropical paradise...

        Left on Apr 07, 2014 for a stay in March 2014

        This cottage is the perfect getaway spot for those who want a tropical experience. Located on a canal, this home was bright, clean, and cheery and packed with tropical foliage that made us feel like we had escaped to the tropics. There is a great entertaining area and backyard which our friends loved! Coastal Cottages were terrific and extremely responsive when we called with questions during …

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        $300

        5 BR / 3 BA / Sleeps 10

        1 / 26

        $300

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        Whitecaps

        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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        $258

        3 BR / 2 BA / Sleeps 6

        1 / 25

        $258

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        White Shell

        3 BR / 2 BA / Sleeps 6 | Quick view

        Details

        Gaze out of your living room to the calming serenity of the canal as you sip on your favorite beverage at this comfortable and spacious home located in the prestigious north end of the island. This beautiful 3 bedroom 2 bath tastefully decorated home is invitingly awaiting your arrival for the vacation of a lifetime…
        • Shared outdoor pool (unheated)
        • Internet Access
        • A/C or climate control
        • Balcony or terrace
        • Fitness Room
        • Suitable for children - ask
        • Suitable for the elderly - ask

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        $200

        3 BR / 2 BA / Sleeps 10

        1 / 14

        $200

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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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        $200

        3 BR / 2 BA / Sleeps 6

        1 / 12

        $200

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        A Snails Place

        3 BR / 2 BA / Sleeps 6 | Quick view

        Details

        A Snails Place 302 Spring Avenue Anna Maria, Fl. 34216 This beautifully decorated 3 bedroom, 2 bath ground level home is just a short walk to the Gulf of Mexico. With it's convenient location on Spring Avenue you are walking distance to historic Pine Avenue! This adorable cottage offers a splash pool (not heated…
        • Outdoor Pool
        • Internet Access
        • Dishwasher
        • Suitable for children - ask
        • Suitable for the elderly - ask

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        $209

        4 BR / 3 BA / Sleeps 10

        1 / 17

        $209

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        Sundown North

        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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        $253

        3 BR / 2 BA / Sleeps 8

        1 / 33

        $253

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        HURRICANE HOUSE

        3 BR / 2 BA / Sleeps 8 | Quick view

        Details

        Beautifully redone 3 bedroom/2.5 bath home! Ceramic tile throughout, and brand new open kitchen area with breakfast bar. Beautiful large caged pool area with huge covered patio! Only a block to the beach, the Sandbar Restaurant, Ginny and Jane E's, Rudy's Subs, Feeling Swell and more. Just a few steps away from …
        • 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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        $156

        2 BR / 1 BA / Sleeps 6

        9 Reviews

        $156

        Inquire

        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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        $221

        4 BR / 2 BA / Sleeps 6

        1 / 24

        $221

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        Maple by the Sea

        4 BR / 2 BA / Sleeps 6 | Quick view

        Details

        Located on one of the prettiest streets in the village of Anna Maria, this lovely 4 bedroom, 2 and a half bath home is just 7 houses away from the beach. The quiet, tree-lined street evokes memories of Florida Gulf Coast islands in days gone by, with a shaded path providing access to the island's fabulous white-sand …
        • Internet Access
        • A/C or climate control
        • Balcony or terrace
        • Fitness Room
        • Parking
        • Suitable for children - ask
        • Suitable for the elderly - ask

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        $209

        4 BR / 3 BA / Sleeps 8

        1 / 19

        $209

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        Casa Muratti

        4 BR / 3 BA / Sleeps 8 | Quick view

        Details

        Casa Muratti 210 Palmetto Avenue Anna Maria Fl. 34216 This is an exceptional 4 bedroom 3.5 bath Mediterranean style home just a short walk to the Gulf of Mexico. With its modern decor and bright open floor plan this home is perfect for your vacation getaway! There is a private heated pool and a large covered patio …
        • Outdoor Pool
        • Internet Access
        • Dishwasher
        • Suitable for children - ask
        • Suitable for the elderly - ask

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        $450

        5 BR / 4 BA / Sleeps 10

        1 / 26

        $450

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        The Big Yellow House

        5 BR / 4 BA / Sleeps 10 | Quick view

        Details

        The Big Yellow House on Pine 104 Pine Avenue Anna Maria Fl. 34216 This home is one of a handful of very select rental properties on the island- direct Gulf front with a private heated pool! It has all the perfect ingredients for a wonderful vacation. Enjoy your front row seat to spectacular sunsets from this …
        • Outdoor Pool
        • Internet Access
        • Suitable for children - ask
        • Suitable for the elderly - ask

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        $100

        1 BR / 1 BA / Sleeps 2

        1 / 24

        $100

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        Flamingo House: 1BR Elderly-Friendly Steps From Beach

        1 BR / 1 BA / Sleeps 2 | Quick view

        Details

        Enjoy your vacation in this charming, one-bedroom, one-bath original house just six houses away from the white sand beaches of Anna Maria Island and sparkling waters of the Gulf of Mexico. Flamingo House is perfect for anyone who needs a quick weekend getaway or an extended stay! Located in Anna Maria on the west …
        • Wireless Internet
        • A/C or climate control
        • Porch
        • Parking
        • Books
        • Suitable for the elderly

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        $190

        3 BR / 2 BA / Sleeps 6

        1 / 14

        $190

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        Dolphin Dreams

        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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        $150

        2 BR / 2 BA / Sleeps 8

        1 / 8

        $150

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        Copacabana

        2 BR / 2 BA / Sleeps 8 | Quick view

        Details

        Copacabana is a 2 bedroom, 2 bath private canal front home with a pool; with tile floors throughout and a designer's stylish touch, you will feel you have found your home away from home! Copacabana will accommodate 6-8 people and offers a separate family room with a large flat screen TV that is great for the kids. …
        • Waterfront
        • Ocean or water views
        • Internet Access
        • Washing Machine
        • Clothes Dryer
        • Pet friendly
        • Suitable for children
        • Suitable for the elderly

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        $283

        3 BR / 2 BA / Sleeps 6

        2 Reviews

        $283

        Inquire

        CARIBBEAN SOUL

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

        Details

        Reviews

        (2)

        Beautifully remodeled 3 bedroom/2.5 bath home with luxury amenities on the North End of Anna Maria, just 4 houses to Bean Point, one of the quietest beaches on the island, and 2 blocks to the famous Rod & Reel Pier! Private Backyard with Heated Pool, and an open floor plan with vaulted ceilings! Sleeps up to 6. …
        • Internet Access
        • Washing Machine
        • Clothes Dryer
        • Outdoor Dining Area
        • A/C or climate control
        • Suitable for children
        • Suitable for the elderly

        Details

        Reviews

        (2)

        Fabulous getaway

        Left on Sep 28, 2013 for a stay in April 2013

        This was my first trip to anna Marie Island. The area and weather is gorgeous in april. The accommodations are amazing with everything you can possible want or need provided. I would love to make this an annual event.

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        $150

        2 BR / 1 BA / Sleeps 6

        6 Reviews

        $150

        Book

        Coral Cottage 2 BR in Anna Maria 1 Blk to Beach

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

        Details

        Reviews

        (6)

        1940’s Classic beach cottage located at 9901 Gulf Drive Anna Maria, recently renovated, two bedrooms, one bath, with an eclectic, artistic decorating style that will bring a smile to your face and make your stay here a memorable experience. Located only five houses from the white, sugar sand beaches of the Gulf of …
        • Internet Access
        • Washing Machine
        • Clothes Dryer
        • A/C or climate control
        • Central heating
        • Pet friendly
        • Suitable for children
        • Suitable for the elderly - ask
        • Wheelchair accessible - ask

        Details

        Reviews

        (6)

        Location Location Seriously Location!!!!

        Left on Dec 09, 2013 for a stay in December 2013

        TheLocation of this dog friendly cottage is awesome. It is right on Gulf drive, only a block from the beach (gulf side) and a few blocks from Tampa Bay. It is also very short walking distance from any local businesses you might need or want to visit (coffee shop, bars, restaurants, general store, sub shop, etc). The price was very reasonable. We were impressed with this size of the home & …

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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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        $225

        4 BR / 2 BA / Sleeps 10

        1 / 15

        $225

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        Whispering Whale Retreat

        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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        $229

        3 BR / 2 BA / Sleeps 6

        1 / 17

        $229

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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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        $179

        2 BR / 1 BA / Sleeps 4

        1 / 14

        $179

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        Moondance

        2 BR / 1 BA / Sleeps 4 | Quick view

        Details

        Moondance 206 Spring Lane Anna Maria, Fl. 34216 If you are looking for a unique property you have found it! This property sits right out on the beach and has a private balcony from the property to the beach. Nestled in the heart of Anna Maria, Moondance offers quaint privacy but is only a very short walk over to …
        • Internet Access
        • Dishwasher
        • Suitable for children - ask
        • Suitable for the elderly - ask

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        $189

        3 BR / 2 BA / Sleeps 7

        8 Reviews

        $189

        Inquire

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

        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
        • Patio
        • 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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        $715

        4 BR / 4 BA / Sleeps 14

        5 Reviews

        $715

        Inquire

        Golden Dolphin

        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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        $133

        1 BR / 1 BA / Sleeps 2

        1 Reviews

        $133

        Inquire

        SUMMER BREEZE

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

        Details

        Reviews

        (1)

        Newly Remodeled 1 Bedroom/1 Bath Cottage in a serene north end location. 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 from the dock or choose to bring your own vessel to explore …
        • Ocean or water views
        • Internet Access
        • Washing Machine
        • Clothes Dryer
        • Outdoor Dining Area
        • Pet friendly
        • Suitable for children
        • Suitable for the elderly

        Details

        Reviews

        (1)

        getting away for a week

        Left on Nov 14, 2013 for a stay in October 2013

        We stayed on anna Maria Island for a week & it was tremendous. Not just the Island itself. While anna Maria Island has kept itself modern in many ways, its also kept itself "accessible". Thats not easy in the age of 12 story condos & "no beach access" unless you are rich.

        But the Island itself was only part of our tremendous week. Our stay at Summer Breeze, a dated duplex with what was once …

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