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$250

5 BR / 3 BA / Sleeps 12

1 Reviews

$250

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Tortuga Bay

5 BR / 3 BA / Sleeps 12 | Quick view
“ Very Good ” 1 Reviews

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Reviews

(1)

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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Reviews

(1)

Amazing week in paradise

Left on Apr 02, 2015 for a stay in March 2015

The house was beautiful, spotless, and comfortable. The pool area was amazing and the walk to the beach was seriously 2 minutes tops. We like to stay beach front so if the beach wasn't too far for me it shouldn't be to far for anyone. The negative side - it was on the main road - the traffic never stopped - a little nerve racking with the kids. But the front yard - like a giant parking lot - …

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$425

4 BR / 3 BA / Sleeps 8

6 Reviews

$425

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La Plage 03

4 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 6 Reviews

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Reviews

(6)

L’Plage Condominium #3 located at 6420 Gulf Drive in the preferred northern end of Holmes Beach is a spectacular four bedroom, three bath Gulf front unit with a glorious beachside swimming pool and spa. There is even a BBQ area onsite for your use! L’Plage Condominium features a security gated entry, elevator and …
  • 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

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Reviews

(6)

Great Place

Left on Apr 08, 2009 for a stay in March 2009

We definitely enjoyed our stay! Out trip was a birthday celebration among friends. So having the 4br/3baths for 8 worked out wonderfully. The condo is beautiful and the location is great.

Our only problem was figuring out the garage openers and then the code for the gate at the pool. We had 3 garage openers and none worked. We only parked once in the garage after somebody got out in the …

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$150

4 BR / 4 BA / Sleeps 8

Sunbow Bay 1B - Anna Maria Island vacation rentals
1 / 21

$150

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Sunbow Bay 1B

4 BR / 4 BA / Sleeps 8 | Quick view

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Sunbow Bay Condominium 1B located at 3701 East Bay Drive in Holmes Beach has everything you could need or want for a memorable vacation. Conveniently close to shopping and restaurants yet out of the way and quiet. Sunbow Bay offers two heated pools, tennis courts, undercover parking and every conceivable amenity to …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$225

4 BR / 2 BA / Sleeps 12

4 Reviews

$225

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Dolphin Dance, Both units

4 BR / 2 BA / Sleeps 12 | Quick view
“ Very Good ” 4 Reviews

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Reviews

(4)

The Dolphin Dance, located at 803 and 805 Gulf Drive South is an impressive duplex with unobstructed, panoramic views of the Gulf of Mexico. Each side has two bedrooms and one and one half baths. Each sleeps six with a queen size bed, two double beds and a sofa bed. There is a shared washer and dryer onsite for your …
  • Ocean or water views
  • Internet Access
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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Reviews

(4)

Disappointed

Left on Apr 09, 2009 for a stay in March 2009

We really like the home, but when we arrived at 4:00 the cleaning personnel were still there and continued to clean until 4:45. Also, the internet on the south side didn't work, a blind was torn down, and the bathroom door wouldn't shut completely. Otherwise, the view is beautiful.

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$496

5 BR / 4 BA / Sleeps 10

7 Reviews

$496

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Seahorse Cove: 5BR Amazing Pool Home with Dock

5 BR / 4 BA / Sleeps 10 | Quick view
“ Excellent ” 7 Reviews

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Reviews

(7)

Located on the north end of Anna Maria Island in the city of Anna Maria, this family-friendly vacation rental was built for rest and relaxation. Beginning with the lush landscaping that meets you at the front door, all the way through to the putting green, kayak launch and boat dock, this house has high standards. A …
  • Waterfront
  • Sauna
  • Spa/Whirlpool
  • Wireless Internet
  • Fireplace
  • Suitable for children - over five
  • Suitable for the elderly - ask

Details

Reviews

(7)

Great house, but Coastal Cottages could use lessons in Customer

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

The Seahorse Cove home is outstanding - the furnishings are gorgeous and top of the line. The pool is just as exotic as it looks in the photos. I have nothing but rave reviews about the home itself. What mars my opinion of this property was the treatment we received from Coastal Cottages (the company that maintains the home).

When we arrived on Saturday (which is a typical arrival day), the …

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$309

5 BR / 3 BA / Sleeps 10

1 Reviews

$309

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CORAL CASTLE

5 BR / 3 BA / Sleeps 10 | Quick view
“ Excellent ” 1 Reviews

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Reviews

(1)

Beautiful, Brand New, 5 bedroom/3.5 bath Waterfront home with Heated Pool, Hot Tub, Dock, and just over a block to the beach! Covered Patio by pool area and peeks of the Gulf and Bay from the top patios. Great location in a quiet neighborhood, a few steps to the Trolley Stop, and a short walk to the Public Beach and…
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

awesome

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

the coral castle was a great place for our vacation. It was very convenient to everything. What was really nice, was that when we went fishing, the captain picked us up in our back yard.The pool was amazing and perfect for kids of all ages. The home had nearly everything we needed and was set up for a large group to be together yet have some space.The back patio was really nice too although I do …

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$160

4 BR / 2 BA / Sleeps 8

1 / 18

$160

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Hawaiian Hideaway

4 BR / 2 BA / Sleeps 8 | Quick view

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Hawaiian Hideaway 206 81st Street Unit A Holmes Beach, Fl 34217 Hawaiian Hideaway is a brand new ground level private duplex! A true gem of a home with a private heated pool and tropical landscaping throughout the backyard area for privacy. Centrally located, this property is close to it all - beaches, shops, …
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $400

    6 BR / 4 BA / Sleeps 16

    1 / 29

    $400

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    Conch House

    6 BR / 4 BA / Sleeps 16 | Quick view

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    Conch House 307 B 66th St. Holmes Beach, Fl. 34217 Conch House is a brand new construction, luxury island home with 6 bedrooms and 4.5 bathrooms. The pool area is an oasis of luxury, including a 6' water-slide, a unique enclosed "grotto" spa, lush tropical landscaping, a pool side bar with TV under the large …
    • Private Pool
    • High Speed Internet
    • Patio
    • Television
    • DVD Player
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $400

    8 BR / 5 BA / Sleeps 20

    1 Reviews

    $400

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    Tropical Oasis

    8 BR / 5 BA / Sleeps 20 | Quick view
    “ Poor ” 1 Reviews

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    Reviews

    (1)

    Tropical Oasis 204 72nd St. Holmes Beach, Fl. 34217 Tropical Oasis is the pinnacle of Anna Maria Island luxury vacationing. This palatial 8 bedroom, 5.5 bathroom is something out of your dreams. A home that truly has it all with beautiful hardwood floors, crown moldings, fine fixtures, granite counter and so …
    • Private Pool
    • High Speed Internet
    • Patio
    • Television
    • DVD Player
    • Suitable for children - ask
    • Suitable for the elderly - ask

    Details

    Reviews

    (1)

    Good Home Terrible Customer Service

    Left on Mar 13, 2015 for a stay in March 2015

    The home itself is beautiful. Wonderful and comfortable beds, great pool, and close to beach. The Anna Maria Vacation Rental group is terrible. We have rented with them twice so far and both times their customer service is awful. The first time they promised us a rental which was not completely built when we were ready to come. They ended up putting us up in a different home which also was …

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    $468

    4 BR / 4 BA / Sleeps 16

    1 / 22

    $468

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    Four Beach Lovers all units

    4 BR / 4 BA / Sleeps 16 | Quick view

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    Welcome to the Four Beach Lovers (Formerly Dawg Daze). Located at 2908 Avenue E in Holmes Beach, this gulf front tropical paradise features four well-appointed and comfortable one bedroom units. Each of the four units is fully equipped and tastefully furnished. All four units feature a private patio area and a …
    • 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

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    $209

    4 BR / 4 BA / Sleeps 10

    1 Reviews

    $209

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    Villa Milano

    4 BR / 4 BA / Sleeps 10 | Quick view
    “ Average ” 1 Reviews

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    Reviews

    (1)

    Villa Milano 4006 5th Avenue Holmes Beach, FL 34217 This casually elegant Mediterranean style 4 bedroom, 4 full bathroom vacation residence has views of the Gulf waters and its own heated swimming pool set in a gated, private garden area. Just a two minute stroll from the beach, this Mediterranean villa is topped …
    • Outdoor Pool
    • Internet Access
    • Dishwasher
    • Suitable for children - ask
    • Suitable for the elderly - ask

    Details

    Reviews

    (1)

    A few things missing.

    Left on Aug 18, 2014 for a stay in August 2014

    At first glance the place seems great. Location to beach, shopping, and restaurants is ideal.

    Once your there awhile you start to notice a few things. Lots of water damage on west walls of building. Rot around windows and doors. Water stains on ceilings and walls.

    There is no common bathroom in the house. You must go though a bedroom to use restroom.

    When you go to the beach and return to…

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    $290

    5 BR / 3 BA / Sleeps 12

    6 Reviews

    $290

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    Gorgeous views,spectacular home!

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

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    Reviews

    (6)

    WELCOME TO ALL DECKED OUT! Whether getting away for a family vacation, with a group of friends, for a wedding or any other occasion, our gorgeous 5 Bedroom home offers everything you could want for a relaxing holiday on Anna Maria Island.... with incredible views of the Bay! Sit by the tropical courtyard garden, …
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly - ask

    Details

    Reviews

    (6)

    A week of Bliss!

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

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

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    $843

    4 BR / 4 BA / Sleeps 14

    5 Reviews

    $843

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    Golden Dolphin

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

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    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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    $421

    6 BR / 5 BA / Sleeps 16

    1 / 29

    $421

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    Gulfside Oasis

    6 BR / 5 BA / Sleeps 16 | Quick view

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    Gulfside Oasis 204 66th St. Holmes Beach, Fl. 34217 This is it- the pinnacle of Anna Maria Island luxury! Gulfside Oasis is a brand new luxury home that combines comfort, class and convenience. Spacious, with 6 bedrooms and 5 full bathrooms, this property is the perfect get-away for larger parties or multiple …
    • Private Pool
    • High Speed Internet
    • Patio
    • Television
    • DVD Player
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $235

    4 BR / 4 BA / Sleeps 8

    32 Reviews

    $235

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    Serenity

    4 BR / 4 BA / Sleeps 8 | Quick view
    “ Excellent ” 32 Reviews

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    Reviews

    (32)

    The Serenity is a custom built four bedroom, four bath pool home located at 2914 Avenue E in Holmes Beach. Just one house from the beach, the Serenity has sweeping views of the Gulf of Mexico from the master bedroom suite. Additional features include tile and natural wood floors throughout, individually hand painted …
    • Ocean or water views
    • Shared outdoor pool (unheated)
    • Internet Access
    • Grill
    • Pet friendly
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (32)

    Great Vacation - Great Location!

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

    We rented this home for a family vacation with all 5 of our grown children and grandchildren. Steps from the beach and walking distance to Publix, Walgreen's, subway and Shell's resturant! We had a great time! Would definately do it again if we can get everyone together!

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    $272

    4 BR / 3 BA / Sleeps 12

    1 Reviews

    $272

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    5 Bedroom w/ Lagoon pool, hot tub & golf cart

    4 BR / 3 BA / Sleeps 12 | Quick view
    “ Very Good ” 1 Reviews

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    Reviews

    (1)

    Anna Maria Island offers a family oriented vacation destination, laid back feel ...very relaxing. The island's beauty, world famous white beaches and friendly atmosphere will make you want to come back. The four bedroom home with a Golf Cart to bop around the island. The home is furnished with a king bed, in the …
    • Hot Tub/Jacuzzi
    • Wireless Internet
    • Housekeeping Optional
    • Washing Machine
    • Clothes Dryer
    • Pet friendly
    • Smoking allowed - ask
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible

    Details

    Reviews

    (1)

    Great vacation home with pool!

    Left on Oct 02, 2014 for a stay in September 2014

    We enjoyed our stay at Casa Laguna. Great location just a few blocks from the beach and the option to use the golf cart was a nice perk for getting there easily. The pool and spa was the most perfect, private space to enjoy warm afternoons and evenings. I would recommend this house to friends.

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    $350

    6 BR / 4 BA / Sleeps 14

    1 / 30

    $350

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    Sands of Time

    6 BR / 4 BA / Sleeps 14 | Quick view

    Details

    Sands of Time 6908 Holmes Blvd. Holmes Beach, Fl. 34217 Sands of Time is a brand new luxury island tropical home with 6 bedrooms, 4.5 bathrooms and is only a short 2-3 minute stroll to the Gulf beach. The heated pool features a deluxe spa and an over-sized lanai next to the pool features a dining table, flat …
    • Heated Pool
    • High Speed Internet
    • Patio
    • Television
    • DVD Player
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $360

    5 BR / 3 BA / Sleeps 16

    1 / 24

    $360

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    Willow Beach House

    5 BR / 3 BA / Sleeps 16 | Quick view

    Details

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

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      $250

      4 BR / 2 BA / Sleeps 9

      1 / 21

      $250

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      Away To Play

      4 BR / 2 BA / Sleeps 9 | Quick view

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      Away to Play 117 White Avenue Holmes Beach Fl. 34217 This grand Victorian style Island home is luxury at its best! A newly constructed 4 bedroom, 2.5 bath elevated home with a private heated pool is surrounded by tropical landscaping. You will find Away to Play is a very short walk to the Gulf of Mexico - where …
      • Outdoor Pool
      • Internet Access
      • Dishwasher
      • Suitable for children - ask
      • Suitable for the elderly - ask

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      $270

      4 BR / 4 BA / Sleeps 10

      1 Reviews

      $270

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      Bay Delight both units

      4 BR / 4 BA / Sleeps 10 | Quick view
      “ Average ” 1 Reviews

      Details

      Reviews

      (1)

      The Bay Delight is just that; a delight! This bay side four bedroom, four bath duplex, located at 2500 Avenue B in Bradenton Beach offers every conceivable amenity to make your stay here a pleasant and comfortable one. Each unit offers full size washer and dryer, microwave and dishwasher. Shopping and restaurants …
      • Ocean or water views
      • Internet Access
      • Grill
      • Pet friendly - ask
      • Smoking allowed - ask
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      Details

      Reviews

      (1)

      Beautiful Condo

      Left on Feb 23, 2009 for a stay in June 2008

      The building is conveniently located to the beach and bay. The view of the bay from the top unit is spectacular for sunrises. Each unit is spacious, nicely furnished and fully equipped. The porch is a bonus. I have stayed here several times in the past and this condo quickly became my favorite spot on the island.
      The last two visits we had problems with the cleanliness of the units. In January of…

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      $317

      4 BR / 4 BA / Sleeps 10

      1 / 26

      $317

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      BEACH BOUND

      4 BR / 4 BA / Sleeps 10 | Quick view

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      Brand New Construction! Spacious Ground Level 4 Bedroom/4 Bath Home with One Car Garage, Heated Pool, and Hot Tub. Featuring Granite Countertops, Stainless Steel Appliances, and Flat Screens throughout. Great location in a quiet neighborhood, just a block to the beach, and close to the Trolley Stop. With 4 Bedrooms …
      • Hot Tub/Jacuzzi
      • Internet Access
      • Washing Machine
      • Clothes Dryer
      • Outdoor Dining Area
      • Suitable for children
      • Suitable for the elderly

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      $214

      4 BR / 3 BA / Sleeps 8

      1 / 17

      $214

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      Sundown South

      4 BR / 3 BA / Sleeps 8 | Quick view

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      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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      $471

      4 BR / 3 BA / Sleeps 10

      26 Reviews

      $471

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      Honeyfish, stunning views across Bimimi Bay!

      4 BR / 3 BA / Sleeps 10 | Quick view
      “ Excellent ” 26 Reviews

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      Reviews

      (26)

      Honeyfish is a fabulous, single storey vacation rental from Pineapplefish. Its location, on the edge of Bimini Bay, its nautically themed complete with boating artefacts, makes Honeyfish a water lover's dream luxury home on Anna Maria Island. Honeyfish is surrounded by the water and is perfect for visitors who …
        • Suitable for children
        • Suitable for the elderly
        • Wheelchair accessible

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        Reviews

        (26)

        Relaxing and friendly

        Left on Nov 28, 2009 for a stay in February 2009

        Anna Maria is such a beautiful island, the beaches are fantastic, the people so friendly, and the home we stayed in - Honeyfish, one of the Pineapplefish Villas - was fantastic. Brilliant decor, great location (especially if you like boating), and really great service from the owners and staff.

        Next time we're going to book Limefish - the pictures on the Pineapplefish website look gorgeous!

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        $535

        8 BR / 6 BA / Sleeps 19

        1 Reviews

        $535

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        Summer House

        8 BR / 6 BA / Sleeps 19 | Quick view
        “ Very Good ” 1 Reviews

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        Reviews

        (1)

        Summer House 211 54th St Holmes Beach, Fl 34217 Summer House is a brand new 8 bedroom and 6 bathroom rental home just completed and rental ready! The rental home has so many fun options for everyone- close to the beach, Gulf and Bay water views, table games, water slide, spa, roof top deck with hot tub (coming soon…
        • Heated Pool
        • High Speed Internet
        • Patio
        • Television
        • DVD Player
        • Suitable for children - ask
        • Suitable for the elderly - ask

        Details

        Reviews

        (1)

        Great for laid back vacation - Has it all

        Left on Dec 22, 2014 for a stay in December 2014

        Great house with heated pool, ping pong, pool table, hot tubs, etc.

        We had 9 people and plenty to spare.

        The kitchen is big, with plenty of dishes and bowls.

        The eating table can seat 12, which is one of the main reason we picked this property, as we only eat at the house, and we ate like kings.

        It is only 2 minutes to the beach, and a nice beach at that.

        I recommend it.

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        $300

        4 BR / 5 BA / Sleeps 8

        7 Reviews

        $300

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        4 bed luxury upscale executive waterfront home

        4 BR / 5 BA / Sleeps 8 | Quick view
        “ Excellent ” 7 Reviews

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        Reviews

        (7)

        Upscale luxury executive four bedroom waterfront home with private pool dock and elevator. Stylishly furnished and dressed, modern build 2006 - this is our family second home - and is home from home available to you. This exclusive executive property is in the heart of lovely Anna Maria Island; stroll to the …
        • Waterfront
        • Ocean or water views
        • Hot Tub/Jacuzzi
        • Internet Access
        • Washing Machine
        • Suitable for children
        • Suitable for the elderly - elevator access
        • Wheelchair accessible

        Details

        Reviews

        (7)

        Absolutely Wonderful!

        Left on Mar 16, 2011 for a stay in March 2011

        This house was absolutely perfect for us on our first trip to Anna Maria. We had a family of three (2 adults, 1 teen) and a family of four (2 adults, 1 teen, 1 child) stay at this wonderful home and it was a great setup! Each couple had their own master suite and the kids had their bedrooms. The kitchen and family room were large so we could hang out together there. The kids enjoyed the pool …

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        $350

        6 BR / 4 BA / Sleeps 15

        1 / 35

        $350

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        Pearl Beach

        6 BR / 4 BA / Sleeps 15 | Quick view

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        Pearl Beach 6906 Holmes Blvd. Holmes Beach, Fl. 34217 Pearl Beach is a brand new luxury Island home that features 6 bedrooms and 4.5 bathrooms and exudes luxury with its deluxe furniture, coastal decorations, gourmet kitchen and private heated pool with spa and waterslide! Ideal for larger gatherings, this home …
        • Heated Pool
        • High Speed Internet
        • Patio
        • Television
        • DVD Player
        • Suitable for children - ask
        • Suitable for the elderly - ask

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        $300

        5 BR / 4 BA / Sleeps 12

        2 Reviews

        $300

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        Coastal Winds

        5 BR / 4 BA / Sleeps 12 | Quick view
        “ Excellent ” 2 Reviews

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        Reviews

        (2)

        Coastal Winds 303 Church St. Bradenton Beach, Fl 34217 Coastal Winds is a brand new 5 bedroom + bonus room, 4.5 bathroom private rental home that is currently under construction with completion in early May 2014. Reservations excepted beginning June 1st, 2014. This luxury home offers sweeping Gulf and Bay water …
          • Suitable for children - ask
          • Suitable for the elderly - ask

          Details

          Reviews

          (2)

          Beautiful Home

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

          My family, consisting of four couples and one single, stayed in this home during October 2014. We all were very pleased with the accommodations. Every room was immaculately clean and lovely. A large screen TV in every bedroom, both living rooms, and outside by the pool. Two master bedrooms had large en suite bathrooms. Another bedroom has a bathroom a few steps down the hall and the final …

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          $250

          4 BR / 3 BA / Sleeps 10

          1 / 26

          $250

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          Blue Heron

          4 BR / 3 BA / Sleeps 10 | Quick view

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          Blue Heron 309B 65th St. Holmes Beach, Fl. 34217 A cute and fun island vacation retreat! It is newer construction with 4 bedroom, 3.5 bathroom and a private heated pool! It has everything you want in an tropical island vacation rental property- lush landscaping, flat screen HD TV's throughout, hardwood floors, …
          • Heated Pool
          • High Speed Internet
          • Patio
          • Television
          • DVD Player
          • Suitable for children - ask
          • Suitable for the elderly - ask

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          $329

          4 BR / 3 BA / Sleeps 10

          1 / 26

          $329

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          Avalon

          4 BR / 3 BA / Sleeps 10 | Quick view

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          Avalon 2803 Ave E Holmes Beach, Fl. 34217 Wow, if you have looked at the pictures what else is there to say! The views on this fantastic new luxury 4 bedroom, 3.5 bathroom are simply out-of-this-world! Avalon truly has it all- luxury from the word go. Fine travertine marble, custom hard wood, premium fixtures …
          • Private Pool
          • High Speed Internet
          • Patio
          • Television
          • DVD Player
          • Suitable for children - ask
          • Suitable for the elderly - ask

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          $230

          4 BR / 4 BA / Sleeps 8

          1 / 19

          $230

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          Riki Tiki

          4 BR / 4 BA / Sleeps 8 | Quick view

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          Riki Tiki 110 46th Street Holmes Beach, Fl 34217 Riki Tiki is a beautiful beach house that is only 3 houses away from the stunning Gulf of Mexico. Offering a fantastic location, private heated pool, lots of amenities including a gourmet and fully stocked kitchen and much more! The sleeping arrangements for Riki …
            • Suitable for children - ask
            • Suitable for the elderly - ask

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            $220

            5 BR / 3 BA / Sleeps 14

            15 Reviews

            $220

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            Captain Billy Fulford Home

            5 BR / 3 BA / Sleeps 14 | Quick view
            “ Excellent ” 15 Reviews

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            Reviews

            (15)

            The Captain Billy Fulford House is a rare five bedroom, three and one half bath home located at 4523 123rd Street West in the Historic Village of Cortez. This wonderful, old home features a 20' x 40' private, heated pool. Built in 1907, this 105 year old home is a wonderful piece of living history. Deep sea and inland…
            • Ocean or water views
            • Shared outdoor pool (unheated)
            • Internet Access
            • Grill
            • Pet friendly
            • Smoking allowed - ask
            • Suitable for children - ask
            • Suitable for the elderly - ask
            • Wheelchair accessible - ask

            Details

            Reviews

            (15)

            Great family experience

            Left on Feb 23, 2009 for a stay in July 2008

            My wife found this home several years ago while searching for historic homes to rent in the Anna Maria Island area. We had a family of 6 (now 7) at the time and we needed the space that the home provided. We were also happy that the home had a pool and was close to Holmes and Coquina beaches. It is within walking distance to many water sport activities, a small grocery store, a restaurant and the…

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            $250

            4 BR / 3 BA / Sleeps 10

            1 / 19

            $250

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            Island Retreat

            4 BR / 3 BA / Sleeps 10 | Quick view

            Details

            Island Retreat 4805 2nd Avenue Holmes Beach, FL 34217 Key West meets Anna Maria Island in a dream vacation home. Island Retreat combines the best of both worlds, oozing a traditional south Florida style outside, with shaded balconies and intricate wooden architecture, with unrivalled, modern luxury on the inside. …
            • Heated Pool
            • High Speed Internet
            • Patio
            • Television
            • DVD Player
            • Suitable for children - ask
            • Suitable for the elderly - ask

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            $300

            5 BR / 3 BA / Sleeps 12

            1 / 22

            $300

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            Mojito Splash

            5 BR / 3 BA / Sleeps 12 | Quick view

            Details

            Mojito Splash 304 65th St. Holmes Beach, Fl. 34217 This beautiful 5 bedroom, 3.5 bathroom Island style home is perfect for all your vacation needs. It is only a short 2-3 minute walk to the white sand beaches of the Gulf of Mexico. It also is a very short walk to the free trolley stop which can take you from one …
            • Private Pool
            • High Speed Internet
            • Patio
            • Television
            • DVD Player
            • Suitable for children - ask
            • Suitable for the elderly - ask

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            $600

            6 BR / 5 BA / Sleeps 14

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            $600

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            Hunters Point

            6 BR / 5 BA / Sleeps 14 | Quick view

            Details

            Hunters Point 4510 125th St. Cortez, Fl. 34215 Hunters Point is a unique and special vacation "luxury compound" that provides all the exceptional amenities that a discriminating vacationer is looking for in a unique setting. This outstanding 6 bedroom, 5.5 bathroom property has an amazing 500+ feet of water …
              • Suitable for children - ask
              • Suitable for the elderly - ask

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              $350

              6 BR / 3 BA / Sleeps 12

              1 / 30

              $350

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              Beachbreeze

              6 BR / 3 BA / Sleeps 12 | Quick view

              Details

              Beachbreeze 130 50th St. Holmes Beach, Fl. 34217 Anna Maria Island is famous for its beaches. And rightly so, when one side of the island is basically just one long, seven-mile stretch of pure white sand it’s not surprising that people have started to notice. But while the island is never exactly wide, even at …
              • Heated Pool
              • High Speed Internet
              • Patio
              • Television
              • DVD Player
              • Suitable for children - ask
              • Suitable for the elderly - ask

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              $250

              4 BR / 3 BA / Sleeps 8

              1 / 26

              $250

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              Avenue E By The Sea

              4 BR / 3 BA / Sleeps 8 | Quick view

              Details

              Avenue E by the Sea 3105 Gulf Drive Holmes Beach, Fl 34217 Wow! Beautiful views of the sparkling Gulf waters can be seen from the living room, kitchen, large covered 2nd floor porch and the roof-top deck- unbelievable!. This luxury home has much more than just views, it offers many extras for your relaxing …
              • Private Pool
              • High Speed Internet
              • Patio
              • Television
              • DVD Player
              • Suitable for children - ask
              • Suitable for the elderly - ask

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              $300

              5 BR / 4 BA / Sleeps 12

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              Bayfront Paradise

              5 BR / 4 BA / Sleeps 12 | Quick view

              Details

              Bayfront Paradise 238 South Harbor Dr. Holmes Beach, Fl 34217 Bayfront Paradise is an absolutely stunning custom luxury home that is tucked away on a quiet residential street with the most amazing Bay views. As soon as you enter the property you are immediately immersed in the relaxing isle atmosphere of Anna Maria…
              • Heated Pool
              • High Speed Internet
              • Patio
              • Television
              • DVD Player
              • Suitable for children - ask
              • Suitable for the elderly - ask

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              $471

              6 BR / 4 BA / Sleeps 16

              1 Reviews

              $471

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              ABSOLUTE PARADISE

              6 BR / 4 BA / Sleeps 16 | Quick view
              “ Excellent ” 1 Reviews

              Details

              Reviews

              (1)

              Completely Updated, Designer furnished 6 bedroom/5 bath home with large privacy fenced yard, Heated Pool, Hot Tub, Ping Pong Table, and Boat Slip(across street, depth depends on tides)! Covered Tiki Bar by pool area. Kids game room in 6th bedroom with large flat screen TV, Wii, Playstation, and XBox360. Great location…
              • Ocean or water views
              • Hot Tub/Jacuzzi
              • Internet Access
              • Washing Machine
              • Clothes Dryer
              • Suitable for children
              • Suitable for the elderly

              Details

              Reviews

              (1)

              Perfect Getaway on the perfect island

              Left on Feb 03, 2014 for a stay in January 2014

              The house is beautiful, well furnished, big enough for a large group, has great views, and close to the beach. The island is perfect - beautiful beach, no high rises, people walking and biking, trolleys, and a ton of great little locally owned restaurants and beach front bars. I would go back!

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              $300

              5 BR / 4 BA / Sleeps 12

              1 / 29

              $300

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              Harbor Breeze

              5 BR / 4 BA / Sleeps 12 | Quick view

              Details

              Harbor Breeze 240 South Harbor Drive Holmes Beach, Fl. 34217 A spacious, newly constructed, home with 5 bedrooms and 4.5 bathrooms, Harbor Breeze will offer it all - deluxe private heated pool with hot tub - and the best part is that the pool overlooks the Bay with direct view of the Skyway Bridge! Harbor Breeze …
              • Heated Pool
              • High Speed Internet
              • Patio
              • Television
              • DVD Player
              • Suitable for children - ask
              • Suitable for the elderly - ask

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              $414

              5 BR / 3 BA / Sleeps 13

              12 Reviews

              $414

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              Valhalla Up and Down

              5 BR / 3 BA / Sleeps 13 | Quick view
              “ Excellent ” 12 Reviews

              Details

              Reviews

              (12)

              The Valhalla located at 3216 Gulf Drive in Holmes is a wonderful five bedroom, three bath Gulf front duplex on a secluded beach. While the Valhalla is tucked away in a quiet area, it is within walking distance to shopping and restaurants. The location is perfect!Each unit features a large covered deck that is a …
              • Waterfront
              • Ocean or water views
              • Internet Access
              • Pet friendly
              • Smoking allowed - ask
              • Suitable for children - ask
              • Suitable for the elderly - ask
              • Wheelchair accessible - ask

              Details

              Reviews

              (12)

              Wonderful Family Location

              Left on Mar 05, 2009 for a stay in July 2008

              Our extended family met here at the Valhalla. Accomodated 3 families plus a grandparent very comfortably. We used the uppper kitchen for family dinners and the lower kitchen for beach supplies, lots of waters, sodas, juices and snacks. Location is wonderful, units were clean and comfortable, low on a few kitchen supplies but not really a problem. The only think that I would mention is that …

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              $514

              6 BR / 4 BA / Sleeps 14

              3 Reviews

              $514

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              TWOPINACOLADAS

              6 BR / 4 BA / Sleeps 14 | Quick view
              “ Poor ” 3 Reviews

              Details

              Reviews

              (3)

              Welcome to the ultimate in Large Family luxury vacation Homes, with peeks of the Gulf of Mexico from the balconies. This Brand New, 6 bedroom/4.5 bath home with 10' ceilings, Granite countertops, and Stainless Appliances features a large privacy fenced yard, Tropical Heated Pool and Hot Tub, Swim Up Tiki, and covered…
              • Ocean or water views
              • Hot Tub/Jacuzzi
              • Internet Access
              • Washing Machine
              • Clothes Dryer
              • Pet friendly
              • Suitable for children
              • Suitable for the elderly

              Details

              Reviews

              (3)

              Poor up-keep, poor management, not worth the money!

              Left on Feb 03, 2014 for a stay in December 2013

              Our family rented this home for the week of Christmas and at first glance it was a lovely home. The problems began almost immediately. Dishwasher didn't work, so they sent a repairman out to fix and then replace it the next day which was terribly inconvenient. The ice machine in the refrigerator didn't work so we had to purchase ice everyday and keep it in coolers. Many of the lightbulbs …

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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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              $209

              4 BR / 3 BA / Sleeps 10

              1 Reviews

              $209

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              Bimini Bay

              4 BR / 3 BA / Sleeps 10 | Quick view
              “ Very Good ” 1 Reviews

              Details

              Reviews

              (1)

              Bimini Bay 4807 2nd Ave. Holmes Beach, Fl. 34217 Because you deserve the best: Bimini Bay is that stunning Island style 4 bedrooms, 3.5 baths, private luxury vacation home you have been dreaming of. Outfitted with beautiful and high end tropical furnishings and open living space, it is perfect for your family …
              • Heated Pool
              • High Speed Internet
              • Patio
              • Television
              • DVD Player
              • Suitable for children - ask
              • Suitable for the elderly - ask

              Details

              Reviews

              (1)

              Beautiful holiday rental

              Left on Jun 15, 2014 for a stay in May 2014

              We stayed at Bimini Bay on 2nd Avenue in mid May for 2 weeks. We were not disappointed.

              We were a party of 3 couples. The master suites with en-suites were delightful and the 3rd double room still had a great bathroom next door. All bedrooms were as described and the small lounge area upstairs was a bonus. We were very comfortable in this house. It's in a really great part of the Island, 3 …

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              $685

              9 BR / 6 BA / Sleeps 21

              1 / 59

              $685

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              The Blue Horizon

              9 BR / 6 BA / Sleeps 21 | Quick view

              Details

              The Blue Horizon 99 26th Street N. Bradenton Beach, Fl. 34217 9 bed luxury- Short stay fill in specials available for the fall! There is no more fantastic direct Gulf front luxury home than this. It simply has it all- newly constructed, exquisite 9 bedroom, 7.5 baths compound that will simply not disappoint. Two…
              • Private Pool
              • High Speed Internet
              • Patio
              • Television
              • DVD Player
              • 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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              $229

              4 BR / 3 BA / Sleeps 8

              2 Reviews

              $229

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              ENDLESS SUMMER

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

              Details

              Reviews

              (2)

              Beautiful, completely remodeled, ground level 4 bedroom/3 bath Home in a quiet neighborhood located just over a block to the beautiful white sand gulf beach. Close to shops and restaurants, and just a short block to the free trolley stop. Within an easy walk of Hurricane Hanks, A Moveable Feast,The Eat Here Restaurant…
              • Internet Access
              • Washing Machine
              • Clothes Dryer
              • Outdoor Dining Area
              • A/C or climate control
              • Suitable for children
              • Suitable for the elderly

              Details

              Reviews

              (2)

              Wow

              Left on Jun 20, 2014 for a stay in April 2014

              All I can say is that this house had the wow factor (for us), it was almost perfect.

              The layout of the house was great, it was fully fitted out and had everything we needed.

              The fenced off pool was great was we had small children, with outside space was really nice, especially having a lawn rather than concrete it allowed the children to play outside whilst we did other things - the almost …

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              $535

              8 BR / 6 BA / Sleeps 20

              1 / 40

              $535

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              Surf View

              8 BR / 6 BA / Sleeps 20 | Quick view

              Details

              Surf View 209 54th St Holmes Beach, Fl 34217 Surf View is a newly constructed custom luxury home that is now ready for rental! The home is lavish and bold- it offers everything you would expect out of a luxury home and more!! Enjoy the private heated pool, waterslide, spa, swim-up Tiki table, rooftop deck with …
                • Suitable for children - ask
                • Suitable for the elderly - ask

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                $514

                6 BR / 5 BA / Sleeps 14

                1 Reviews

                $514

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                CASADELSOL

                6 BR / 5 BA / Sleeps 14 | Quick view
                “ Excellent ” 1 Reviews

                Details

                Reviews

                (1)

                Welcome to the ultimate in Large Family luxury vacation Homes, with peeks of the Gulf of Mexico from the front balconies, and wide open intercoastal waterway views from the back of the home. This Brand New, 6 bedroom/5 bath home with Elevator features a large Tropical Heated Pool, Swim Up Table, and covered patio by …
                • Waterfront
                • Ocean or water views
                • Internet Access
                • Washing Machine
                • Clothes Dryer
                • Suitable for children
                • Suitable for the elderly

                Details

                Reviews

                (1)

                Awesome Vacation

                Left on Aug 15, 2013 for a stay in June 2013

                We are a family of 10 and had a wonderful time at Casadelsol. Plenty of room for all. The kids spend most of the time in the pool, kayaking, fishing, or walking over to the ocean and playing there. So much to do that no one got bored. Loved it!

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                $343

                4 BR / 3 BA / Sleeps 10

                1 / 40

                $343

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                LA HACIENDA

                4 BR / 3 BA / Sleeps 10 | Quick view

                Details

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

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                $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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