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$70

3 BR / 2 BA / Sleeps 6

The Stepping Stone - Anna Maria Island vacation rentals
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The Stepping Stone

3 BR / 2 BA / Sleeps 6 | Quick view

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"The Stepping Stone" is truly a stone's throw away from the beaches of Anna Maria Island just over the Anna Maria Bridge in Bradenton, Florida. Tucked away on a tree lined, quiet residential street, this spacious and well appointed three bedroom, two bath home offers the best of both worlds. Take advantage of the …
  • Internet Access
  • Satellite or cable TV
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$220

3 BR / 2 BA / Sleeps 7

4 Reviews

$220

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Hideaway

3 BR / 2 BA / Sleeps 7 | Quick view
“ Very Good ” 4 Reviews

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Reviews

(4)

The Hideaway, located at 5002 5th Avenue in Holmes Beach is a gulf front home which will take you back in time when living was easy. This wonderful home was built in the 1940’s and still has the same charm and ambience of days gone by. Magnolia wood walls and ceilings throughout the home give the feel of an old time…
  • Waterfront
  • 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

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Reviews

(4)

Classic Florida Beach House

Left on May 05, 2011 for a stay in April 2011

I grew up in Bradenton, and know anna Maria Island well. The Hideaway is a gem of a place from a era when most of the island consisted of single family homes, and not condos or monstrous beach pads. If you want a place right on the beach, that still has "old Florida charm", then this is the place.

I found the management company extremely responsive when we had a small problem with the phone …

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$125

3 BR / 2 BA / Sleeps 8

Egrets Landing - Anna Maria Island vacation rentals
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$125

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Egrets Landing

3 BR / 2 BA / Sleeps 8 | Quick view

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Egrets Landing 303 74th St. Unit A Holmes Beach, Fl. 34217 Egrets Landing is a brand new ground level construction with a private heated pool! Offering the best of all that Anna Maria Island has to offer with its central location, you are never too far from white sandy beaches, local cuisine, shops and the popular …
  • Heated Pool
  • High Speed Internet
  • Patio
  • Television
  • DVD Player
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$125

3 BR / 2 BA / Sleeps 6

Casa Blanca - Anna Maria Island vacation rentals
1 / 25

$125

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Casa Blanca

3 BR / 2 BA / Sleeps 6 | Quick view

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Spend your vacation just steps from our beautiful beaches and crystal-clear waters! Casa Blanca is in the heart of the village of Anna Maria, and west of Gulf Drive...there's no better place to be! Only 5 houses from the beach, you'll be steps from the sand AND just moments from shopping, restaurants, the Anna Maria…
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Parking
  • Garage
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$274

3 BR / 2 BA / Sleeps 6

BAY SERA - Anna Maria Island vacation rentals
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$274

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BAY SERA

3 BR / 2 BA / Sleeps 6 | Quick view

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Come to this Island home and "Whatever will be, will be!" Remodeled and tasteful is this 3 bedroom/2 bath home with new heated pool and hot tub in a very private backyard setting. Well appointed with designer finishes throughout. The kitchen is outfitted with gorgeous granite countertops and stainless steel applicanes…
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children
  • Suitable for the elderly

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$171

3 BR / 2 BA / Sleeps 8

1 Reviews

$171

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Island Hideout West: 3BR Family-Friendly Pool Home

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

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Reviews

(1)

This elevated vacation rental has been newly renovated to meet your high standards of vacation home living. With over 1400 square feet of living space, this home boasts three large bedrooms with a king master suite, a queen in the second bedroom, and a twin in the third. A queen sofa bed in the living area provides …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Porch
  • Suitable for children - over five
  • Suitable for the elderly - ask

Details

Reviews

(1)

Perfect!!!

Left on Jun 16, 2014 for a stay in June 2014

The hide out west was awesome! We took our kids, grandkids and parents. We couldn't

have picked a more perfect rental!

I even realized after I was on my way home, I had left my medications and my jewelry behind.....Tura and Sabrina were amazing as they took care of retrieving my belongings and sending them overnight to my home.We are already looking at dates for our next visit to the hide out!

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$332

3 BR / 4 BA / Sleeps 12

17 Reviews

$332

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Harrison Home

3 BR / 4 BA / Sleeps 12 | Quick view
“ Excellent ” 17 Reviews

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Reviews

(17)

The Harrison Home is a very spacious three bedroom, four bath pool home located at 6901 Gulf Drive in Holmes Beach, just 150' to a beautiful sandy beach. Located in the preferred northern end of Holmes Beach, this home features a private pool with fenced yard, poolside gazebo, extensive new landscaping, single car …
  • 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

(17)

great house

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

We had a wonderful stay. The pool was fabulous and it was only a
short walk to the beach. This was our 4th trip to Anna Maria and this
was our favorite rental thus far.

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$165

3 BR / 2 BA / Sleeps 8

1 / 13

$165

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Mermaids Crossing

3 BR / 2 BA / Sleeps 8 | Quick view

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Mermaids Crossing 207 69th Unit B Holmes Beach, Fl. 34217 Mermaids Crossing is a cute-as-a-button newly renovated, ground level 3 bedroom and 2 bathroom private duplex that offers a private heated pool, lush tropical landscaping, fantastic furnishings and so much more! Centrally located on the Island, you are just …
  • Heated Pool
  • High Speed Internet
  • Patio
  • Television
  • DVD Player
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$175

3 BR / 3 BA / Sleeps 7

3 Reviews

$175

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Watch Sunsets, Dolphins, or Just Relax - Bermuda Bay 1453

3 BR / 3 BA / Sleeps 7 | Quick view
“ Excellent ” 3 Reviews

Details

Reviews

(3)

Anna Maria Island boasts one of the longest stretches of sugar white beaches in Florida, and clear, aqua-marine water. Enjoy the natural setting from this spectacular townhouse on Bradenton Beach. This three bedroom, two-and-a-half bath home offers direct Gulf views, a king size master suite, queen size second, two …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Wireless Internet
  • Washing Machine
  • Suitable for children - ask
  • Suitable for the elderly - ask

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Reviews

(3)

Spacious

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

We really enjoyed our stay here. The condo was beautifully decorated. We loved sitting on the deck. The beach is beautiful, and the pool is nice too. The condo is spacious and reasonably priced. It is centrally located. There were sand buckets for the kids which was nice.

The only thing I didn't realize is that you have to cross the street to get to the beach.

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$156

3 BR / 3 BA / Sleeps 6

1 Reviews

$156

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Key Largo Cottage

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

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Reviews

(1)

Key Largo Cottage 315 62nd St. Holmes Beach, Fl. 34217 Step into Key Largo Cottage and feel the sun-drenched, tropical ambience. This newly-constructed cottage has a heated pool complete with swim-up table and waterfall surrounded by lush foliage which creates a private backyard oasis. The inside has beautiful …
  • Heated Pool
  • High Speed Internet
  • Patio
  • Television
  • DVD Player
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Can't wait to go back

Left on Jul 22, 2014 for a stay in July 2014

Anna Maria Island is our new destination. Great place for families traveling with kids of all ages. House was in a great location. Easy 5 min walk to the beach made even easier with the provided metal cart. Toss all your stuff in there and go. Beach is very clean and deep. Great shelling and watch out for the sea turtle nests which are clearly marked.

Comfortable beds, well equipped …

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$285

3 BR / 2 BA / Sleeps 8

18 Reviews

$285

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Tiki

3 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 18 Reviews

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Reviews

(18)

The Tiki, located at 3214 Gulf Drive in Holmes Beach is a spectacular three bedroom, two bath home directly on the emerald waters of the Gulf of Mexico. While the Tiki is located in a very quiet area on a secluded beach area, it is within a five minute walk to shopping and restaurants. Recent renovations include …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Grill
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(18)

Spring Break 2009

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

The house was great! Very clean, everything you would need was supplied with the exception of beach chairs. The location was very easy to get to. The beach beautiful. We arrived early and were given keys to the house as soon as it was released from the cleaning crew.

Our only complaint was a short note stating the water heater was to be replaced on Monday, in our check in package. First guy …

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$285

3 BR / 2 BA / Sleeps 12

22 Reviews

$285

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Breakers 3

3 BR / 2 BA / Sleeps 12 | Quick view
“ Excellent ” 22 Reviews

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Reviews

(22)

Breakers 3, located at 103 45th Street in Holmes Beach. This luxury three-bedroom, two-bath Gulf-front beach home is located in a quiet, secluded area of Holmes Beach. The white sandy beach stretches for miles along the length of the island and spectacular Gulf vistas can be seen from the living room, dining room and …
  • Waterfront
  • 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

(22)

The Beauty of AMI - Breakers 3

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

Breakers 3 is a wonderful property for a family get together. We love AMI and we really love going to Breakers 3.

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$229

3 BR / 3 BA / Sleeps 6

5 Reviews

$229

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A Pearl of a Beach Home with private Pool & Spa

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

Details

Reviews

(5)

*** LARGE HEATED FREE-FORM, LUXURY POOL AND SPA WITH SPACIOUS PAVED SURROUND - AVAILABLE FROM AUGUST 2014 - TOGETHER WITH TROPICAL LANDSCAPING, AUTOMATED GARDEN LIGHTING AND LARGE GROUND FLOOR LANAI. *** Leave your troubles behind as you cross to Anna Maria and surrender to the island pace. Our beach house (a …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(5)

Best vacation in 40 years!

Left on Mar 05, 2014 for a stay in February 2014

The owners, Mike and Lesley Crowther were wonderful to deal with

before, during and after our two week stay at their home. The house

was immaculate and had everything we could have needed during our

stay. Large bedrooms and baths with excellent beds and showers. The

kitchen and laundry room appliances were all in new condition. We

found ourselves wanting to eat in most of the time as the …

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$150

3 BR / 2 BA / Sleeps 8

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$150

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Caribbean Surf

3 BR / 2 BA / Sleeps 8 | Quick view

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Caribbean Surf 306 67th Street Unit B Holmes Beach, Fl 34217 Caribbean Surf is one side of a newly constructed private duplex that offers a discreet backyard with a tropical pool, swim-up Tiki table and BBQ grill. This brand new Island home is equipped with 3 bedrooms and 2 bathrooms and is centrally located on the…
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $125

    3 BR / 2 BA / Sleeps 8

    1 Reviews

    $125

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    Hawaiian Tide

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

    Details

    Reviews

    (1)

    Hawaiian Tide 206 81st Street Unit B Holmes Beach, Fl 34217 Hawaiian Tide is a brand new ground level private duplex with a private heated pool! With tropical landscaping throughout the backyard and pool area you will feel as if you are transported to your own personal island. Centrally located, you have the …
      • Suitable for children - ask
      • Suitable for the elderly - ask

      Details

      Reviews

      (1)

      A beautiful house (looks exactly like the pictures) in paradise.

      Left on Sep 16, 2014 for a stay in August 2014

      Anna Maria is a dream location for any vacation for anyone who wants to relax. People are nice, kind and respectfull. You don´t have to worry about anything, not even transportantion in the Island (it´s free). This house looks like it came out of a magazine. It is gorgeous and so well taken care off. We had a fantastic vacation and want to come back to Annamaria again and again.

      I only …

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      $135

      3 BR / 2 BA / Sleeps 6

      4 Reviews

      $135

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      Palm Cay 5

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

      Details

      Reviews

      (4)

      Palm Cay 5 located at 3000 Gulf Drive in Holmes Beach is a very spacious three bedroom, two bath town home located west of Gulf Drive for easy beach access. The complex features a very large heated pool and onsite laundry room. The complex is about one half block to the beach and is very convenient to shopping and …
      • Shared outdoor pool (unheated)
      • Internet Access
      • Pet friendly - ask
      • Smoking allowed - ask
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      Details

      Reviews

      (4)

      We had a wonderful stay, in a great location, and in a spacious

      Left on Jul 26, 2012 for a stay in July 2012

      We loved the rental property! It was very rencently renovated and the owners must take pride in their property, as they have selected stunning appointments, materials, and finishes for the unit, certainly blowing the majority of its competitors out of the water since most investors merely choose the cheapest and standard "rental" quality materials and finishes. The property is very spacious, …

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      $161

      3 BR / 2 BA / Sleeps 10

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      $161

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      Palm Haven, 3 bedroom

      3 BR / 2 BA / Sleeps 10 | Quick view

      Details

      This beautifully decorated 2 bedroom, 1 bath and 3 bedroom, 2 bath duplex is just a short half block from the white sand beaches of Anna Maria Island. The 2 bedroom unit sleeps 7 people and the 3 bedroom sleeps up to 10 people. Palm Haven is the perfect vacation spot for anyone! Amenities Include: Full kitchen, …
      • Sauna
      • Internet Access
      • Washing Machine
      • Clothes Dryer
      • Outdoor Dining Area
      • Pet friendly
      • Suitable for children
      • Suitable for the elderly

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      $285

      3 BR / 2 BA / Sleeps 6

      17 Reviews

      $285

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      Franks Beach House

      3 BR / 2 BA / Sleeps 6 | Quick view
      “ Excellent ” 17 Reviews

      Details

      Reviews

      (17)

      Franks Beach House is a beautiful three bedroom, two bath direct Gulf front home located at 3212 Gulf Drive in Holmes Beach. It features a very large open deck facing the beach as well as a screened lanai for when you want a little shade. The expansive beach stretches for miles in either direction.This spacious and …
      • Waterfront
      • Ocean or water views
      • Internet Access
      • Grill
      • Pet friendly
      • Smoking allowed - ask
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      Details

      Reviews

      (17)

      Spacious home with very good location

      Left on Dec 30, 2010 for a stay in December 2010

      Excellent location right on beautiful beach within walking distance of shopping center. The new deck is a great addition. Home is generously layed out, well equipped with dishes, cutlery, linens and blankets, as well as beach equipment. Home is older and has not been updated in recent years other than the deck. The couch is a back breaker.

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      $214

      3 BR / 2 BA / Sleeps 6

      1 / 23

      $214

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      Havana Cay

      3 BR / 2 BA / Sleeps 6 | Quick view

      Details

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

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      $229

      3 BR / 2 BA / Sleeps 8

      1 / 22

      $229

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      Sandcastle 8

      3 BR / 2 BA / Sleeps 8 | Quick view

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      SandCastle # 8 (Maui Cove) 200 Gulf Dr. South Unit #8 Bradenton Beach, Fl. 34217 Maui Cove- the name says it all. This luxury 3 bedroom, 2 bathroom direct Gulf front condo brings a unique and fun Hawaiian style atmosphere. From the decorative surf boards displayed on the way, to the Island Tropical furniture…
        • Suitable for children - ask
        • Suitable for the elderly - ask

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        $250

        3 BR / 3 BA / Sleeps 6

        1 Reviews

        $250

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        Anna Maria Cottage

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

        Details

        Reviews

        (1)

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

          Details

          Reviews

          (1)

          Great location!

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

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

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          $150

          3 BR / 3 BA / Sleeps 8

          1 / 28

          $150

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          Calypso Cottage

          3 BR / 3 BA / Sleeps 8 | Quick view

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          Calypso Cottage 515 42nd St. Holmes Beach, Fl. 34217 Calypso Cottage is a stylish Mediterranean beach villa with all the finishing touches of what you would expect from an exquisite Anna Maria vacation home. Only a 5 minute stroll to the beach, the focal point has to be the brand new elaborate pool which wraps …
          • Heated Pool
          • High Speed Internet
          • Patio
          • Television
          • DVD Player
          • Suitable for children - ask
          • Suitable for the elderly - ask

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          $159

          3 BR / 2 BA / Sleeps 6

          1 / 30

          $159

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          Island living at it's best!

          3 BR / 2 BA / Sleeps 6 | Quick view

          Details

          Adorable, ground level, vintage cottage with modern conveniences and private pool is all you could desire for a vacation. Tasteful décor, comfortable furnishings and peaceful surroundings await. 3 bedroom, 2 bath sleeps 6. Blocks from the gulf. Additional amenities include: washer & dryer.
          • Internet Access
          • Washing Machine
          • Clothes Dryer
          • A/C or climate control
          • Deck
          • Suitable for children - ask
          • Suitable for the elderly - ask
          • Wheelchair accessible - ask

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          $235

          3 BR / 3 BA / Sleeps 8

          1 / 22

          $235

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          Beachside

          3 BR / 3 BA / Sleeps 8 | Quick view

          Details

          The Beachside is a custom built three bedroom, two bath pool home located at 113 31st Street in Holmes Beach. This spectacular home is west of Gulf Drive for easy beach access with no busy streets to cross. The pool area is tropical and spacious with a charcoal grill for you enjoyment. It’s surrounded by swaying …
          • 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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          $236

          3 BR / 3 BA / Sleeps 10

          6 Reviews

          $236

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          BAREFOOTBLISS

          3 BR / 3 BA / Sleeps 10 | Quick view
          “ Excellent ” 6 Reviews

          Details

          Reviews

          (6)

          Coastal living in a tropical setting! Gorgeous ground level 3 bedroom/3 bath home with designer touches at every glance. This light and airy, open-concept floor plan is generously appointed with flat screen TVs in all rooms and tile floors throughout every one of its almost 2000 square feet. You will be pleased to …
          • Shared outdoor pool (unheated)
          • A/C or climate control
          • Parking
          • Grill
          • Satellite or cable TV
          • Suitable for children
          • Suitable for the elderly

          Details

          Reviews

          (6)

          It was like a little bit of paradise.

          Left on Nov 21, 2013 for a stay in May 2013

          The home was beautiful and very comfortable. The pool is georgeous and easily accessible from the home. The beach is only a short walk from the home.

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          $67

          3 BR / 3 BA / Sleeps 8

          6 Reviews

          $67

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          Cove at Sandy Pointe 111

          3 BR / 3 BA / Sleeps 8 | Quick view
          “ Very Good ” 6 Reviews

          Details

          Reviews

          (6)

          The Cove at Sandy Pointe 111, located at 3601 East Bay Drive in Holmes Beach is an exceptional three bedroom, three bath bay front unit. Located directly on the bay in a quiet location, this unit overlooks a natural mangrove preserve. The complex features a large heated pool.This spacious unit sleeps eight with a king…
          • Waterfront
          • 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

          Details

          Reviews

          (6)

          We had a wonderful time on anna Maria

          Left on Mar 14, 2012 for a stay in February 2012

          3 Bedrooms 3 baths, 3 balconies-what could be better for 2 couples sharing a relaxing month on anna Maria? Master bedroom is huge with a king bed and a pull out couch. Checkin was flawless and service was great-altho there were a few minor problems. Condo had not been cleaned as described, heat was off and then air conditioning needed service--this was taken care of immediately and did not …

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          $214

          3 BR / 2 BA / Sleeps 8

          1 Reviews

          $214

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          AMI Retreat: 3BR Pool Home 200 Steps from Beach

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

          Details

          Reviews

          (1)

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

          Details

          Reviews

          (1)

          Relaxing

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

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

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

          I highly recommend this …

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          $274

          3 BR / 2 BA / Sleeps 6

          1 / 34

          $274

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          BEACHWALK

          3 BR / 2 BA / Sleeps 6 | Quick view

          Details

          Three bedroom, two bath totally redone home with gorgeously landscaped backyard and heated pool! Only houses to the Gulf of Mexico and a beautiful white sand stretch of beach! This home has been updated with Mexican tile, granite countertops, and stainless kitchen! King-sized master bedroom, second queen-sized bedroom…
          • 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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          $208

          3 BR / 2 BA / Sleeps 8

          1 / 25

          $208

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          Mango Bay

          3 BR / 2 BA / Sleeps 8 | Quick view

          Details

          Mango Bay 417 Clark Dr. Holmes Beach, Fl. 34217 Mango Bay is not your average vacation rental- it is much more. It is a custom built, elevated 4 bedroom, 2 full bathrooms, 2 half bath, private villa with heated pool and deluxe hot tub (it has it's own table built in). It Includes a huge master suite on second …
          • Private Pool
          • High Speed Internet
          • Patio
          • Television
          • DVD Player
          • Suitable for children - ask
          • Suitable for the elderly - ask

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          $125

          3 BR / 2 BA / Sleeps 8

          1 / 15

          $125

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          Mermaids Watch

          3 BR / 2 BA / Sleeps 8 | Quick view

          Details

          Mermaids Watch 207 69th St. Unit A Holmes Beach, Fl. 34217 This brand new ground level duplex features 3 bedrooms and 2 baths, a private heated pool with spa and swim up table, and is only a short 2 minute stroll to the Gulf beach. Professionally decorated and outfitted with fine fixtures, travertine marble, …
          • Private 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 10

          1 / 18

          $200

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          Island Life

          3 BR / 2 BA / Sleeps 10 | Quick view

          Details

          Island Life 108 78th St. Holmes Beach, Fl. 34217 The name says it all. Just a stone's throw away from the sugar white sand beaches of the Gulf of Mexico. You almost don't even need to leave the front yard to enjoy a full sunset! This ground level home has 3 bedrooms and 2 bathrooms. The home sits on a large lot…
          • 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 / 22

          $200

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          Villa Sand Dollar

          3 BR / 2 BA / Sleeps 6 | Quick view

          Details

          Villa Sand Dollar 113 75th Street Holmes Beach, Fl. 34217 Newly remodeled and a perfect location! This Island retreat offers 3 bedrooms, 2 1/2 baths and is a very short walk to the Gulf beach. The home sits West of Gulf Dr, only 5 houses in from the beach and about a 30 second walk! Offering views of the Gulf …
          • Outdoor Pool
          • Internet Access
          • Dishwasher
          • Suitable for children - ask
          • Suitable for the elderly - ask

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          $241

          3 BR / 2 BA / Sleeps 8

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          Island Paradise 6

          3 BR / 2 BA / Sleeps 8 | Quick view

          Details

          Island Paradise #6 3708 Gulf Drive #6 Holmes Beach, Fl. 34217 Island Paradise is just that- the best view on Anna Maria Island. Panoramic views of the beautiful blue waters of the Gulf of Mexico and the white sand beaches. And don't forget the legendary sunsets. It simply does not get any better than this. …
          • Shared outdoor pool (unheated)
          • Internet Access
          • Dishwasher
          • Suitable for children - ask
          • Suitable for the elderly - ask

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          $171

          3 BR / 2 BA / Sleeps 9

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          Starfish

          3 BR / 2 BA / Sleeps 9 | Quick view

          Details

          Starfish 105 79th Street Holmes Beach, Fl 34217 Location, location, location! This home is literally just steps to the beach- about a 30 second walk! It sits one house in, at the end of a dead-end, very quiet street. It just does not get much more convenient than this. It has 3 bedrooms and 2.5 baths, is bright…
          • Internet Access
          • Dishwasher
          • Suitable for children - ask
          • Suitable for the elderly - ask

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          $200

          3 BR / 2 BA / Sleeps 8

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          Anna Maria Chateau

          3 BR / 2 BA / Sleeps 8 | Quick view

          Details

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

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            $550

            3 BR / 2 BA / Sleeps 6

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            Serendipity

            3 BR / 2 BA / Sleeps 6 | Quick view

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            Serendipity 789 North Shore Drive Anna Maria, Fl. 34216 GULF FRONT HOME - "Serendipity" - Just as its name implies: "A pleasant surprise"! Enjoy coastal living at its best. Newly renovated private home that still embraces that "Old Florida" charm with high end quality decor and furnishings This 3 bedroom 1.…
            • Internet Access
            • Dishwasher
            • Suitable for children - ask
            • Suitable for the elderly - ask

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            $156

            3 BR / 3 BA / Sleeps 9

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            Villa Monica

            3 BR / 3 BA / Sleeps 9 | Quick view

            Details

            Villa Monica 4108 6th Avenue Holmes Beach, FL 34217 This beautiful Mediterranean Villa has recently undergone a full renovation which includes a brand new tropical pool, pool furniture, all new kitchen with new granite counter-tops and stainless steal appliances, cookware and dinnerware. All new furniture, …
            • Outdoor Pool
            • Internet Access
            • Dishwasher
            • Suitable for children - ask
            • Suitable for the elderly - ask

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            $150

            3 BR / 3 BA / Sleeps 6

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            Seabreeze Cottage

            3 BR / 3 BA / Sleeps 6 | Quick view

            Details

            Seabreeze Cottage 5009 2nd Avenue Holmes Beach FL. 34217 This gorgeous property is nestled in a quiet residential neighborhood West of Gulf Dr, just over one block to the beach access. Seabreeze Cottage is just a one to two minute stroll to the beach. This pretty 3 bedroom/3 bathroom property is newly landscaped…
            • Heated Pool
            • High Speed Internet
            • Patio
            • Television
            • DVD Player
            • Suitable for children - ask
            • Suitable for the elderly - ask

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            $171

            3 BR / 2 BA / Sleeps 6

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            Sea Breeze Pool Home

            3 BR / 2 BA / Sleeps 6 | Quick view

            Details

            Sea Breeze is a private home with 3 bedrooms and 2 bathrooms and a brand new heated pool! The home is comfortable and well stocked. Wood floors throughout, open floor plan and cathedral ceilings with large sliders that open onto a large screened porch. Close proximity to the beach, about 3 blocks. Located in …
            • Internet Access
            • Washing Machine
            • Clothes Dryer
            • A/C or climate control
            • Central heating
            • Suitable for children
            • Suitable for the elderly - ask

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            $167

            3 BR / 2 BA / Sleeps 6

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            Island Paradise 5

            3 BR / 2 BA / Sleeps 6 | Quick view

            Details

            Island Paradise #5 3708 Gulf Drive #5 Holmes Beach, Fl 34217 This property is only available for a minimum 1 month rental from January, 2014 through April, 2014 and 2015. Please see approximate monthly rates below (rates do not include any taxes or cleaning fees). Please call our office at 941-778-4178 for more …
            • Shared outdoor pool (unheated)
            • Suitable for children - ask
            • Suitable for the elderly - ask

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            $215

            3 BR / 2 BA / Sleeps 8

            1 Reviews

            $215

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            Island Paradise 2

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

            Details

            Reviews

            (1)

            Island Paradise Unit # 2 3708 Gulf Dr. Unit # 2 Holmes Beach, Fl. 34217 This beautiful Gulf front condo makes you feel like you are living right on top of the beautiful blue waters of the Gulf of Mexico. The entire living area and kitchen are facing west with lots of crystal blue water in front and the master …
            • Shared outdoor pool (unheated)
            • High Speed Internet
            • Patio
            • Television
            • DVD Player
            • Suitable for children - ask
            • Suitable for the elderly - ask

            Details

            Reviews

            (1)

            I would go back Tomorrow if I could

            Left on Oct 14, 2014 for a stay in October 2014

            Finally a villa that looks exactly like the pictures. It was very clean, felt new, good views and on the beach. We were very lucky in that we had we were the only ones in the 6 apartment condo so the place was very quite. Bedroom 1 was very nice with a large bed and tv although the shower could have been better, room 2 had 2 beds and a tv, room 3 was a queen but strangely didn't have a tv (this …

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            $170

            3 BR / 2 BA / Sleeps 6

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            Jacaranda Artist Retreat

            3 BR / 2 BA / Sleeps 6 | Quick view

            Details

            As an artist this private three bedroom and two bath elevated vacation home has been a retreat that inspires many paintings of Anna Maria Island. Located on the secluded North End you will enjoy the tranquility of the Island and have an easy stroll to the Gulf of Mexico and the best white sugar-sand beach. You can …
            • Wireless Internet
            • Washing Machine
            • Clothes Dryer
            • Outdoor Dining Area
            • A/C or climate control
            • Pet friendly - ask
            • Suitable for children - over five
            • Suitable for the elderly - ask

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            $143

            3 BR / 3 BA / Sleeps 6

            2 Reviews

            $143

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            Villa Tuscany

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

            Details

            Reviews

            (2)

            Villa Tuscany 4110 6th Avenue Holmes Beach, FL 34217 The enchanting Villa Tuscany is nestled in gated tropical gardens with views towards the Bay waters of Anna Maria Sound. Walls are topped with decorative Italian style balustrading and brightly covered bougainvillea along with flowering hibiscus surrounding …
            • Heated Pool
            • High Speed Internet
            • Patio
            • Dishwasher
            • Television
            • Suitable for children - ask
            • Suitable for the elderly - ask

            Details

            Reviews

            (2)

            Nice place

            Left on Jul 08, 2009 for a stay in January 2009

            We had a great stay. The Villa was large enough for all 8 of us. The pool was nice. The grocery store and the beach were in walking distance. We didn't realize there are stairs down to the kitchen. With 2 small grandchildren and my mother who has trouble with stairs this caused some problems. Baby gates would have solved the problem, 1 for the stairs to the kitchen, 1 for the stairs to the …

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            $236

            3 BR / 2 BA / Sleeps 10

            2 Reviews

            $236

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            DOLPHIN COTTAGE

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

            Details

            Reviews

            (2)

            Gorgeous, remodeled home on the west side of Gulf Drive, no streets to cross to the Gulf of Mexico! Queen-sized master bedroom with Flat screen TV/DVD and quiet patio, Queen in Second Bedroom with Flat Screen TV/DVD and patio to pool area, and 2 twin trundle beds in guest room with Flat screen TV/DVD and Game Cube, …
            • Shared outdoor pool (unheated)
            • A/C or climate control
            • Parking
            • Grill
            • Suitable for children
            • Suitable for the elderly

            Details

            Reviews

            (2)

            The best place in Holmes Beach-the best place I have stayed in

            Left on Nov 29, 2013 for a stay in July 2012

            This place is heaven. So close to the beach on anna maria island that most people have never heard of. This house is so great and fully furnished. It was/and still is my dream vacation home!!! It is close to all things. Close especially to beach, but many, many stores and restaurants! This is a great place for great memories. The home is gorgeous, large kitchen. Many places to sleep and …

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            $285

            3 BR / 3 BA / Sleeps 8

            25 Reviews

            $285

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            Breakers 1

            3 BR / 3 BA / Sleeps 8 | Quick view
            “ Excellent ” 25 Reviews

            Details

            Reviews

            (25)

            Escape to the Breakers, one of the finest luxury gulf front vacation homes on Anna Maria Island, located at 102 31st Street in Holmes Beach. Enjoy the tropical breezes and aqua-blue surf from the deck overlooking the white sand beach and sparkling Gulf of Mexico. Watch the dolphins cavort in the surf. Relax at the end…
            • Waterfront
            • 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

            (25)

            Beautiful beachfront home

            Left on Feb 24, 2009 for a stay in August 2008

            The house was great. The beach was right outside the door and fairly private. The home was nicely decorated, but had a few maintenance issues. The description states sleeps eight, but our party of eight found it to be a bit crowded. We made it work, but others may not be satisfied. Over all I would recommend this property.

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            $200

            3 BR / 2 BA / Sleeps 6

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            Its My Dream

            3 BR / 2 BA / Sleeps 6 | Quick view

            Details

            It's My Dream 5607 Carissa Street Holmes Beach, Fl. 34217 It's My Dream is a brand new and lovely island-themed private duplex with 3 bedrooms and 2 bathrooms. Equipped with a private heated pool, spa and spacious deck-this home truly represents the best of what Anna Maria Island has to offer. Centrally located …
              • Suitable for children - ask
              • Suitable for the elderly - ask

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              $156

              3 BR / 2 BA / Sleeps 6

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              Shades of Surf

              3 BR / 2 BA / Sleeps 6 | Quick view

              Details

              Shades of Surf 213 65th Street Holmes Beach, 34217 Shades of Surf is a newly remodeled 3 bedroom and 2.5 bathroom home with a private heated pool and outdoor spa. This property is only a short 2 minute walk away from the beach and it is closely located to the Island shops and conveniences. Equipped with an …
              • Outdoor Pool
              • Internet Access
              • Dishwasher
              • Suitable for children - ask
              • Suitable for the elderly - ask

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              $125

              3 BR / 2 BA / Sleeps 8

              1 / 13

              $125

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              Tropic Dream

              3 BR / 2 BA / Sleeps 8 | Quick view

              Details

              Tropic Dream 5606 Holmes Blvd Holmes Beach, Fl. 34217 This is a newly renovated, ground level 3 bedroom, 2 bathroom home is only a short 2-3 minute walk to the beach. Surrounded by lush tropical landscaping, the home has a private heated pool and plenty of sunshine! It is the South unit of the duplex. There is…
              • Heated Pool
              • High Speed Internet
              • Patio
              • Television
              • Suitable for children - ask
              • Suitable for the elderly - ask

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              $200

              3 BR / 3 BA / Sleeps 10

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              Aloha Home

              3 BR / 3 BA / Sleeps 10 | Quick view

              Details

              This beautiful 2200 sq ft beach home was built in 2006 and has all the modern luxuries including; an elevator, solid wood cabinets, granite countertops, wood floors, carpet in bedrooms, dishwasher, garbage disposal, 3 large bedrooms, 2 ½ baths, Jacuzzi tub in master bathroom, private heated pool, deck overlooking …
              • Internet Access
              • Housekeeping Optional
              • Washing Machine
              • Clothes Dryer
              • Outdoor Dining Area
              • Suitable for children
              • Suitable for the elderly
              • Wheelchair accessible - ask

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              $220

              3 BR / 2 BA / Sleeps 8

              1 Reviews

              $220

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              Sans Souci Up

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

              Details

              Reviews

              (1)

              Views, views, views! You will love watching the waves and the sunset over the sandy Gulf beach—one hundred steps away—as well as the boats and the sunrise over the Bay. Located at 102 6th Street South in Bradenton Beach, this beautiful and comfortable beach property is an easy walk to historic Bridge Street with …
              • 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

              Details

              Reviews

              (1)

              Wonderful rental, great location, Love the place!!

              Left on Jan 24, 2015 for a stay in December 2014

              We actually rented this unit last Feb and loved it so much that we came back down in Dec. The owners were very gracious (rented from them the first time) and the rental company was great (second time). My mom has dementia, early stages, so the elevator worked beautifully for us. We weren't concerned about her wandering outside as the outside stairs were too much for her and she didn't know how to…

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