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$143

2 BR / 2 BA / Sleeps 4

Have breakfast with the dolphins. Spacious 2BR/2BA condo overlooking Anna Maria Sound. - Holmes Beach vacation rentals
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$143

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Have breakfast with the dolphins. Spacious 2BR/2BA condo overlooking Anna Maria Sound.

2 BR / 2 BA / Sleeps 4 | Quick view

Details

This extremely bright condo offers everything you could hope for in a seasonal rental property. Brilliant morning sun fills the living areas of this spacious unit. The kitchen is fully equipped and the family room features a raised seating area ideal for entertaining or watching the dolphins swam by in Anna Maria …
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$240

3 BR / 2 BA / Sleeps 6

2 Reviews

$240

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SANDY FEET

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

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Reviews

(2)

Beautiful, brand new, 3 bedroom/2.5 bath townhouse home with decorator furnishings throughout! Comfortable and roomy with great room, large open lanai, two car garage, and beautiful open kitchen area with granite countertops. Great central location a couple of blocks to the beach, and easily accessible to the free …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly

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Reviews

(2)

Perfect Beach Vacation House!

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

We absolutely loved this home! Loved the decorations - very fun, colorful, artistic and interesting but absolutely gorgeous. The house is less than half a mile comfortable walk to the beach. It is also right across from a trolley stop.

We have been to anna Maria several times, and we have stayed at many very nice properties. This is definitely one of our favorites.

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$124

2 BR / 2 BA / Sleeps 6

Beach Isle - Holmes Beach vacation rentals
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$124

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Beach Isle

2 BR / 2 BA / Sleeps 6 | Quick view

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Beach Isle 304 58th st. Holmes Beach, Fl. 34217 This newly constructed private 2/2 home is perfect for your island vacation getaway! Lounge by your tropical private, heated pool or on our white sandy beaches, the choice is yours with this versatile home! Centrally located to local restaurants and beaches, you are …
  • Heated Pool
  • High Speed Internet
  • Patio
  • Television
  • DVD Player
  • Suitable for children - ask
  • Suitable for the elderly - ask

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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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$200

3 BR / 2 BA / Sleeps 6

1 Reviews

$200

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Gulf Place 2A

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

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Reviews

(1)

Gulf Place 2A 6700 Gulf Drive #2 Holmes Beach, Fl 34217 Direct Gulf front newly remodeled 3 bedroom, 2 bath condo with large open covered balcony. Breathtaking views of the Gulf of Mexico right out your window . Bright and light and very inviting and features a large open balcony, updated kitchen and breathtaking…
  • Outdoor Pool
  • Internet Access
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Amazing view.

Left on Dec 10, 2014 for a stay in November 2014

The selling point of this condo is definately the long balcony which fronts onto the beach giving spectacular panoramic views - great for breakfasts and sunsets especially. We were pleasantly surpised by the interior as well which was tastefully decorated and all felt quite high-spec. The kitchen / dining area is particularly nice but it was all good. When we booked there were no reviews for this…

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$285

3 BR / 3 BA / Sleeps 8

26 Reviews

$285

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Breakers 1

3 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 26 Reviews

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Reviews

(26)

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

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Reviews

(26)

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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$250

4 BR / 3 BA / Sleeps 8

1 Reviews

$250

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Summer Breeze

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

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Reviews

(1)

Summer Breeze 313 61st Street Holmes Beach, Fl 34217 Elevated three story Key West style home with all high end finishes including: solid granite surfaces, solid wood cabinets with ceramic tile in living areas and custom wood on the staircase and in the Master bedroom. Located in a quiet residential neighborhood …
    • Suitable for children - ask
    • Suitable for the elderly - ask

    Details

    Reviews

    (1)

    Everything you need for a relaxing AMI vacation

    Left on Dec 05, 2014 for a stay in November 2014

    Overall, the house is spacious, comfortable and had everything we needed for our week long stay. It is nicely decorated. The beach is several blocks away but still within walking distance. Everyone at the property management company was wonderful and easy to deal with. Which I was especially grateful for since we were coordinating with multiple couples coming from multiple locations. The Wi-Fi …

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    $150

    4 BR / 4 BA / Sleeps 8

    1 / 21

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    Sunbow Bay 1B

    4 BR / 4 BA / Sleeps 8 | Quick view

    Details

    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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    $110

    2 BR / 2 BA / Sleeps 8

    2 Reviews

    $110

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    Hammock Haven

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

    Details

    Reviews

    (2)

    Hammock Haven is a wonderful two bedroom two bath home located at 2702 Avenue C in Holmes Beach. This two story beach get away has a distant gulf view and a peek at the bay. Hammock Haven is close to dining, beach, trolley, and the bay. Stroll the beaches, fish the bay, and explore the many treasures that Anna Maria …
    • 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

    (2)

    We love anan Maria Island

    Left on Jul 31, 2010 for a stay in July 2010

    We love the house. It is on a dead end street which is great if you have kids. The downstairs rooms smelled a little moldy we guess because no one was there and the ac was not being used. Upstairs we love! The second room should have two full size beds or trundle pull out beds for more sleeping space. We would come back!

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    $171

    2 BR / 2 BA / Sleeps 4

    1 Reviews

    $171

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    Gulf View: 2BR Beachfront Condo with Amazing View

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

    Details

    Reviews

    (1)

    Once you open the door to this Gulf View, you will begin to relax. Restful and soothing beach colors throughout this two-bedroom, two-bath condo will encourage you to have a fabulous vacation on Anna Maria Island. The breathtaking view of the sparkling water through floor to ceiling windows in the open living area …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Suitable for the elderly

    Details

    Reviews

    (1)

    Oh, what a view!

    Left on May 05, 2014 for a stay in April 2014

    Gulf View was clean, comfortable and "homey". We had a great week there this april! The view is, no question, outstanding ! The condo was clean and comfortable, the beds were fine, bathrooms terrific, kitchen fully stocked with everything we needed. Great place !

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    $196

    3 BR / 2 BA / Sleeps 6

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    $196

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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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    $156

    3 BR / 3 BA / Sleeps 8

    1 Reviews

    $156

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    Palm Villa

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

    Details

    Reviews

    (1)

    Palm Villa 307 63rd St. Holmes Beach, Fl. 34217 Palm Villa is New England style cottage and Florida Keys getaway all rolled into one. The vaulted main room ceiling gives this newly constructed home a wide-open feel while the shabby chic furnishings create a cozy atmosphere. The tropical foliage around the …
    • Heated Pool
    • High Speed Internet
    • Patio
    • Television
    • DVD Player
    • Suitable for children - ask
    • Suitable for the elderly - ask

    Details

    Reviews

    (1)

    Wonderful Rental for 2 families!

    Left on Jul 12, 2009 for a stay in March 2009

    We rented this home for a full week! It was clean and ready when we arrived and was the perfect place to share with another family! The Bedrooms and bathrooms are spacious and inviting! The kitchen is "just like home"! We enjoyed spending time on the the deck outdoors and loved the convenient 1 block walk to the beach!
    We really didn't have any complaints, but would've enjoyed nicer quality…

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    $79

    2 BR / 2 BA / Sleeps 4

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    $79

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    Sand Dollar Villa

    2 BR / 2 BA / Sleeps 4 | Quick view

    Details

    This 2 bedroom, 2 bath villa is in the heart of Anna Maria Island. It is located 500 feet to the beach in a residential neighborhood, west of Gulf Drive. Decorated with simplicity, it is fully equipped with all the amenities which include: Full kitchen, washer/dryer, microwave, dishwasher, cable tv, VCR, phone, …
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • A/C or climate control
    • Central heating
    • Suitable for children
    • Suitable for the elderly

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    $105

    1 BR / 1 BA / Sleeps 4

    15 Reviews

    $105

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    Palm Cay 1

    1 BR / 1 BA / Sleeps 4 | Quick view
    “ Very Good ” 15 Reviews

    Details

    Reviews

    (15)

    Palm Cay Condominium #1 is located at 3000 Gulf Drive in Holmes Beach, on the west side of the street for easy beach access. The complex offers a heated pool and an on site coin operated laundry room for your convenience. It’s a short stroll to shopping and restaurants and the beach is less than two minutes away. …
    • 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

    (15)

    cozy, great location and affordable

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

    Nice home with a cozy feel. convienent location to beach and stores. Pool was clean and quiet. Nice layout and room to bq on side lawn. We rented bikes and biked the area never using our car. Clean, good size rooms and well kept property.Nice laundry area as well. Easy walk to the beach.
    The busy road was a bit of a draw back since our unit fronted the road.

    We would rent this unit again.

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    $129

    1 BR / 1 BA / Sleeps 4

    1 / 19

    $129

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    Shell Haven

    1 BR / 1 BA / Sleeps 4 | Quick view

    Details

    Shell Haven 101 73rd St. Unit #4 Holmes Beach, Fl 34217 Direct Beachfront- steps to the beach! Shell Haven is a lovely 1 bedroom and 1 bathroom Gulf front condo that has been completely renovated top to bottom. This ground floor unit is just steps away from the pristine white sand beaches and features a west-facing…
    • Dishwasher
    • Suitable for children - ask
    • Suitable for the elderly - ask

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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

    Details

    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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    $200

    3 BR / 3 BA / Sleeps 10

    1 Reviews

    $200

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    Aloha Home

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

    Details

    Reviews

    (1)

    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

    Details

    Reviews

    (1)

    Nice house but not suited for us. Gulf Bay Realty was great.

    Left on Mar 29, 2015 for a stay in March 2015

    The Aloha house was nice but not the best set up for our group. The elevator was a necessity for us and it worked wonderfully. Having the grill on the main level and the kitchen on the 2nd floor was a pain. We only grilled out one night...too much of a hassle for us. Might be OK for others its just not something we are used too. The master bed and bath are are the 2nd floor. The master bath was …

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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 …
    • Outdoor 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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    $160

    4 BR / 2 BA / Sleeps 8

    1 / 18

    $160

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    Hawaiian Hideaway

    4 BR / 2 BA / Sleeps 8 | Quick view

    Details

    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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      $115

      2 BR / 2 BA / Sleeps 4

      4 Reviews

      $115

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      Sunbow Bay 114

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

      Details

      Reviews

      (4)

      Sunbow Bay Condominium #114 located at 3705 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, elevators, undercover parking and every conceivable …
      • Shared outdoor pool (unheated)
      • Internet Access
      • Pet friendly
      • Smoking allowed - ask
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      Details

      Reviews

      (4)

      Sun & Fun

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

      Nice clean Property, would stay there again,
      The Internet has allowed us to view properties,
      Prices etc. before booking. Agents for our
      rentals have been very helpful.

      Note' We travel all over the North Americal
      continent, if we are in the Bradenton Fl. area we will defentely look you up again.

      Jim Branchfloer

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      $162

      2 BR / 2 BA / Sleeps 6

      1 / 23

      $162

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      CASA SIERRA 205B

      2 BR / 2 BA / Sleeps 6 | Quick view

      Details

      Casa Sierra Resort is a private Mediterranean style four unit complex in the heart of Anna Maria Island with just a two minute walk to the beautiful white sand beach! Each unit offers an outdoor patio with the spacious common area providing a large heated pool, gazebo, lush tropical landscaping, and picnic tables …
      • Internet Access
      • Washing Machine
      • Clothes Dryer
      • Outdoor Dining Area
      • A/C or climate control
      • Pet friendly
      • Suitable for children
      • Suitable for the elderly

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      $114

      2 BR / 2 BA / Sleeps 6

      1 / 24

      $114

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      A Hidden Gem: 2BR Family-Friendly Condo with Pool

      2 BR / 2 BA / Sleeps 6 | Quick view

      Details

      Note: This property requires a 28-day minimum stay. This two-bedroom, two-bath vacation rental is the perfect size for a romantic getaway, small families or close friends. Located in the Westbay Point & Moorings condominium complex in Holmes Beach, this hidden gem is tucked away from traffic, offering tranquility, …
      • Waterfront
      • Washing Machine
      • Clothes Dryer
      • A/C or climate control
      • Patio
      • Suitable for children

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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

      Details

      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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      $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

      Details

      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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      $175

      2 BR / 2 BA / Sleeps 4

      2 Reviews

      $175

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      Playa Encantada 112

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

      Details

      Reviews

      (2)

      Playa Encantada 112 is a gorgeous two bedroom, two bath direct Gulf front complex, located at 6006 Gulf Drive in Holmes Beach. This popular complex features an elevator, heated pool, jacuzzi, 2 tennis courts and shuffle board. The open balcony gives you a view of the gulf.The living room features a 32” flat …
      • 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

      (2)

      Great location. Very relaxing.

      Left on Aug 01, 2013 for a stay in July 2013

      Very nice and relaxing family vacation. Ideal for families with young kids. All the amenities of home just steps to the beach. Will definitely return.

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      $229

      3 BR / 2 BA / Sleeps 6

      1 / 14

      $229

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      The Beach Front

      3 BR / 2 BA / Sleeps 6 | Quick view

      Details

      The Beachfront 3302 Gulf Drive, Unit 101 Holmes Beach, FL 34217 This three bedroom, two bathroom direct Gulf front vacation property is one of a select group of just five beachfront condos, close to Bradenton Beach and the old fishing village of Cortez. Walk out on to your own beachfront balcony to watch the …
      • Shared outdoor pool (unheated)
      • High Speed Internet
      • Patio
      • Television
      • DVD Player
      • 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

      Details

      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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      $156

      3 BR / 2 BA / Sleeps 8

      1 Reviews

      $156

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      Aloha Home

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

      Details

      Reviews

      (1)

      Aloha Home 206 55th Street Holmes Beach, Fl. 34217 This is a gorgeous 3 bedroom, 2 bath home with a heated pool. Spectacular and unsurpassed tropical landscaping surrounds the entire home - especially the private pool area. The outdoor paver patio is partially covered for a break from the sun, or to cool off in …
      • Heated Pool
      • High Speed Internet
      • Patio
      • Television
      • DVD Player
      • Suitable for children - ask
      • Suitable for the elderly - ask

      Details

      Reviews

      (1)

      Beautiful and comfortable place to stay.. Had every everything!

      Left on Feb 19, 2015 for a stay in December 2014

      We loved the Aloha home. Perfect location.. beach.. shopping. relaxing. only one thing that was disappointing was the pool temperature. it really was not heated. Owners controlled the temp. I was very cold! We called and they did nothing!!

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      $159

      2 BR / 2 BA / Sleeps 6

      7 Reviews

      $159

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      LOGGERHEAD

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

      Details

      Reviews

      (7)

      Perfect 2 bedroom/2 bath, with a private HEATED pool in a very lush tropical setting. Loggerhead is just a couple of blocks to the beach, and the free island Trolley! The front entry takes you right into the open great room where the entire family can hang out and talk about the great time they are having on the …
      • Internet Access
      • Washing Machine
      • Clothes Dryer
      • Outdoor Dining Area
      • A/C or climate control
      • Pet friendly
      • Suitable for children
      • Suitable for the elderly

      Details

      Reviews

      (7)

      The best anna Maria has to offer!

      Left on Aug 27, 2013 for a stay in September 2012

      After our many frequent stays on the island, we have found this is the best value and amenities for our needs!
      This home is amazing: We have not wanted for anything while here and love the location.
      And, the rental agency has fulfilled our needs for 5 years...we have been coming to aMI for 13 years and this is the best, most knowledgeable staff on the island!
      You will not find a better equipped …

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      $125

      3 BR / 2 BA / Sleeps 6

      1 / 19

      $125

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      Peacock Crossing

      3 BR / 2 BA / Sleeps 6 | Quick view

      Details

      Peacock Crossing 205 Unit B Peacock Lane Holmes Beach, Fl 34217 Peacock Crossing is a newly renovated ground level duplex that features 3 bedrooms and 2 bathrooms and a private heated pool with swim-up Tiki table. Tucked away on a quiet residential street this cute as a button, Island bungalow is only a 5-7 minute …
        • Suitable for children - ask
        • Suitable for the elderly - ask

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        $143

        2 BR / 1 BA / Sleeps 4

        1 / 11

        $143

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        Kims Kottage West

        2 BR / 1 BA / Sleeps 4 | Quick view

        Details

        Kim's Kottages West 205W 75th Street Holmes Beach, FL 34217 ISLAND DUPLEX-This totally updated 2 bedroom and 1 bathroom ground level duplex is just a short 2 minute walk away from the stunning white sandy beaches of the Gulf of Mexico. If you are looking for a quiet retreat away from it all than look no further. …
        • Shared outdoor pool (unheated)
        • Internet Access
        • Dishwasher
        • 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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        $250

        3 BR / 2 BA / Sleeps 6

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        $250

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        Coastal Sunset

        3 BR / 2 BA / Sleeps 6 | Quick view

        Details

        Coastal Sunset 3302 Gulf Dr. Unit 201 Holmes Beach, Fl. 34217 Looking for luxury- you found it! Wow, what can you say about this gorgeous, custom direct Gulf front condo. The views you can take in from most parts of the top floor corner unit are breathtaking. Kitchen, living room, bedroom and of course the over-…
        • Shared outdoor pool (unheated)
        • 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

        Details

        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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        $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

        Details

        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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        $156

        3 BR / 3 BA / Sleeps 9

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        $156

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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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        $350

        6 BR / 4 BA / Sleeps 14

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        $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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        $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

        Details

        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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        $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

        Details

        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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        $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

        Details

        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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        $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

        Details

        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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        $100

        2 BR / 2 BA / Sleeps 6

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        $100

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        West Bay Cove 222

        2 BR / 2 BA / Sleeps 6 | Quick view

        Details

        West Bay Cove is a great location for taking advantage of everything that Anna Maria Island has to offer. Only a block from the public beach area, close to the grocery store, several shops and at a trolley stop, this condo will meet all of your needs without a car. The grounds are well cared for and you will feel …
        • Shared outdoor pool (unheated)
        • Internet Access
        • A/C or climate control
        • Balcony or terrace
        • Parking
        • Suitable for children - ask
        • Suitable for the elderly - ask

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        $180

        2 BR / 2 BA / Sleeps 4

        5 Reviews

        $180

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        ISLAND GIRL NORTH

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

        Details

        Reviews

        (5)

        Tropical, quiet, 2 bedroom/ 2 bath duplex, just over a block to the beach, and a block to the free Island trolley! Elevated, with one car garage underneath filled with beach chairs and wagon. Heated Pool surrounded by a large paver deck, lush landscape and plenty of seating. Sleeps up to 4. 1160 Sq. ft. Island …
        • Internet Access
        • Washing Machine
        • Clothes Dryer
        • Outdoor Dining Area
        • A/C or climate control
        • Suitable for children
        • Suitable for the elderly

        Details

        Reviews

        (5)

        A great location for both relaxing and having things to do!

        Left on Mar 01, 2014 for a stay in December 2013

        Our duplex was much more like a home than a room at the beach, and it was tastefully done with comfortable furniture. It's proximity to the beach was about perfect-- a short walk and you're there, without the noise and traffic of beachfront property. There are many interesting things to do and some fine restaurants nearby.

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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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        $124

        2 BR / 2 BA / Sleeps 6

        1 / 12

        $124

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        Coral Cottage

        2 BR / 2 BA / Sleeps 6 | Quick view

        Details

        Coral Cottage 6700 Holmes Blvd. Unit B (South Unit) Holmes Beach, Fl. 34217 This is a brand new renovation, ground level 2 bedroom, 2 bathroom bungalow which includes its own private heated pool nestled in lush tropical landscaping. It is only a short 2-3 minute stroll over to the pristine Anna Maria Gulf beach…
        • Heated Pool
        • High Speed Internet
        • Patio
        • Television
        • DVD Player
        • Suitable for children - ask
        • Suitable for the elderly - ask

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        $137

        2 BR / 2 BA / Sleeps 4

        1 / 16

        $137

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        Gulf Sands 102

        2 BR / 2 BA / Sleeps 4 | Quick view

        Details

        Gulf Sands #102 4200 Gulf Drive #102 Holmes Beach, FL 34217 This Gulf Sands, 2 bedroom 2 bathroom, second floor condo has been recently updated with new appliances and furnishings. Wonderful side views of the Gulf waters from the living room, master bedroom and private balcony. Large heated pool with nicely …
        • Shared outdoor pool (unheated)
        • Internet Access
        • Dishwasher
        • Suitable for children - ask
        • Suitable for the elderly - ask

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        $242

        2 BR / 2 BA / Sleeps 6

        16 Reviews

        $242

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        Gulf Front - Shady Pines

        2 BR / 2 BA / Sleeps 6 | Quick view
        “ Excellent ” 16 Reviews

        Details

        Reviews

        (16)

        SPECIAL - Nov. 07 -21, 2014 $200.00 / night + tax & cleaning (4 night minimum) Completely remodeled, 2 BR, 1-1/2 bath beach house right on the beautiful Gulf of Mexico. Walk out the door to a wide, white, powdery beach and the Gulf. This 2 bedroom beach house is located in the most perfect spot you willl …
        • Waterfront
        • Ocean or water views
        • Internet Access
        • Washing Machine
        • Clothes Dryer
        • Suitable for children
        • Suitable for the elderly
        • Wheelchair accessible - ask

        Details

        Reviews

        (16)

        Rita Stewart

        Left on Nov 13, 2010 for a stay in November 2010

        We recently spent 5 glorious days at Shady Pines, where our biggest decision was where to watch the sunset-from the family room where the whole beach side is glass, the adirondack chairs in the back yard at the edge of the sand, or 20 steps further at the edge of the water. This allows the sun to set right in front of the viewer. This house is absolutely wonderful-sooo clean, original art, and…

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        $135

        2 BR / 2 BA / Sleeps 6

        4 Reviews

        $135

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        Brigadoon

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

        Details

        Reviews

        (4)

        The Brigadoon, located at 504 70th Street in Holmes Beach is a wonderful home with a beautiful lagoon style heated pool. It's located on a quiet street in a lovely neighborhood and features a screened lanai and a BBQ area with gas grill. You'll want to wander around the yard and experience the fruit trees, tropical …
        • 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

        (4)

        Amazing stay

        Left on Jun 16, 2010 for a stay in June 2010

        Enjoyed, a most relaxing, guiet, and wonderful stay in this neat, clean home. Made happy memories in this lovely home.

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        $120

        2 BR / 2 BA / Sleeps 6

        1 Reviews

        $120

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        Bman Beach Cottage

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

        Details

        Reviews

        (1)

        The Bman Beach Cottage located at 2812 Avenue B in Holmes Beach is a cute 2 bedroom 2 bath private home. This ground level home has two screened lanais one overlooking the pool and Jacuzzi. The kitchen has been newly updated as well as one of the bathrooms. This property has long distance and WiFi included. There are …
        • 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

        (1)

        Everything you could want and only three blocks from a gorgeous Gulf beach!

        Left on Nov 06, 2014 for a stay in October 2014

        I stayed at the cottage for a little over two months. The owner has stocked the home with everything you could possibly want or need - comfortable, easy to care for, and the pool with built-in hot tub was fabulous! The pool is not heated but that wasn't an issue until late October. It was like borrowing a friend's home. If circumstances allow I would love to stay here again.

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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

        Details

        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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