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$157

2 BR / 1 BA / Sleeps 6

3 Reviews

$157

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Escape to Serenity A: 2BR Pet-Friendly Pool Home

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

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Reviews

(3)

Escape to Serenity sums it up for this quaint and cozy duplex (with no shared walls). You will feel as if you have landed on your own personal island with this gem of a property. This fantastic, two-bedroom, one-bathroom vacation rental will help you find some serenity. This home boasts an all-new kitchen, featuring …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children - over five
  • Suitable for the elderly

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(3)

Everything we wanted!

Left on Jun 24, 2014 for a stay in June 2014

Great location, beautiful amentities and much appreciated attention to detail. Very clean and is a block from the beach!

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$200

2 BR / 2 BA / Sleeps 5

1 Reviews

$200

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Citrus Cottage

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

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Reviews

(1)

Welcome to the Citrus Cottage on Anna Maria Island. This completely remodeled duplex is comprised of two stunning new beach homes that are close to the beach and in a quiet residential neighborhood. However, until Labor Day 2014 we are offering a 10% discount on this property because of new construction that will …
  • Internet Access
  • Parking
  • Grill
  • Stereo or CD player
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

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Reviews

(1)

Paradise Found

Left on Nov 19, 2014 for a stay in November 2014

Brand new five-star cottage with luxury sheets, fluffy towels, great dishes, warm swimming pool, big TV, snuggly blankets for watching big TV, and light fresh decor. The cottage is also situated in a great location - walking distance to the beach, and a short bike ride to Pine Avenue.

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$90

2 BR / 2 BA / Sleeps 6

3 Reviews

$90

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Cove at Sandy Pointe 202A

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

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Reviews

(3)

The Cove at Sandy Pointe #202, at 3601 East Bay Drive is a cheerful, two bedroom and two bath condo in a secluded complex close to shopping and conveniently located to the beach. Sandy Point features undercover parking and a large heated pool. Each unit has a large screened lanai.This well appointed and recently …
  • Shared outdoor pool (unheated)
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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Reviews

(3)

Most relaxing vacation

Left on Aug 19, 2011 for a stay in July 2011

I was extremely pleased with the setup of the rental from the beginning. The pictures did not do this condo justice. It was much larger and spacious than I had thought. The pool was no more than 25 feet from where we parked out car... The beach was within walking distance, but with all the stuff we brought we drove to make it easier. It was conveniently located within walking distance to Publix, …

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$184

2 BR / 2 BA / Sleeps 6

LAZY DAZE - Holmes Beach vacation rentals
1 / 29

$184

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LAZY DAZE

2 BR / 2 BA / Sleeps 6 | Quick view

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Great 2 Bedroom/2 Bath Home with a private Heated Pool, located on a quiet street west of Gulf Drive, just 3 houses to the beach!! King sized master bedroom with TV/DVD, Twins in guest room with TV/DVD, and sleeper sofa in living room! Cable TV/DVD and Wii Console in living Room, High speed Internet TV in Dining Room…
  • 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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$137

2 BR / 2 BA / Sleeps 4

Gulf Sands 102 - Holmes Beach vacation rentals
1 / 16

$137

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Gulf Sands 102

2 BR / 2 BA / Sleeps 4 | Quick view

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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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$125

3 BR / 2 BA / Sleeps 6

Peacock Crossing - Holmes Beach vacation rentals
1 / 19

$125

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Peacock Crossing

3 BR / 2 BA / Sleeps 6 | Quick view

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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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    $90

    2 BR / 1 BA / Sleeps 6

    1 / 20

    $90

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    Anna Maria Island--Two Month Min.--Gorgeous!

    2 BR / 1 BA / Sleeps 6 | Quick view

    Details

    This newly decorated and refurbished condo is the answer to your dreams this fall. This 2 bedroom 1.5 bath condo is 300 steps to the beautiful white sands and crystal blue waters of Anna Maria Island. The condo is completely turn-key ready--nothing to bring but your swimsuit and toothbrush. Condo has 2 large bedrooms…
    • Suitable for children
    • Suitable for the elderly

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    $514

    6 BR / 4 BA / Sleeps 14

    1 / 40

    $514

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    MARGARITA-VILLE

    6 BR / 4 BA / Sleeps 14 | Quick view

    Details

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

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    $200

    1 BR / 1 BA / Sleeps 4

    1 / 15

    $200

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    Coconuts Beach Front Unit 110 Upstairs

    1 BR / 1 BA / Sleeps 4 | Quick view

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    One bedroom one bath condo located on the beach. The Coconuts Beach Resort is a beach front property in Holmes Beach on Anna Maria Island. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 4. There are two double beds in the bedroom …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Housekeeping Optional
    • Washing Machine
    • Smoking allowed - ask
    • Suitable for children
    • Suitable for the elderly

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    $350

    3 BR / 2 BA / Sleeps 8

    8 Reviews

    $350

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    Palm Gables 110

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

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    Reviews

    (8)

    Palm Gables Condominium located at 110 36th Street in Holmes Beach is one of the most sought after Holmes Beach rental complexes. It’s in a popular, quiet area of Holmes Beach yet it’s close to shopping and restaurants. Palm Gables is a small 7 unit complex and features secured undercover parking and an elevator…
    • 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

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    Reviews

    (8)

    Great view

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

    OK, but not nearly as nice as PG 106

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    $125

    2 BR / 2 BA / Sleeps 4

    1 / 9

    $125

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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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    $236

    3 BR / 2 BA / Sleeps 8

    2 Reviews

    $236

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    CHIKI TIKI WEST

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

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    Reviews

    (2)

    Beautiful Tropical villa with Bamboo ceilings and furniture, a private landscaped backyard, Heated pool, gas grill, and a large covered tiki bar, paver deck, and Full kitchen with Granite countertops and Stainless Steel appliances. Sleeps up to 8 people. 1316 Sq. ft. 303A 64th St., Holmes Beach Three Bedroom/Two …
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • A/C or climate control
    • Central heating
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (2)

    Great place to stay for our first visit to America

    Left on Aug 09, 2013 for a stay in January 2013

    We were blown away by the location. Only a few minutes walk to the most beautiful white sandy beach, just one street back from the sea front Great wildlife, dolphins, pelicans, so much to see. The house was well equipped with everything you need. Air conditioning of course, fans, lovely bathrooms. Great sea water pool in a lovely courtyard garden. Within walking distance of shops and some…

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    $100

    2 BR / 3 BA / Sleeps 8

    9 Reviews

    $100

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    Bollinger Duplex, A

    2 BR / 3 BA / Sleeps 8 | Quick view
    “ Very Good ” 9 Reviews

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    Reviews

    (9)

    The Bollinger Duplex, side A is a very comfortably furnished and spacious duplex apartment located at 6909 Gulf Drive in the preferred, quiet area of northern Holmes Beach. This property is located about one-half block to beautiful Gulf of Mexico where you can walk for miles in either direction on the white, sandy …
    • Internet Access
    • Grill
    • Pet friendly
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (9)

    Close to the Beautiful Gulf

    Left on May 28, 2009 for a stay in May 2009

    The duplex we rented was spacious and very comfortable and was just a very short walk from the Gulf of Mexico. I did have a few issues, though. We came in expecting to have available to us for our use things like paper towels, toilet paper, garbage bags, and plastic containers in which we could store leftovers after meals. None of these items were available and had to be purchased by us after we …

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    $230

    3 BR / 2 BA / Sleeps 6

    35 Reviews

    $230

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    Captains Quarters

    3 BR / 2 BA / Sleeps 6 | Quick view
    “ Excellent ” 35 Reviews

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    Reviews

    (35)

    The Captain's Quarters, located at 2801 Gulf Drive in Holmes Beach is an extremely popular three bedroom, two bath home with a private heated salt water pool, tropical landscaping, a double car garage and gulf views from the open deck. This wonderful beach house is less than a five-minute stroll to the beach. The …
    • 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

    (35)

    4 Years and Counting at Captains Quarters

    Left on Feb 23, 2009 for a stay in February 2009

    This is our fourth year staying at Captain's Quarters. We love the house, the location and the rental company is extremely nice. The upkeep of the house is excellent and we always feel like we are at home! We look foward to our fifth year there.

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    $189

    2 BR / 2 BA / Sleeps 4

    1 Reviews

    $189

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    Bluefin Cottage

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

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    Reviews

    (1)

    Welcome to Bluefin Cottage on Anna Maria Island. This completely remodeled duplex is comprised of two stunning new beach homes that are close to the beach and in a quiet residential neighborhood. The Bluefin Cottage side includes a private heated pool (not shared), hot/cold outdoor shower, lush landscaping …
    • Internet Access
    • Parking
    • Grill
    • Stereo or CD player
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask

    Details

    Reviews

    (1)

    All rentals will be compared to Bluefin cottage.

    Left on Feb 06, 2015 for a stay in January 2015

    Bill and I arrived at Bluefin Jan 10 for 2 weeks. I have never rented a more beautiful clean accomodation ever. We loved it so much we would have moved it to BC if possible.Everything was built to the highest standard. I am sorry I never met Karen but Ben took such good care of us responding to any question or wish we had. The pool surround of brick made it difficult for me to enter but a bar …

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    $150

    2 BR / 2 BA / Sleeps 6

    1 Reviews

    $150

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    Calm Horizon unit D gorgeous pool,steps to beach

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

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    Reviews

    (1)

    Gorgeous gulf views and steps to white sandy beaches across the street from this 2 bedroom,2 bath elevated vacation rental. Up two flights of stairs to this top unit, with a partial view of the Gulf of Mexico just outside your front door. With 12 x 63 open covered deck below to enjoy the gulf sunsets. Feel the warm…
    • Ocean or water views
    • Shared outdoor pool (unheated)
    • Wireless Internet
    • Housekeeping Optional
    • Washing Machine
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly - ask

    Details

    Reviews

    (1)

    Ok

    Left on Jan 07, 2015 for a stay in December 2014

    The location of this rental was wonderful,just a few steps from one of the most Beautiful Beaches,we rented this for 31 day's, on the down side, it needs to be up dated,the carpet was stained,the comforter on the King bed needs to be replaced, I had too wash the comforter on the queen bed,because it smelled,other wise everything was clean,we did not have access to the garage or our back deck,our …

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    $106

    1 BR / 1 BA / Sleeps 4

    11 Reviews

    $106

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    Islands West Resort 6

    1 BR / 1 BA / Sleeps 4 | Quick view
    “ Excellent ” 11 Reviews

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    Reviews

    (11)

    Islands West Resort, located at 3605 Gulf Drive in Holmes Beach, is a tranquil resort with a large heated pool just a short stroll to the Gulf, shopping and restaurants. Enjoy the relaxing charm of island living when you stay at the Islands West Resort. The property consists of four, one bedroom suites, a two bedroom…
    • 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

    (11)

    Cute and Comfortable

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

    My husband and I have stayed on Anna Maria Island several times and just love it there. This trip, I was going by myself for some quiet time. I really enjoyed staying at Islands West. The pool was warm and inviting and my unit was clean and decorated nicely. I would definitely stay there again.

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    $165

    2 BR / 2 BA / Sleeps 6

    5 Reviews

    $165

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    Pool Party South side

    2 BR / 2 BA / Sleeps 6 | Quick view
    “ Very Good ” 5 Reviews

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    Reviews

    (5)

    The Pool Party South side, located at 6102 Marina Drive in Holmes Beach, is a beautiful two bedroom, two bath duplex with a pool area that is unsurpassed! This unit features a heated pool with a spa surrounded by mature, native plantings as well as a shaded hammock and an outdoor bar with charcoal grill and sink. The …
    • 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

    (5)

    Better than the north side

    Left on Feb 23, 2009 for a stay in February 2009

    We were all pleased by the Pool Party South side and by the team of Island Vacation Properties.
    It was the 4th year I used your services, every time with different guests, and it was again a pleasure.
    I like this villa because of the pool and the spa. The limitation with the pool heater only available for the spa was understandable but a bit disappointing since it's called the Pool Party for a …

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    $250

    3 BR / 2 BA / Sleeps 6

    1 / 24

    $250

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    Coastal Sunset

    3 BR / 2 BA / Sleeps 6 | Quick view

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    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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    $107

    2 BR / 1 BA / Sleeps 4

    2 Reviews

    $107

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    New Heron: 2BR "Perfect Spot" a Block from Beach

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

    Details

    Reviews

    (2)

    Just one short block away from the pristine water of the Gulf of Mexico and Anna Maria Island's gleaming white sand beaches, this two-bedroom, one-bath vacation rental has been completely remodeled inside and out for your vacationing pleasure. A well-appointed kitchen and outdoor grill may entice you to create a few …
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • A/C or climate control
    • Porch
    • Pet friendly
    • Suitable for children - over five
    • Suitable for the elderly

    Details

    Reviews

    (2)

    Loud

    Left on Apr 10, 2013 for a stay in March 2013

    If you are looking for a peaceful rental where you hear birds singing and pretty smelling Island flowers this is NOT the place. This rental is located right on busy Gulf Drive right across the street from a major construction site. Our stay consisted of heavy noise pollution both from cars and from a 5 house construction site that began every morning at 8am-hammering, cement mixers, diesel …

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    $250

    3 BR / 3 BA / Sleeps 6

    7 Reviews

    $250

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    Villa de la Playa

    3 BR / 3 BA / Sleeps 6 | Quick view
    “ Excellent ” 7 Reviews

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    Reviews

    (7)

    Villa de la Playa is a luxurious three bedroom, three bath town home with a private pool and spa, located at 3603 4th Avenue in Holmes Beach, less than a block to the white sandy beach. It is a top of the line Anna Maria vacation rental!This totally renovated property left nothing undone! A new gourmet kitchen with …
    • 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

    (7)

    Would Definately Go Back

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

    My wife and I went to Anna Maria, FL to get married. We stayed at the Villa de la Playa and LOVED IT! The pool and hot tub were very well maintained and extremely relaxing. The owners had everything we could have needed and more. They had pool toys, blenders, games, etc... This was a beautiful property and very close to the Ocean (2 minute walk). Check out Skinny's Bar if you stay at this …

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    $121

    2 BR / 2 BA / Sleeps 4

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    $121

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    Sun-Day West: 2BR Family- & Pet-Friendly near Beach

    2 BR / 2 BA / Sleeps 4 | Quick view

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    Sun-Day West is the picture-perfect name for this two-bedroom, two-bath, elevated duplex. Located in Holmes Beach on Anna Maria Island, this vacation rental features a large, west-facing balcony that allows for plenty of sunshine in the afternoon and shade in the morning for that early cup of coffee before heading …
    • Wireless Internet
    • Washing Machine
    • Clothes Dryer
    • A/C or climate control
    • Balcony or terrace
    • Suitable for children - over five
    • 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

    Details

    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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    $100

    2 BR / 2 BA / Sleeps 4

    3 Reviews

    $100

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    Fountainhead Condo 4

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

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    Reviews

    (3)

    Fountainhead Condo #4, located at 3402 6th Avenue in Holmes Beach is just a few steps from the beautiful beaches and emerald green water of the Gulf. This eight unit complex has a heated pool and laundry room on site.This unit is beautifully furnished and well equipped for your enjoyment. The unit itself offers every …
    • Shared outdoor pool (unheated)
    • Internet Access
    • Grill
    • Pet friendly - ask
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (3)

    2009 Murphy's Vacation - Fountainhead #4

    Left on Oct 23, 2009 for a stay in October 2009

    We had an excellent time. The condo was very spacious and well equipment for all our needs. The pool area was very clean and a great place to relax. The beach was awesome. I could not believe how warm the ocean was. All the services that we required were in the immediate area, ie: Groceries, Liquor, Golf, Shopping, etc.

    We will recommend this condo to our family and friends.

    Tell the …

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    $120

    1 BR / 1 BA / Sleeps 2

    1 Reviews

    $120

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    Villas on Anna Maria Island one bedroom one bath

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

    Details

    Reviews

    (1)

    This lovely property features a tropical setting surrounding a heated swimming pool. The six unit complex is located one block from the beach. Great for family reunions or wedding parties. This unit is a one bedroom one bath full size apartment. King bed in bedroom and a sofa sleeper in the living room.
    • Internet Access
    • Housekeeping Optional
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (1)

    Nice Quiet Place

    Left on Feb 03, 2015 for a stay in January 2015

    The pictures are pretty spot on. There are a total of six units in the complex. If you are looking for nightlife and a wild time, this is not the place for you. It's very quiet and relaxing and the other people there were very nice. Joyce the manager was very helpful if we needed anything. The bed is a king and very comfortable. Lots of great places to eat on the island. We did a lot of cooking …

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    $211

    4 BR / 2 BA / Sleeps 10

    1 Reviews

    $211

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    4 Bedroom w/ Lagoon pool/spa & golf cart- comes w/ all the Toys!

    4 BR / 2 BA / Sleeps 10 | Quick view
    “ Very Good ” 1 Reviews

    Details

    Reviews

    (1)

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

    Details

    Reviews

    (1)

    Great vacation home with pool!

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

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

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    $189

    2 BR / 2 BA / Sleeps 6

    3 Reviews

    $189

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    SUN DAZE

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

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    Reviews

    (3)

    Adorable and Updated 2 BR/2BA villa with a private heated pool. This villa is located on a quiet residential street, just a short walk to the beautiful beach, with no busy streets to cross to get there, and easily walkable to the 'downtown' Holmes Beach area for shopping and restaurants and more! Features include …
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • A/C or climate control
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (3)

    Would totally stay here again!

    Left on Jul 24, 2014 for a stay in July 2014

    This home was nicely furnished, clean, and in a great location. It was a short walk (4-5 minutes pulling a wagon and walking with kids) to the beach. We had no busy streets to cross- just down a block and a half. The street was quiet. The pool was beautiful as were the upgrades in the home. We could sometimes hear the sound of the television from the other unit (126A) through the walls, but we …

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    $158

    3 BR / 2 BA / Sleeps 8

    1 / 14

    $158

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    North Beach Village 233

    3 BR / 2 BA / Sleeps 8 | Quick view

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    Newly decorated 3 bedroom, 2 bath townhouse located in central Holmes Beach just a half block from the beach. Sleeps up to 8 people. Amenities Include: Full kitchen, dishes, cook ware, utensils, dishwasher, microwave, blender, toaster, coffee maker, linens, washer/dryer, central air conditioning/heat, cable TV, VCR/…
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly - ask

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    $145

    2 BR / 2 BA / Sleeps 6

    1 / 11

    $145

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    Sandy Pointe 110 Gorgeous unit, small pet friendly

    2 BR / 2 BA / Sleeps 6 | Quick view

    Details

    Very spacious two bedroom Condo with a large living room. Flat Screen TV, fully equipped kitchen with all the appliances. Not far from the beach, and short distance to area shopping. Unit has heated pool, and a relaxing Pool deck area. Main bedroom has a King size bed with a private bathroom and Second bedroom has as …
    • Internet Access
    • Housekeeping Optional
    • Washing Machine
    • Clothes Dryer
    • A/C or climate control
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly - ask

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    $200

    2 BR / 2 BA / Sleeps 4

    1 / 12

    $200

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    Castaway Cottage

    2 BR / 2 BA / Sleeps 4 | Quick view

    Details

    Welcome to Castaway Cottage on Anna Maria Island. This completely remodeled duplex is comprised of two stunning new beach homes that are close to the beach and in a quiet residential neighborhood. The Castaway Cottage side includes a private heated pool (not shared), hot/cold outdoor shower, lush landscaping …
    • Internet Access
    • Parking
    • Grill
    • Stereo or CD player
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $236

    3 BR / 2 BA / Sleeps 6

    1 / 32

    $236

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    SERENDIPITY

    3 BR / 2 BA / Sleeps 6 | Quick view

    Details

    Gorgeous 3 bedroom/2 bath villa, with Private Heated Pool and Large Tiki Bar. Newly remodeled with granite countertops, stainless appliances, and brand new furnishings throughout. Outdoor paver patio for private sunning, or put the umbrella and chairs in the pool to cool off. The beach is only a block away, and …
    • Shared outdoor pool (unheated)
    • A/C or climate control
    • Parking
    • Grill
    • Satellite or cable TV
    • Suitable for children
    • Suitable for the elderly

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    $154

    2 BR / 2 BA / Sleeps 6

    1 / 23

    $154

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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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    $244

    3 BR / 2 BA / Sleeps 8

    1 / 18

    $244

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    BLUESKY

    3 BR / 2 BA / Sleeps 8 | Quick view

    Details

    Beautiful, Brand New, 3 bedroom/2 bath home with Heated Pool and Hot Tub! Granite Countertops, vaulted ceilings, Stainless Appliances, and more. Great location in a quiet neighborhood, just a couple blocks to the beach, and a half block to the Free Island trolley. Enjoy the pool and hot tub with the outside flat …
    • Hot Tub/Jacuzzi
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Suitable for children
    • Suitable for the elderly

    PreviousNext property

    $154

    2 BR / 2 BA / Sleeps 6

    1 / 27

    $154

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    CASA SIERRA 205A

    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

    PreviousNext property

    $133

    2 BR / 3 BA / Sleeps 4

    1 / 16

    $133

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    Bay Bella Vista

    2 BR / 3 BA / Sleeps 4 | Quick view

    Details

    Bay Bella Vista 244 S. Harbor Drive Unit 2 Holmes Beach, Fl 34217 BAYFRONT CONDO - This 2 bedroom, 3 bathroom condo is beautifully furnished and features exceptional views of the intracoastal waterway. Enjoy the breathtaking views from the Master bedroom and living room! There is a private rooftop sundeck and …
    • Shared outdoor pool (unheated)
    • Dishwasher
    • Suitable for children - ask
    • Suitable for the elderly - ask

    PreviousNext property

    $90

    2 BR / 2 BA / Sleeps 6

    2 Reviews

    $90

    Inquire

    Cove at Sandy Pointe 113

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

    Details

    Reviews

    (2)

    The Cove at Sandy Pointe #113, at 3601 East Bay Drive is a cheerful, two bedroom and two bath condo in a secluded complex close to shopping and conveniently located to the beach. Sandy Pointe features undercover parking and a large heated pool. Each unit has a large screened lanai.This well appointed and recently …
    • 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)

    Pleasant relaxing week on anna Maria Island, FL.

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

    Good value. Comfortable roomy condo on a unique island location.Laid back friendly atmosphere.

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    $143

    2 BR / 1 BA / Sleeps 4

    1 / 14

    $143

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    Kims Kottage East

    2 BR / 1 BA / Sleeps 4 | Quick view

    Details

    Kim's Kottages East 205E 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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    $190

    2 BR / 2 BA / Sleeps 6

    1 Reviews

    $190

    Inquire

    Island Bay House Up

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

    Details

    Reviews

    (1)

    The Island Bay House upstairs unit is a glorious two bedroom two bathroom bay front duplex located at 232 South Harbor Drive in Holmes Beach. This spacious duplex features an elevator, boat dock, heated indoor pool and spa. This property features spectacular panoramic views of the Intracoastal and Tampa Bay from …
    • Waterfront
    • 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

    (1)

    Great Bayside View

    Left on Mar 06, 2014 for a stay in February 2014

    Loved the spaciousness of the unit and the gorgeous view. Unit accommodated two couples fairly well although it is ideally set up for a family situation; twin beds in one room with a small guest bathroom. Master bedroom/bath was large, as was the kitchen. Unit well stocked with kitchen supplies but, linens were a little tired. It was nice to have a washer/dryer in the unit and when I called …

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    $180

    2 BR / 2 BA / Sleeps 4

    5 Reviews

    $180

    Inquire

    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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    $120

    2 BR / 2 BA / Sleeps 4

    1 / 27

    $120

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    SEABREEZE D

    2 BR / 2 BA / Sleeps 4 | Quick view

    Details

    Two bedroom, two bath condo in the quiet, four-unit complex of Seabreeze! Clean and Comfortable! Nicely appointed kitchen with Stainless Steel Applicances. Conveniently located for shopping, restaurants, and the beach, yet tucked back into a quiet area! Just a block to Skinny's for the Best Burger on Anna Maria Island…
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • A/C or climate control
    • Suitable for children
    • Suitable for the elderly

    PreviousNext property

    $90

    2 BR / 2 BA / Sleeps 6

    4 Reviews

    $90

    Inquire

    Cove at Sandy Pointe 208A

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

    Details

    Reviews

    (4)

    The Cove at Sandy Pointe #208, at 3601 East Bay Drive is a cheerful, two bedroom and two bath condo in a secluded complex close to shopping and conveniently located to the beach. Sandy Pointe features undercover parking and a large heated pool. Each unit has a large screened lanai.This well appointed and recently …
    • 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

    (4)

    Great vacation

    Left on Apr 01, 2009 for a stay in March 2009

    We thoroughly enjoyed our stay! We needed to get away for a quiet vacation and this setting provided just what we needed. We would gladly return!

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    $165

    1 BR / 2 BA / Sleeps 4

    1 / 15

    $165

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    Coconuts Poolside Unit 102

    1 BR / 2 BA / Sleeps 4 | Quick view

    Details

    One bedroom one bath condo located on the poolside. The Coconuts Beach Resort is a beach front property in Holmes Beach on Anna Maria Island. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 4. There are two double beds in the …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • A/C or climate control
    • Smoking allowed - ask
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible

    PreviousNext property

    $95

    1 BR / 1 BA / Sleeps 6

    6 Reviews

    $95

    Inquire

    Anna Cabana Bungalow #2

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

    Details

    Reviews

    (6)

    Anna Cabana Bungalow #2 located at 3711 4th Avenue in Holmes Beach is in a ground level five unit complex that’s fun and affordable. It adjoins three other of the Cabana Bungalow units and is next door to the Cabana Beach House. With the numerous room configurations this is a perfect complex for larger families who …
    • 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

    (6)

    I love Florida

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

    This is a casual comfortable unit about a block from the gulf. It is decorated in bright cheerful colors and the furniture is comfortable. Bring your own beach towels, there is a pay washer/drier to share in front. I prefer the unit to a motel because you can cook some meals to save money and you have more room then a motel or hotel. The kitchen is small but who will be preparing elaborate …

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    $175

    2 BR / 1 BA / Sleeps 5

    1 Reviews

    $175

    Inquire

    Starfish Shack

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

    Details

    Reviews

    (1)

    Welcome to the Starfish Shack on Anna Maria Island. This completely remodeled duplex is comprised of two stunning new beach homes that are close to the beach and in a quiet residential neighborhood. The Starfish Shack side includes a private heated pool (not shared), hot/cold outdoor shower, lush landscaping …
    • Internet Access
    • Parking
    • Grill
    • Stereo or CD player
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask

    Details

    Reviews

    (1)

    Absolutely "ticketyboo"

    Left on Sep 22, 2014 for a stay in September 2014

    The use of the mobile app prior to attending was a godsend, very useful and informative. The apartment was spotless and fulfilled our needs exactly. The description was wholly accurate, and exceeded our expectations. Make use of all the amenities, outside shower, the lovely warm pool, the nearby beach and equipment. The free use the regular trolley bus to the pier and shops was great, local …

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    $236

    4 BR / 3 BA / Sleeps 10

    6 Reviews

    $236

    Inquire

    Beautiful Villa by the Sea: 4BR Pet-Friendly Pool Home

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

    Details

    Reviews

    (6)

    This four-bedroom pet-friendly vacation rental with a heated pool is just a block to the white sand beaches of Anna Maria Island and the Gulf of Mexico. Located in Holmes Beach, Beautiful Villa by the Sea offers an open floor plan with plenty of space to accommodate 10. On the main floor you will find the living room…
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • A/C or climate control
    • Patio
    • Pet friendly
    • Suitable for children - over five
    • Suitable for the elderly - ask

    Details

    Reviews

    (6)

    Well kept home

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

    Beautiful Villa By The Sea was the ideal place for our family vacation. we love anna Maria, and this house met all our needs. It is clean, neat, and organized. The only complaint is that the bed in the upstairs bedroom (smaller room) was very hard and creaky and hard to sleep in. A new set of mattress/boxspring would be worth the investment for your guests' comfort.

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    $120

    2 BR / 2 BA / Sleeps 4

    4 Reviews

    $120

    Inquire

    Sunbow Bay 308

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

    Details

    Reviews

    (4)

    Sunbow Bay Condominium #308 located at 3805 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, on site laundry room …
    • Waterfront
    • Ocean or water views
    • 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)

    Vacation rental

    Left on Jun 03, 2009 for a stay in May 2009

    We have been coming to this condo for over six years. We have enjoyed our time until recently. Upon arrival we found out they were selling the condo we were staying in. We didn't realize they could call at a moments notice to show the place or not even let you know they were coming. This was unsettling to say the least. We had to worry about people coming in and out even when you weren't there. …

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    $175

    2 BR / 1 BA / Sleeps 5

    1 / 13

    $175

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    Seahorse Beach House

    2 BR / 1 BA / Sleeps 5 | Quick view

    Details

    Welcome to the Seahorse Beach House on Anna Maria Island. This completely remodeled duplex is comprised of two stunning new beach homes that are close to the beach and in a quiet residential neighborhood. The Seahorse Beach House side includes a private heated pool (not shared), hot/cold outdoor shower, lush …
    • Internet Access
    • Parking
    • Grill
    • Stereo or CD player
    • Suitable for children - ask
    • Suitable for the elderly - ask

    PreviousNext property

    $171

    2 BR / 2 BA / Sleeps 6

    2 Reviews

    $171

    Inquire

    Sunset Beach: 2BR Family-Friendly Condo near Beach

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

    Details

    Reviews

    (2)

    Kick off your shoes, sit back, relax, and enjoy a view of the sparkling waters of the Gulf of Mexico and the white sand beaches of Anna Maria Island from the balcony of this two-bedroom, two-bath condo. This lovely, beachfront condo has been newly decorated with a unique kind of "Florida-style" furnishings from the …
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • A/C or climate control
    • Suitable for children - over five
    • Suitable for the elderly - ask

    Details

    Reviews

    (2)

    lovely condo

    Left on Mar 12, 2014 for a stay in February 2014

    we thoroughly enjoyed staying our stay in unit 102. it was decorated very tastefully and fully equipped. far enough back from the beach to be peaceful but still only steps away. the stores were only a short walk away and the trolley was a great way to get to the restaurants and stopped right outside our door. the only thing missing might be a bbq for the nights you want to eat in.

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    $157

    2 BR / 1 BA / Sleeps 6

    4 Reviews

    $157

    Inquire

    Escape to Serenity B: 2BR Pet-Friendly Pool Home

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

    Details

    Reviews

    (4)

    Escape to Serenity sums it up for this quaint and cozy duplex (with no shared walls). You will feel as if you have landed on your own personal island with this gem of a property. This fantastic, two-bedroom, one-bathroom vacation rental will help you find some serenity. This home boasts an all-new kitchen, featuring …
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • A/C or climate control
    • Suitable for children - over five
    • Suitable for the elderly

    Details

    Reviews

    (4)

    Cozy, Comfortable and Clean!

    Left on Mar 14, 2014 for a stay in March 2014

    We really loved this colorful duplex! It was clean and comfortable. We had everything we needed. A nice perk was having our own pool! The trolley stop was nearby. Quick walk to the beach. Our only suggestion would be to have a fan in the bathroom. Other than that, absolutely no complaints. We would love to come back here again!

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    $124

    2 BR / 2 BA / Sleeps 4

    1 / 9

    $124

    Inquire

    Island Beach Club 1

    2 BR / 2 BA / Sleeps 4 | Quick view

    Details

    Island Beach Club #1 3013 Avenue F #1 Holmes Beach, FL 34217 The Island Beach Club #1 is a newly updated ground level condo which is tucked away in the quiet Gulf front community. This 2 bedroom and 2 bathroom home has all new tile floors, fully equipped kitchen and much more as part of its renovation. Right off …
    • Shared outdoor pool (unheated)
    • Internet Access
    • Dishwasher
    • Suitable for children - ask
    • Suitable for the elderly - ask
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