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$68

2 BR / 1 BA / Sleeps 4

Sand Dollar Cottage-738NShore - Anna Maria vacation rentals
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Sand Dollar Cottage-738NShore

2 BR / 1 BA / Sleeps 4 | Quick view

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This Island holiday home with easy access to the Gulf of Mexico and colorful sunsets. Two bedroom and one bath vacation rental in a desirable north end of Anna Maria location. It is also just a flip-flop walk to the pristine gulf beaches. Pet friendly and wireless internet There are so many island activities you …
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$114

3 BR / 2 BA / Sleeps 7

2 Reviews

$114

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620 Rose Street

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

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Reviews

(2)

This lovely elevated vacation rental home features three bedrooms, two baths and a large living/dining room area for entertainment. The large screened lanai off the living room makes a pleasant place for morning coffee, evening meals or just sitting back, relaxing and reading. The lush enclosed garden below has …
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(2)

Wonderful Retreat

Left on Apr 28, 2009 for a stay in March 2009

This was such a relaxing expereince to be at this home. The screened porch just added so much to the home and we all loved it. The location was perfect and we were able to walk to restaurants and stores. It was very quiet and serence. The garden was lush and lovely. We hope to return next year.

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$100

3 BR / 2 BA / Sleeps 8

4 Reviews

$100

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Maple Cottage-120 Maple

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

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Reviews

(4)

Great ground level home on Maple Ave in Anna Maria CIty. West of Gulf Drive with no busy roads to cross. Three bedrooms and two baths. Extra bonus sun room off new deck perfect for a cookout. Kitchen is large enough to try your hand at island cusine, yet the Sandbar Restaurant is just up the street as well! …
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(4)

One of our best family vacations ever!

Left on Jul 24, 2008 for a stay in June 2008

We had a wonderful time during our vacation to AMI. One of the things that made our vacation so enjoyable was our unit. With 3BRs, a huge kitchen, top of the line decor and tons of living space the condo was definately top notch. The beach was absolutely beautiful and the trolley made getting around the island easy. We definately plan to return for another wonderful vacation next year. The Atwell…

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$124

2 BR / 2 BA / Sleeps 7

8 Reviews

$124

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Sea's the Day - 207 Coconut

2 BR / 2 BA / Sleeps 7 | Quick view
“ Excellent ” 8 Reviews

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Reviews

(8)

The various shades of blue throughout 207 Coconut might be a bit misleading since you'll feel anything but during your stay in it. But then again, this is the water lover's dream vacation cottage. You have the option of swimming in either natural or manmade beauty. The beach is located less than 100 steps away, but …
  • Shared outdoor pool (unheated)
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(8)

Vacation in Paradise

Left on Dec 03, 2009 for a stay in August 2009

Our family has vacationed on the west coast of Florida - Longboat Key and Anna Maria - for almost 30 years. Our stay at 207 Coconut was, by far, one of the best vacation experiences we have ever had. For one thing, Anna Maria is definitely the perfect beach destination, and Coconut fit our family's needs and expectations to a "T". We were thrilled at its location and ambiance and the pool was …

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$93

2 BR / 2 BA / Sleeps 6

The Seashell Cottage - Anna Maria vacation rentals
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$93

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The Seashell Cottage

2 BR / 2 BA / Sleeps 6 | Quick view

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Steps to the beach - "Old Florida" beach cottage located at 118 Palmetto Avenue, Anna Maria, Anna Maria Island, FL -- (2) Bed: (2 ) Bath: Accommodates up to (6) people: 1 King, 2 twins, 1 queen sleeper: Wireless : free long distance phone in the USA and enhanced cable channels. No smoking: Pets welcome Adorable two…
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$105

2 BR / 2 BA / Sleeps 6

Sea 'Esta - 890 North Shore - Anna Maria vacation rentals
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$105

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Sea 'Esta - 890 North Shore

2 BR / 2 BA / Sleeps 6 | Quick view

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Welcome to Sea 'Esta, located at 890 North Shore and enjoy this upscale designer home. Your beach access is a short stroll away and easy walk to the Rod N Reel Pier.Enjoy the feel of old Florida in this nicely furnished 2 bedroom 2 bath vacation rental get away. This is a desirable location is well sought after with …
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$129

2 BR / 2 BA / Sleeps 6

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$129

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Casa Nana

2 BR / 2 BA / Sleeps 6 | Quick view

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Enjoy an old fashioned Florida beach vacation at this wonderful cottage just 4 houses from the beach! One Florida family has spent over four decades building happy summer memories right in this spot, and they invite you to create some of your own treasured moments on your next visit to Anna Maria. Located right in …
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  • Patio
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$79

2 BR / 1 BA / Sleeps 6

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$79

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414 A Magnolia

2 BR / 1 BA / Sleeps 6 | Quick view

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This newly remodeled two bedroom duplex is situated halfway between the Gulf of Mexico and the Tampa Bay. Not more than 3 blocks in either direction. It is located on the north end of Anna Maria Island on Magnolia Avenue. The duplex is furnished with Tommy Bahama style furniture which offers a rich and comfortable …
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$68

2 BR / 1 BA / Sleeps 4

2 Reviews

$68

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316 Hardin A

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

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Reviews

(2)

This newly remodeled and updated island vacation rental duplex is just a stroll to the Gulf of Mexico and our beautiful sunsets. This home has been decorated to make you feel like you were in Key West. The living room offers an open floor plan to the kitchen to enjoy the family during your stay. The comfy …
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(2)

Outstanding furnishings and superb ventilation

Left on Apr 14, 2011 for a stay in March 2011

As a late arrvial, we had no personal interaction with Island Rental. Key pick-up works fine. Nice to be trusted.
The funishings far exceeded our fears/expectations. No cast-off furnishings. Screened in porch was favorite spot. Great cross ventilation. Kitchen worked very well and lacked nothing. Did purchase a good knife and cutting board (and a Keurig coffee maker.) Kudos for having …

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$114

3 BR / 2 BA / Sleeps 8

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North Shore Cottage-871 NShore

3 BR / 2 BA / Sleeps 8 | Quick view

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Welcome to 871 No Shore guest cottage. Enjoy the feel of "old Florida" with this charming split level 3 bedroom 2 bathroom accommodations located behind the main house. Great bayfront location with direct access to bay. Feel free to walk along the main house with easy access to the Bay beach on Tampa Bay. This …
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$121

1 BR / 1 BA / Sleeps 4

4 Reviews

$121

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Island Place Cottage: 1BR Pet-Friendly Cottage

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

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Reviews

(4)

This vacation rental is located on Anna Maria Island's historic Pine Avenue, halfway between the Gulf of Mexico and the Anna Maria City Pier! This adorable, one bedroom cottage, with high beamed ceilings, wood floors and shabby chic décor throughout is ideal for a vacation getaway! This quaint cottage offers a fully…
  • Internet Access
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  • Pet friendly
  • Suitable for children - over five
  • Suitable for the elderly

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(4)

Great cottage, great location.

Left on Jul 26, 2013 for a stay in July 2013

Cottage is perfectly located right in the heart of anna Maria. Quick walk to the Gulf beaches or to the Bay.

Cottage was immaculate and perfect size for the three of us. A few years ago we stayed in the adjacent Pineapple House which was also perfect for our larger party during that visit.

Would not hesitate to stay again.

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$124

2 BR / 2 BA / Sleeps 6

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Sunny Side Up

2 BR / 2 BA / Sleeps 6 | Quick view

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Sunny Side-Up 267 Gladiolus Street Anna Maria, Fl. 34216 Trendy colorful, happy cottage located in popular Anna Maria City. This 2 bedroom 2 bath ground level home was completely renovated inside and out. All new furniture throughout with lots of fun decor and an island feel. A delight the moment you enter …
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$111

1 BR / 1 BA / Sleeps 2

3 Reviews

$111

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SNAILS PACE

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

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Reviews

(3)

Great 1 Bedroom/1 Bath remodeled cottage on the quiet North End with outdoor patio, ceramic tile throughout, and granite countertops. The allure of the Gulf of Mexico Beach just 250 steps away. A back yard dock on Lake LaVista Bayou with a patio table, umbrella, and sling back chairs. Launch the provided kayaks right …
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  • Pet friendly
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(3)

It was perfectly amazing!

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

This cottage was exactly what my wife and I wanted for our honeymoon. It was super close to the beach and was definitely within walking distance of almost all of the restaurants and shops. We had such a wonderful time there and didn't want to leave after our week was over. The staff were very friendly and helpful, as were the locals that live in the area. They helped us with tips on where to eat …

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$125

3 BR / 2 BA / Sleeps 6

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$125

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Sunset Cottage On Rose

3 BR / 2 BA / Sleeps 6 | Quick view

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Sunset Cottage on Rose 710 Rose Street Anna Maria, FL 34216 Sunset Cottage on Rose is a beautiful newly renovated Island home located on the prestigious Northern End of Anna Maria Island! Tucked away on a quiet residential street this wonderful property is your home away from home. With just a short walk to the …
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    $128

    3 BR / 2 BA / Sleeps 8

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    $128

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    316 Hardin Ave

    3 BR / 2 BA / Sleeps 8 | Quick view

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    This newly remodeled and updated island vacation rental duplex is just a stroll to the Gulf of Mexico and our beautiful sunsets. This home has been decorated to make you feel like you were in Key West. This unique unit is actually two separate living spaces that adjoin in the center. Offering two separate full …
    • Shared outdoor pool (unheated)
    • Internet Access
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    $128

    2 BR / 2 BA / Sleeps 8

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    $128

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    North Bay Hideaway- 809 North Bay Blvd, Anna Maria

    2 BR / 2 BA / Sleeps 8 | Quick view

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    The best of both worlds on the Island is where the Gulf meets the Bay at the "Tip" of Island in Anna Maria. Beautiful Sunsets, Fishing Piers, a Park and Bird Watching can be found at the Northern tip of the Island. This 2BR/2BA plus a Loft is located one property from the beach access at Bean Point. Peeks of the Gulf …
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    • Wheelchair accessible - ask

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    $129

    2 BR / 1 BA / Sleeps 4

    2 Reviews

    $129

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    Light House: 2BR/1BA Canal-Front Home with Dock

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

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    Reviews

    (2)

    The Light House welcomes you in with its tropical landscaping, canal view and calming green exterior. This nicely furnished two-bedroom, one-bath vacation rental on Anna Maria Island has everything you need to begin a relaxing and restful vacation. Newer appliances will make quick work of breakfast or dinner, leaving…
    • Waterfront
    • Wireless Internet
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    • A/C or climate control
    • Suitable for children - over five
    • Suitable for the elderly

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    Reviews

    (2)

    Island Paradise

    Left on Jan 07, 2014 for a stay in December 2013

    One block from bay and four blocks from Gulf or Bean Point...what more could you want?!! Easy walk to all the restaurants and shopping on the North end of island (our favorite part of anna Maria). We brought our own bicycles and the garage was a good storage area for them.
    Loved the backyard view of the canal and the Florida room was excellent for dining in on those occassions.
    Cozy little …

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    $129

    3 BR / 2 BA / Sleeps 8

    1 Reviews

    $129

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

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

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    Reviews

    (1)

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

    (1)

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

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

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

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

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    $95

    2 BR / 1 BA / Sleeps 6

    1 Reviews

    $95

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    414 B Magnolia

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

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    Reviews

    (1)

    This newly remodeled two bedroom duplex is situated halfway between the Gulf of Mexico and the Tampa Bay. Not more than 3 blocks in either direction. It is located on the north end of Anna Maria Island on Magnolia Avenue. A new heated pool was just installed and only can be used by this unit. The home is furnished …
    • Shared outdoor pool (unheated)
    • Internet Access
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    • Suitable for children - ask
    • Suitable for the elderly - ask

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    Reviews

    (1)

    Neat duplex in an excellent location

    Left on Nov 25, 2014 for a stay in October 2014

    We usually book a house on Anna Maria a year in advance but this was a late booking, just for the two of us and we were not disappointed. The duplex was roomy, well equipped and the pool was an additional bonus. It's location was excellent, only a short walk to restaurants, shops and bars. And, more importantly to both piers which we love. We met the owner whilst we were there and he was a really…

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    $100

    1 BR / 1 BA / Sleeps 2

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    $100

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    Flamingo House: 1BR Elderly-Friendly Steps From Beach

    1 BR / 1 BA / Sleeps 2 | Quick view

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

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    $115

    2 BR / 1 BA / Sleeps 6

    1 Reviews

    $115

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    Southern Breeze 1

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

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    Reviews

    (1)

    Southern Breeze #1 607 Fern Street #1 Anna Maria, Fl. 34216 ISLAND 6-PLEX - Newly renovated top to bottom June 2013! These are 2 bedroom, 1 bath ground level units located at the tip of Anna Maria Island just steps from the Bay. Heated pool with nicely landscaped surroundings. Each is decorated with the feel of…
    • Shared outdoor pool (unheated)
    • Internet Access
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    Reviews

    (1)

    Descoberta Maravilhosa!!

    Left on Aug 21, 2014 for a stay in June 2014

    Amei conhecer a ilha Anna Maria! tanto que estou pretendendo voltar no próximo ano para passar pelo menos um mês inteiro! Alugamos essa casa pela internet com poucos dias de antecedência, recebemos um código por email que serviu para abir um cofre na entrada liberando as chaves da casa. Tudo estava limpo, arrumado, ar condicionado ligado (estava bem quente!). Dois quartos bem mobilhados, uma …

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    $125

    2 BR / 2 BA / Sleeps 6

    1 Reviews

    $125

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    Star Fish Cottage-209 Palm Ave

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

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    Reviews

    (1)

    When a starfish wants to get away, it's more than happy to just detach an arm and take time to recuperate. This elevated coastal cottage might be worth giving up an arm, but we can skip that part and just focus on you relaxing. Located just east of Gulf Drive, a scenic 200-yard walk will take you right to the sugar-…
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    (1)

    Perfect place to relax.

    Left on Jul 18, 2014 for a stay in May 2014

    I found the Star Fish Cottage in Anna Maria online and was enamored by the pictures and location. The cottage is all it promised to be and then some. A short walk to the beach, and close to local stores and restaurants. When I arrived the place was immaculate. Everything is there that you will need to enjoy a quiet, relaxing vacation. Just bring your clothes and personal items. Everything else…

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    $125

    2 BR / 1 BA / Sleeps 6

    10 Reviews

    $125

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    Becker's Beach Bungalow!

    2 BR / 1 BA / Sleeps 6 | Quick view
    “ Excellent ” 10 Reviews

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    Reviews

    (10)

    Charming, newly renovated, the Becker Beach Bungalow offers a comfortable stay less than 2 blocks from the beach. Accommodates 6 people comfortably; master bedroom with 1 queen bed, second bedroom with 2 twin beds, and an additional daybed with pop up in the sun room. The living room also has a queen size sofa bed. …
    • Wireless Internet
    • Housekeeping Optional
    • Washing Machine
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    • A/C or climate control
    • Suitable for children
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    • Wheelchair accessible

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    (10)

    Fabulous

    Left on Jun 29, 2011 for a stay in June 2011

    Becker's Beach Bungalow was a dream come true. So clean, comfortable and containing everything you would need made for a perfect vacation destination. The location is the best...right down the street from the beach, ice cream shop even closer and great restaurants and shops all around. Highly recommend this delightful "rental"...

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    $85

    2 BR / 2 BA / Sleeps 6

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    Villa Nora South

    2 BR / 2 BA / Sleeps 6 | Quick view

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    Only a block to the pristine white sands of our Gulf of Mexico beaches, this lovely two bedroom/two bath duplex is nestled at the end of a long shell driveway, and overlooks picturesque Lake LaVista, a body of water that began its life as a natural lake frequented by the island's early settlers. Sometime in the first…
    • Internet Access
    • A/C or climate control
    • Patio
    • Fitness Room
    • Satellite or cable TV
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $110

    2 BR / 1 BA / Sleeps 4

    7 Reviews

    $110

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    Waterfront, SeaView, Close to Beach & Restaurants

    2 BR / 1 BA / Sleeps 4 | Quick view
    “ Excellent ” 7 Reviews

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    Reviews

    (7)

    Seaside Views - Waterfront, Steps from Beach & Restaurants This water front, two bedroom condominium (ground floor), sits on the end of Pine Avenue, across the street from the beach and has wonderful seaside views of the bay. It also has it's own private fishing dock and boat slip! We have tastefully furnished …
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      (7)

      This place is perfect!

      Left on Jul 14, 2009 for a stay in January 2008

      Anna Maria is quaint and relaxing. The location of this condo made it even more so. It's nice to enjoy a comfortable condo in a great location. Hope to do it again.

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      $122

      2 BR / 1 BA / Sleeps 5

      1 / 14

      $122

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      Pine Ave and North Shore Drive Anna Maria Villa A

      2 BR / 1 BA / Sleeps 5 | Quick view

      Details

      This villa is quaint and adorable tucked in a quiet neighborhood just 9 houses from the Gulf of Mexico and white sandy north end Anna Maria Island beaches. Step outside your door and stroll down the street in 1 minute or less to the quaint shops and cafes along Pine Ave. Walk to everything the north end has to offer…
      • Internet Access
      • Washing Machine
      • Clothes Dryer
      • Outdoor Dining Area
      • A/C or climate control
      • Pet friendly
      • Suitable for children
      • Suitable for the elderly
      • Wheelchair accessible

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