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Cottages in Anna Maria Island, FL

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    All 899 Rentals in Anna Maria Island
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    Travellers to Anna Maria Island are booking June dates now. Secure your holiday rental today, and have the perfect trip.
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    $96
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    1 / 19
    4 of 5 stars (3) Very good
    Holmes Beach
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Reviews (3) Make Enquiry
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    $127
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    1 / 17
    4.5 of 5 stars (2) Very good
    Holmes Beach
    2 Bedrooms / 7 Bathrooms / Sleeps 7
    Overview Reviews (2) Make Enquiry
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    $245
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    1 / 31
    4.5 of 5 stars (7) Very good
    Anna Maria
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    $1,070
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    1 / 22
    4.5 of 5 stars (7) Very good
    Bradenton Beach
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (7) Make Enquiry
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    • Internet Access
    • Shared Outdoor Pool...
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
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    • Elder access
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    About this property
    Bridgeport Condo 101, located at 501 Gulf Drive North in Bradenton Beach is a spacious two bedroom, two-bath condo with an elevator, undercover parking and large heated pool. You can enjoy Gulf views from virtually every room. Bridgeport Condo is a great Bradenton Beach rental property!This... View all property information
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    Location Information
    Bradenton Beach, Anna Maria Island
    5 of 5 stars Reviewed 9 June 2012
    bridgeport condo 101 was amazing!!! we had such an amazing time...and the comfort of the condo was outstanding...the service we had gotten from ISLAND PROPERTIES due to coffee...
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    $87
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    1 / 18
    4 of 5 stars (2) Very good
    Anna Maria
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Dishwasher
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
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    About this property
    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... View all property information
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    Location Information
    Anna Maria, Anna Maria Island
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    $110
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    1 / 14
    4 of 5 stars (4) Very good
    Holmes Beach
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (4) Make Enquiry
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    • Dishwasher
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • x
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    About this property
    Fountainhead Condo #5 is just a few steps from the beautiful beaches and azure blue water of the Gulf. This vacation rental is beautifully furnished and well equipped for your enjoyment. This two bedroom, two bath beach rental will sleep six with a queen size bed in one bedroom, two twin beds... View all property information
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    $1,472
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    1 / 22
    5 of 5 stars (25) Excellent
    Holmes Beach
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (25) Make Enquiry
    Amenities & Details
    • Internet Access
    • Shared Outdoor Pool...
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
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    • Wheelchair access
    • Elder access
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    About this property
    Gulfsands Condo #201, located at 4200 Gulf Drive in Holmes Beach, is a beautifully furnished two bedroom, two bath condo directly on the beach. It’s in a popular Gulf front complex with a large heated pool, elevator and undercover parking. This complex is located adjacent to the Manatee Public... View all property information
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    5 of 5 stars Reviewed 4 July 2014
    Let see where to start,this condo is very clean and well stocked with everything you can think of! Our trip here was the best we have ever had! We will be back next year! The...
    5 of 5 stars Reviewed 2 March 2013
    This is one of the best properties we stayed in. Owners/managers do a wonderful job of making sure you are in good hands. Owner called us after we arrived which was really...
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    $126
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    1 / 22
    4.5 of 5 stars (4) Very good
    Bradenton Beach
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • Dishwasher
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
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    About this property
    Welcome to the Beach House Resort, located just blocks from downtown Bradenton Beach, Florida on beautiful Anna Maria Island! This Gulf front vacation rental condo is located directly on the beach and features spectacular beach views from every unit. This unit is newly refurbished with top of... View all property information
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    Location Information
    Bradenton Beach, Anna Maria Island
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    $101
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    1 / 14
    4.5 of 5 stars (6) Very good
    Bradenton Beach
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Reviews (6) Make Enquiry
    Amenities & Details
    • Dishwasher
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
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    About this property
    The Safari Suite located at 1105 Gulf Drive South in Bradenton Beach on Anna Maria Island, FL -- The living room is decorated in a jungle motif and includes a color 46'' Sony High Definition television, VCR and DVD, sofa bed, and large walk-in closet. An eat-in kitchen has seating for 4. Brand... View all property information
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    Location Information
    Bradenton Beach, Anna Maria Island
    5 of 5 stars Reviewed 28 August 2014
    Close to beach, well equipped and quiet. Kitchen was easy to cook in and huge TV could be seen easily from living room and kitchen.
    4 of 5 stars Reviewed 24 July 2014
    My hubby and had a great week away in perfect place for two. We had everything we needed and apartment was updated and nicely appointed. It was so nice to be able just to walk...
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    $1,249
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    1 / 22
    5 of 5 stars (8) Excellent
    Holmes Beach
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (8) Make Enquiry
    Amenities & Details
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Wheelchair access
    • Elder access
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    About this property
    Anna Cabana Bungalow #4 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... View all property information
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    $183
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    1 / 18
    5 of 5 stars (25) Excellent
    Bradenton Beach
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (25) Make Enquiry
    Amenities & Details
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
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    • Wheelchair access
    • Elder access
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    About this property
    Seagrass Flats Condo #4 is an upper level, gulf side unit located at 101 25th Street North in Bradenton Beach. It is a four unit complex located near one of the widest beaches on the island and features a heated pool and barbeque area. Immediately across from the beach, you can be on the sand in... View all property information
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    Location Information
    Bradenton Beach, Anna Maria Island
    4 of 5 stars Reviewed 22 April 2015
    We actually stayed in Flat 2 but found it to be superbly located. I assume that all 4 of the units are similar in presentation -' we found Flat 2 to be very clean and comfortable...
    5 of 5 stars Reviewed 23 October 2014
    Even though the unit is across street from beach, still very close to the most beautiful sunsets which we could see from balcony. Unit very comfortably accommodated 4...
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    $153
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    1 / 25
    4.5 of 5 stars (3) Very good
    Bradenton Beach
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
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    About this property
    Enjoy a fantastic Bradenton Beach vacation in this colorful duplex filled with charming beach décor and special touches that will make your stay extra special. 'Sea Stories' features two comfortable bedrooms, one with a king-size bed, and the other with a queen. Both have flat-panel... View all property information
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    Location Information
    Bradenton Beach, Anna Maria Island
    4 of 5 stars Reviewed 9 April 2015
    We really enjoyed our stay in 1 Sea Stories. The place was clean and well stocked with appliances, towels, etc. There are beach chairs available. Check in and out was very easy...
    4 of 5 stars Reviewed 6 March 2015
    Pro: Very nice roomy vacation rental right across the street from Gulf Drive Café & Tiki Hut and beach. Con: Renting through E&V Vacations International. Went for 2 1/2 days...
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    $7,518
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    1 / 22
    4.5 of 5 stars (5) Very good
    Anna Maria
    4 Bedrooms / 4 Bathrooms / Sleeps 14
    Overview Reviews (5) Make Enquiry
    Amenities & Details
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
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    • Wheelchair access
    • Elder access
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    About this property
    The Golden Dolphin, located at 801 North Shore Drive in Anna Maria, is the ultimate in beach front luxury. This executive level gulf front home has a tropical heated pool with waterfalls, four bedrooms, a library, three and one half baths a gourmet kitchen and much more. It was custom built with... View all property information
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    Location Information
    Anna Maria, Anna Maria Island
    4 of 5 stars Reviewed 14 July 2014
    Great location, great size for multiple families. impressive kitchen and great for preparing large breakfasts/dinners; Master Suite very impressive and the showers where awesome...
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    $1,695
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    1 / 21
    4 of 5 stars (18) Very good
    Anna Maria
    2 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Reviews (18) Make Enquiry
    Amenities & Details
    • Grill
    • Internet Access
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
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    About this property
    The Anna Maria Escape located at 725 North Shore Drive in Anna Maria city is just that - a peaceful, relaxed place to get away from it all. You can stroll on the beach for miles in either direction! It’s a perfect Anna Maria Island vacation home!This spacious and charming two bedroom, two bath Gulf... View all property information
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    Location Information
    Anna Maria, Anna Maria Island
    3 of 5 stars Reviewed 25 March 2015
    We were quite pleased when we saw the exterior of the house - very attractive. When we walked in, the house was clean and presented well. There were two of us - college...
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    $200
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    1 / 22
    Anna Maria
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
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    About this property
    Welcome to the Heron located at 706 Rose unit A. This quaint 2 bedroom 1 bath duplex located on a quiet street on the north end of beautiful Anna Maria Island awaits the vacationer in you. Recently updated and all new furniture throughout will accommodate up to 4 people. There is a queen bed, 1... View all property information
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    Anna Maria, Anna Maria Island
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    $364
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    1 / 23
    5 of 5 stars (1) Excellent
    4 Bedrooms / 8 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Dishwasher
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
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    About this property
    Sitting on the Tampa Bay! Tropical flowering bushes and swaying palm trees surround this beautiful villa on the north end of Anna Maria. Sitting on Tampa Bay with panoramic views this bright and airy home is the quintessential combination of modern comfort and casual beach living. Take a chair on... View all property information
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    5 of 5 stars Reviewed 1 February 2015
    I am always a bit hesitant with rentals on line as sometimes the photos can be deceiving. This time they were completely accurate. We opened up the door and the open water...
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    $1,147
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    1 / 12
    5 of 5 stars (5) Excellent
    Bradenton Beach
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (5) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Affordable comfort and convenience for your next Florida vacation. Unit 162 at Runaway Bay Resort gives you all the amenities that you need for a wonderfully relaxing vacation on beautiful Anna Maria Island. The fully furnished 2 bedroom, 2 bath condo includes free high speed wireless internet, a... View all property information
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    Location Information
    Bradenton Beach, Anna Maria Island
    5 of 5 stars Reviewed 13 August 2011
    We had a wonderful time! This condo was exceptionally clean and had everything we could have wanted. It is a ground floor unit just a few steps from the pool, with a nice lawn and...
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    $765
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    1 / 31
    5 of 5 stars (1) Excellent
    Bradenton Beach
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dryer
    • Gym
    • Internet Access
    • Satellite TV
    • Sauna
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Runaway Bay (RAB), located on beautiful Anna Maria Island (AMI) on the Gulf coast of Florida, is an attractive condominium complex with every imaginable amenity. RAB has the Island's largest heated swimming pool, tennis courts, bocce ball, shuffleboard, and an exercise room with plenty of... View all property information
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    Location Information
    Bradenton Beach, Anna Maria Island
    5 of 5 stars Reviewed 17 June 2013
    Staying at Unit #285 at Runaway Bay was by far a much nicer choice than staying at one of the local resorts down the road where the rest of my family chose to stay. The unit was...
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    $1,140
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    1 / 19
    5 of 5 stars (1) Excellent
    Holmes Beach
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Lovely Bayside Condo recently remodeled, 2 Bedroom, 2 Bathroom, fully air conditioned, screened lanai, heated pool and covered parking. Easy access to: retail shops, grocery store and restaurants. 200 hundred yards to Free Island Trolley. Short walk to white sand beaches. Bike to nearby Robinson... View all property information
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    $166
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    1 / 10
    3.5 of 5 stars (3) Average
    Holmes Beach
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Dishwasher
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
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    About this property
    Brand New! BLUE LAGOON - Anna Maria Island's newest vacation rental villa is ready for your next vacation! Two bedroom, two bath with a huge Tropical pool and 10' waterfall right outside your back door. The pretty upgraded kitchen offer granite countertops, stainless appliances and ample... View all property information
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    $214
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    1 / 12
    5 of 5 stars (1) Excellent
    Holmes Beach
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Grill
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
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    About this property
    The 'Flip Flop' duplex is a fantastic recently remodelled duplex located one block from the white sandy beaches boasting professional landscaping, beautiful retro interiors, and its own private pool for each side of the duplex. Flop (the yellow side of the duplex) is a one bedroom, one bath duplex... View all property information
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    5 of 5 stars Reviewed 8 October 2014
    My husband and I loved Flop Cottage for many reasons. First of all, the landscaping is lush and tropical and the décor is fun and cozy - so you instantly feel like you are on...
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    $364
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    1 / 30
    4.5 of 5 stars (4) Very good
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Dishwasher
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Welcome to 717 Jacaranda just a short stroll to the sugar white sand beaches of beautiful Anna Maria Island. This tastefully updated ground level home is ideal for a family week's vacation to spending the winter here on Anna Maria Island. You will have plenty of room for the whole family with this... View all property information
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    5 of 5 stars Reviewed 30 January 2015
    This was our 2nd year staying at Au Soleil (3 weeks) and we've booked it again for next year. It's really more house than we need but is so comfortable and perfect for us. The...
    5 of 5 stars Reviewed 6 December 2014
    We have been going to Anna Maria for many years and have stayed at a number of different properties. This property was in a quiet neighborhood . We could ride our bikes without...
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    $4,587
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    1 / 13
    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Hot Tub
    • Internet Access
    • Safe
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    This a luxurious gulf front villa, ground floor, walk directly to the beach. One of 12 units, but separate villa. Master suite with king size bed. Second bedroom, 2 twin beds beautifully decorated, and den/3rd bedroom with queen sofa bed can sleep 1 or 2. Two baths, laundry room, gourmet... View all property information
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    5 of 5 stars Reviewed 6 November 2012
    This villa is beautiful and in a wonderful location on a quieter stretch of the beach. Very upscale furnishings, and perfectly outfitted. The two porches - one shady and one sunny...
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    $1,911
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    5 of 5 stars (2) Excellent
    Holmes Beach
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    traveller have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    What a great place! The first time I came to Anna Maria Island, I thought how could I get a place like this! A place where a clean shirt and flip flops are the norm. Where people say hi and the food is great and affordable. I watched my first wedding at sunset while having dinner on the beach.... View all property information
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    5 of 5 stars Reviewed 19 April 2014
    I completely agree with the previous review. We loved the view and certainly appreciated being at a walking distance to the beach and to the stores. Also the kitchen is better...
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    Holmes Beach
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
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    • Dishwasher
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    No need for shoes at this direct Gulf front condo. Out the door, down the steps, and your feet are in the sand. No streets to cross, you are on the beach! The view from your open air lanai is fantastic! You’ll love seeing dolphins swim by as you sip on your morning coffee. All day long you’ll... View all property information
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    $819
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    1 / 24
    5 of 5 stars (28) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (28) Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Limefish, from Pineapplefish is one of the most stunning beachfront holiday rentals on Anna Maria Island, with direct access to a beautiful, almost private beach. With spectacular views across the Gulf, Limefish has a wonderful and spacious decked area across the whole of the property, where you... View all property information
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    5 of 5 stars Reviewed 9 November 2014
    We were staying here with friends who were getting married on the beach. It is paradise. The villa was perfect for seven of us, though one couple had to have bunk beds, and we...
    5 of 5 stars Reviewed 7 October 2014
    Limefish has become a yearly destination tradition for my family. It is the ultimate in a beachfront location. Bike paths galore from this house, enabling touring the island...
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    $147
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    5 of 5 stars (16) Excellent
    Bradenton Beach
    1 Bedroom / 2 Bathrooms / Sleeps 4
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    You will enjoy this adorable newly renovated vacation cottage – THE LITTLE MERMAID -- on Anna Maria Island just across the street from the Gulf of Mexico and minutes from shopping and attractions on Bradenton Beach’s popular Bridge Street! Your three parking spaces are right at the front door!!... View all property information
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    Location Information
    Bradenton Beach, Anna Maria Island
    5 of 5 stars Reviewed 7 April 2015
    We enjoyed our month stay at The Little Mermaid tremendously. This little cottage is equipped with everything you need. Both the King bed and Queen sleeper sofa are very...
    5 of 5 stars Reviewed 24 October 2014
    Our experience was great from the start. Quick response from the owner Betty, follow up emails with detailed check in information. Upon arrival our first thought was that it was...
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    $121
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    5 of 5 stars (2) Excellent
    Bradenton Beach
    2 Bedrooms / 1 Bathroom / Sleeps 5
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    • Air Conditioning
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    • Safe
    • Water Views
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    • Pets allowed
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    • Suitable for children
    • x
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    About this property
    2br/1ba elevated turnkey steps from the bay, 2 blocks from the Gulf of Mexico. Fully furnished. Children's Park and kayak launch at end of street. Beach chairs, towels, grill provided. Gorgeous view of bay from front porch swing. Perfect place for relaxing family vacation. White sand beach, bay... View all property information
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    Location Information
    Bradenton Beach, Anna Maria Island
    5 of 5 stars Reviewed 12 September 2014
    This house is the perfect beach house. Located in a nice and quite neighborhood. Walking distance to the beach both sides and so close to a small park with a playground (I watched...
    5 of 5 stars Reviewed 12 August 2014
    What a wonderful place to stay! Beautiful view of the bay from my porch. Right next door there was a playground for my children to play on, after spending the day on the beach...
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    5 of 5 stars (1) Excellent
    Holmes Beach
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
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    • Suitable for children
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    About this property
    Island House 306 A 56th Street Holmes Beach , FL 34217 For true Southern Living and if only the best will do, this beautiful island vacation home has a large private pool that is electrically heated to ensure year round warm water to swim in surrounded by gardens landscaped with tropical trees... View all property information
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    Bradenton Beach
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Welcome to Hawk's Nest! Nicely updated with new designer features throughout that makes this a special spot in RunAway Bay Condo complex. This elevated 2 bedroom 2 bath condo makes you feel like you are in a luxury hotel with the beach just a short stroll away. This vacation rental condo comes with... View all property information
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    Location Information
    Bradenton Beach, Anna Maria Island
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    4 of 5 stars (1) Very good
    Holmes Beach
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Air Conditioning
    • Balcony
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    • Satellite TV
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    When you stay in this spacious two-bedroom family-friendly condo you will definitely become a beach potato! Just steps from Anna Maria Island's beautiful white sand beach in the city of Holmes Beach, with 1,349 square feet, this vacation rental provides plenty of space to relax and enjoy your time... View all property information
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    4 of 5 stars Reviewed 12 January 2015
    My husband and I traveled with our son and his fiancée. The condo is very clean, with several upgrades especially in the kitchen. Counters, appliances and provided dishes...
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    5 of 5 stars (4) Excellent
    Holmes Beach
    1 Bedroom / 2 Bathrooms / Sleeps 4
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    • Internet Access
    • Shared Outdoor Pool...
    • Waterfront
    • Water Views
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    • Pets allowed
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    • Suitable for children
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    About this property
    Seaside Beach House #103 located at 102 68th Street in Holmes Beach is a direct Gulf front complex with a heated pool at beachside. It’s one of the nicest complexes on Anna Maria Island. This 'hidden away' property is located on a quiet side street in the northern end of Holmes Beach. The beach... View all property information
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    5 of 5 stars Reviewed 26 September 2014
    Seaside Beach House on Holmes Beach, Florida is a beautifully kept unit in a 10-unit complex right on the beach. Wonderful accommodations including washer and dryer in the unit...
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    4 of 5 stars (1) Very good
    Holmes Beach
    2 Bedrooms / 1 Bathroom / Sleeps 6
    travellers have booked this property
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    • Air Conditioning
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Come relax and enjoy your beach vacation at The Cast Away! Located conveniently across from the Manatee Public Beach and the Gulf of Mexico. This two bedroom and one bath unit sleeps six with a queen size bed, two twin beds and a sofa bed. A full size kitchen and living room are included for your... View all property information
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    4 of 5 stars Reviewed 3 April 2015
    Mark was great to work with. He was very accommodating. As an extra bonus breakfast at the cafe was included which was delicious. We would stay there again.
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    5 of 5 stars (1) Excellent
    Holmes Beach
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Grill
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    • Pets allowed
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    • Suitable for children
    • x
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    About this property
    The 'Flip Flop' duplex is a fantastic recently remodeled duplex located one block from the white sandy beaches boasting professional landscaping, beautiful retro interiors, and its own private pool for each side of the duplex. Flip (the orange side of the duplex) is a one bedroom, one bath duplex... View all property information
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    5 of 5 stars Reviewed 31 May 2014
    Everyone I showed pictures of this home loved the retro look of it! The location is one block from the ocean in a very quiet neighborhood and everything you need is there. Ben...
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    1 / 27
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Gym
    • Satellite TV
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    • Pets allowed
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    • Suitable for children
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    About this property
    Come and stay at this newly renovated unit; one of two units available at this superb duplex located just 500 meter from beautiful Holmes Beach on Anna Maria Island. This spacious two bedroom two bathroom property can accommodate up to 6 persons with a queen-size bed in the master bedroom with... View all property information
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    5 of 5 stars (1) Excellent
    Bradenton Beach
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • x
    About this property
    AWESOME is the word describing this darling getaway. With tropical murals abounding and colorful furniture you will surely know THIS is a vacation! This one bedroom, one bath unit is located diredtly on the pristine Gulf of Mexico Beach. You will enjoy the sruf, miles of powder-white sandy beach,... View all property information
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    Location Information
    Bradenton Beach, Anna Maria Island
    5 of 5 stars Reviewed 30 March 2015
    We loved this space. It was just the right size for us and right on the beach. The Sandy area prior to beach area allowed us to have our dog share the beach with us. For us...
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    5 of 5 stars (8) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 7
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    • Air Conditioning
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    • Grill
    • Hot Tub
    • Internet Access
    • Private Outdoor...
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    • Pets allowed
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    • Suitable for children
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    • x
    About this property
    606 hampshire lane, holmes beach fl 34217... Exquisite home on a great extra wide canal across the street from the key royale golf club. Designer furnished with top of the line amenities. 3 king bedrooms with tvs in each, 2 bath and a bright sunroom overlooking the dock, pool and outside sitting... View all property information
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    1 / 11
    4 of 5 stars (11) Very good
    Holmes Beach
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Grill
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    • Shared Outdoor Pool...
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    • Pets allowed
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    • ?
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    About this property
    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... View all property information
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    5 of 5 stars Reviewed 9 May 2012
    After reading all of the good reviews and comments here and in the forums, we decided to contact the property management for this unit. We were pleased to receive a warm, personal...
    4 of 5 stars Reviewed 4 June 2014
    Die Unterkunft ist sicherlich ein paar Jahre alt, aber sieht neu renoviert aus. 1 Gemeinschaftspool, eigene Terrasse mit Tisch und Stühlen incl. Grill machen es einem schwer was...
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    1 / 24
    5 of 5 stars (1) Excellent
    Holmes Beach
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
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    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Elder access
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    About this property
    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... View all property information
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    Holmes Beach
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Grill
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    About this property
    Sirena del Mar is a three bedroom, two bath home located at 201 30th Street in Holmes Beach. This home has been totally renovated and features a small pool. Its two very short blocks to the wonderful, white sandy beaches.Sirena del Mar has a wonderful open design with all new kitchen cabinets and... View all property information
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    1 / 19
    4.5 of 5 stars (2) Very good
    Holmes Beach
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
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    • ?
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    About this property
    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... View all property information
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    5 of 5 stars Reviewed 12 July 2014
    A perfect place to stay. The apartment was lovely. The pool was perfect. A walk across the street to the publix supermarket and a 2 minute trip to Holmes Beach. Everything we...
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    4.5 of 5 stars (19) Very good
    Bradenton Beach
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Grill
    • Internet Access
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
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    • Elder access
    • ?
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    About this property
    The Beach House Resort #3, located at 1000 Gulf Drive in Bradenton Beach is in a gulf front complex with panoramic beach views. The white, sandy beach stretches for miles in either direction! There are numerous beach side chaise lounges to sit back and enjoy the sunsets or catch up on your reading.... View all property information
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    Location Information
    Bradenton Beach, Anna Maria Island
    4 of 5 stars Reviewed 11 October 2014
    If you want to relax, have fun and enjoy a beautiful beach right outside your screened patio, this is the place to be. The unit was very clean and well stocked. The bed was truly...
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    4.5 of 5 stars (7) Very good
    Bradenton Beach
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
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    About this property
    Spend your vacation enjoying the Island life in a quiet and well-kept family neighborhood snuggled between the Gulf of Mexico and Anna Maria Sound. Our house is less than a mile north of the Cortez bridge (SR 684) affording easy access to the mainland. Each unit has 2 bedrooms, 2 baths, A/C,... View all property information
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    Location Information
    Bradenton Beach, Anna Maria Island
    5 of 5 stars Reviewed 6 July 2014
    recently spent a relaxing time at the beach. great weather, beautiful beaches, walking distance to a variety of restaurants, enjoyed the 4th of july celebrations on the beach. a...
    5 of 5 stars Reviewed 22 June 2014
    When owner John Donato said "just a block away", he meant it! In fact one or two blocks either way got one to lovely beaches on Anna Maria Island in Florida. The rental had a...
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    4.5 of 5 stars (2) Very good
    Holmes Beach
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    travellers have booked this property
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    • Pets allowed
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    • x
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    • x
    About this property
    Spacious 3-level House with 2 large decks overlooking the beautiful Gulf of Mexico. House is fully furnished with a large flat screen TV and Bose Stereo System. Great Gulf views from living room and Master Bedroom. One Guest room also has a gulf view. Large garage is fully equipped with beach... View all property information
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    4 of 5 stars Reviewed 11 April 2015
    This house is lovely. It is well maintained and clean and has good sized rooms. The description is accurate. It is in an excellent location if you are looking for a beach week...
    5 of 5 stars Reviewed 23 January 2015
    A fantastic home, very well appointed, very clean and the perfect size for a group of 6. The location is spectacular, only steps from the beach and in the heart of Anna Maria...
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    4 of 5 stars (4) Very good
    Bradenton Beach
    4 Bedrooms / 2 Bathrooms / Sleeps 12
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    • Internet Access
    • Water Views
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    • Pets allowed
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    • Suitable for children
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    About this property
    The Dolphin Dance, located at 803 and 805 Gulf Drive South is an impressive duplex with unobstructed, panoramic views of the Gulf of Mexico. Each side has two bedrooms and one and one half baths. Each sleeps six with a queen size bed, two double beds and a sofa bed. There is a shared washer and... View all property information
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    Location Information
    Bradenton Beach, Anna Maria Island
    4 of 5 stars Reviewed 15 April 2014
    We went to Anna Maria Island for the first time with friends who had been there several times before. Our two families, both with teenage girls, each rented one side of Dolphin...
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    4.5 of 5 stars (26) Very good
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    About this property
    Honeyfish is a fabulous, single storey vacation rental from Pineapplefish. Its location, on the edge of Bimini Bay, its nautically themed complete with boating artefacts, makes Honeyfish a water lover's dream luxury home on Anna Maria Island. Honeyfish is surrounded by the water and is perfect... View all property information
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    5 of 5 stars Reviewed 2 March 2015
    We absolutely loved it here. Everything was perfect, apart from the weather! We stayed for a week and we all wished it was longer. It was our first visit to the Island and we...
    5 of 5 stars Reviewed 3 February 2015
    Honeyfish is my favourite place for a vacation. It is a spacious four bedroom house that allows all of our own space will being able to invite friends for an overnight stay...
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    5 of 5 stars (2) Excellent
    Holmes Beach
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
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    • Dryer
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    • Internet Access
    • Private Outdoor...
    • Satellite TV
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    • Pets allowed
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    • Suitable for children
    • x
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    • x
    About this property
    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... View all property information
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    5 of 5 stars (2) Excellent
    Holmes Beach
    3 Bedrooms / 7 Bathrooms / Sleeps 8
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    • Pets allowed
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    About this property
    Ultra-spacious 1520 sq ft 3 bedroom, 2.5 bath holiday condo located at 6250 Holmes Blvd in North Beach Village of Holmes Beach just 1 block from the pristine Anna Maria Island beaches. Lush landscaping gives this townhome privacy and charm. Townhouse-style layout with a 1-car garage on the ground... View all property information
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    5 of 5 stars Reviewed 9 December 2014
    We are a family of 6- grandparent ,parents and 3 children aged 8,9 and 13. When going on family holidays we normally use self catering accommodation rather than hotels and this...
    5 of 5 stars Reviewed 9 December 2014
    Our stay at Casa di Rose was just about perfect. The setup (bedrooms up, living areas down) was ideal for a night owl and an early sleeper. When our adult children and our...
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    5 of 5 stars (1) Excellent
    Holmes Beach
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Dishwasher
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    • Shared Outdoor Pool...
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    • Pets allowed
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    About this property
    Star Fish Beach 3 - Anna Maria Island's premier upscale development offers this vacation rental condo for the discriminating vacationer only. Every detail has been taken care of with our guest's relaxation in mind. A heated pool in a tropical landscape offers an oasis to relax after a long day of... View all property information
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    5 of 5 stars Reviewed 2 July 2014
    We stayed at the Starfish Beach 3 in June of 2014. This was a last minute booking (reserved a few hours before arriving) so we were very excited to get such a nice rental unit...
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    Bradenton Beach
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Balcony
    • Dishwasher
    • Grill
    • Gym
    • Internet Access
    • Private Fishing...
    • Satellite TV
    • Sauna
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Runaway Bay (RAB), located on beautiful Anna Maria Island (AMI) on the Gulf coast of Florida, is an attractive condominium complex with every imaginable amenity. RAB has the Island's largest heated swimming pool, tennis courts, bocce ball, shuffleboard, and an exercise room with plenty of... View all property information
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    Location Information
    Bradenton Beach, Anna Maria Island
    Waterfront vacation rentals on Anna Maria Island

    Whether an experienced or a first-time vacation home renter, you’ll enjoy the many choices for beachside getaways on Anna Maria Island. Luxury gulf side villas, quaint beach cottages and canal front condos offer breathing-room space and countless amenities that traditional hotel stays can’t match. Beyond the advantage of preparing some meals at home, your beach rental allows you to slide right into islander life and feel very much at home.

    “Old Florida” charm and easy island living

    Three small communities share Anna Maria Island – Bradenton Beach, Holmes Beach and Anna Maria. Each gathers along 7 miles of silky white beach overlooking the Gulf of Mexico. The island offers the village feel of Old Florida, with simple beach cottages and sandy lanes dipping under lazy Florida oaks and beachfront villas overlooking turquoise bays. There’s plenty to do on the family-friendly island, but nothing quite as important as simple relaxation. Rent a bike to roam the island or a kayak to explore the waterways. Fish, sail, comb the beaches for shells, and pack a little picnic for a sunset meal.

    One-of-a-kind dining and shopping

    Shop names reveal that island boutiques are anything but ordinary. The Painted Gate, Egret’s Landing, Paper Panache and other local establishments offer everything from resort wear to arts and crafts. The free island trolley runs North and South, as a convenient way to explore. Ginny's and Jane E's at the old IGA is a popular spot, where vintage furniture mixes with home-baked quiches and brioches in an internet café setting. One restaurant you can’t miss is Rod & Reel located at the end of a wooden pier jutting out into the bay. Kick back, fish, eat and let that tropical seascape deliver complete relaxation.

    Take a side trip south to “Shangri-la”

    Don your best resort wear and head south along Highway 789 that links Anna Maria Island to Longboat and St. Armand Keys. The gulf front drive leads you to famous St. Armand’s Circle, where elite shopping and pampered dining venues merge in an elegant European atmosphere. After a gourmet lunch, venture over to Sarasota for a visit to the cherished Ringling enclave, home to the Museum of Art and Ca d’Zan Mansion. Set in a lush 20-acre garden overlooking the water, the Venetian mansion is considered “the last of the Gilded Age mansions” built in America.

    Vacation rental homes, a superb value for families and friends

    Spacious living areas, plenty of baths and bedrooms and every imaginable amenity explain why vacation homes are today’s most popular travel choices. From the comfort of your own island getaway, you’ll enjoy every pleasure Anna Maria Island offers.