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Holiday Rentals in Anna Maria Island, FL

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    ₹ 13,981 Average
    ₹ 67,000+
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    Travellers to Anna Maria Island are booking December dates now. Secure your holiday home today, and have the perfect trip.
    1 / 20
    5 of 5 stars (5) Excellent
    Anna Maria
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    1 / 32
    5 of 5 stars (13) Excellent
    Holmes Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    1 / 33
    5 of 5 stars (10) Excellent
    Bradenton Beach
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    1 / 41
    5 of 5 stars (3) Excellent
    Anna Maria
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    It doesn't get much better than being right on the water, less than one block from the bay beach, and only 7 blocks from Pine Avenue. Sunshine Cottage couldn't be a better name, because this 3 bedroom, 2 bathroom, cottage truly lets you experience the beauty of Anna Maria Island. Enjoy dangling... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 18 February 2016
    This home is located in walking distance to restaurants and the beach with bikes available as well. It is very nicely and newly decorated. The kitchen is well stocked as well as...
    5 of 5 stars Reviewed 1 December 2015
    We enjoyed our stay at Sunshine Cottage! This home is very clean and very spacious for 6 guests. We loved the flexibility of heading to the beach or relaxing in our own...
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    1 / 24
    5 of 5 stars (1) Excellent
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    An elegant beach-house that redefines the idea of island comfort, built with love and an extreme attention to detail. Every room of the house has a unique ambiance combining color, textures and accent lighting. The outdoor area is one of the most spacious on the island with a large heated free form... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 3 April 2016
    We had a terrific stay at this delightful house. Even though we stayed during the busiest tourist week of the year, the house was the perfect oasis of calm.
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    1 / 45
    4.5 of 5 stars (15) Very good
    Anna Maria
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
    About this property
    WELCOME TO ALL DECKED OUT! Whether getting away for a family vacation, with a group of friends, for a wedding or any other occasion, our gorgeous 5 Bedroom home offers everything you could want for a relaxing holiday on Anna Maria Island.... with incredible views of the Bay! Sit by the tropical... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 14 June 2016
    We had the most amazing week on Anna Maria. The property far and away exceeded all of our expectations. Our family included 5 adults and 4 children, and we found the property to...
    5 of 5 stars Reviewed 11 May 2016
    We were so impressed with this home. We had friends and family visit, and they were very interested in future rental. With 5 bedrooms, 3 full baths, outside hose rinse off...
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    1 / 23
    5 of 5 stars (3) Excellent
    Anna Maria
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Stunning ground level 3 bedroom/2 bath home with luxury finishes at every glance. Brand new to the market and recently renovated, this home is packed with designer finishes throughout from luxury linens in all three uniquely appointed bedrooms to furnishings that make this home feel like you are... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34217
    5 of 5 stars Reviewed 3 weeks ago
    Just what our family needed for a relaxing vacation. We loved the swimming pool and that you could kayak a few hundred feet and view the manatees on the canal right from the...
    5 of 5 stars Reviewed 18 January 2016
    This canal home (just houses away from the bay) is lovely and well appointed. Our landlords, Mathias and Carren, met us at the home at check-in and showed us everything which was...
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    1 / 35
    5 of 5 stars (12) Excellent
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • Ocean Views
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    6 reasons why you will love our condos as much as we do: *VIEW! So close to the beach, with a wonderful view from the living room and master bedroom - not to mention from the roof-top terrace! *LOCATION! Close to the beach, grocery store, restaurants and everyday needs. 'We... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 28
    5 of 5 stars (9) Excellent
    Holmes Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Balcony
    • Patio
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    • Internet Access
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    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Grab your flip-flops and beach chairs! This family-friendly 3-bedroom, 2 1/2 -bath townhouse is just two quick blocks to the pristine, white sandy beaches of Anna Maria's gorgeous blue waters of the Gulf Coast. And after a relaxing day of sand and sun, come back for a refreshing dip in the heated... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 32417
    5 of 5 stars Reviewed 9 May 2016
    North Beach Village, unit 59, is a wonderful place to stay. The unit is fully equipped, and it is close to the beach. The pool is nearby, also. It was enjoyable to sit on the...
    5 of 5 stars Reviewed 22 August 2015
    We stayed on Anna Marie Island with several grandchildren. We had everything that we possibly needed for an enjoyable stay. The kids loved the feel of being in a jungle like...
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    1 / 23
    3.5 of 5 stars (3) Average
    Holmes Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • ?
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    • x
    About this property
    Situated 3 blocks from the beach and 2 blocks from the bay with a secluded yard surrounded by mangroves, this two-story pool home includes 3 bedrooms on the first floor and a regal master suite on the second floor. Comes equipped with Wifi, cable TV in all 4 bedrooms, washer/dryer, dishwasher,... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    4 of 5 stars Reviewed 12 August 2015
    The house is spacious, close to the beach, convenient to numerous stores and the main road of Anna Marie Island. The Anthony beach cottage also has plenty of parking space and is...
    5 of 5 stars Reviewed 9 February 2015
    First I want to thank the manager, April, for being helpful in arranging for my family and I to stay at this property at the last minute. She was really amazing to work with. The...
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    1 / 25
    5 of 5 stars (7) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    3 Story 'Nantucket' Style - 4 bedroom/ 3 bath villa is just a short walk to the beach! - Located at 212 85th Street, Anna Maria Island FL., the home is placed In a tropical setting, with pool great for cooling off and a large sun deck. 4 Bedrooms/3 baths, large master suite with king size bed... View all property information
    Location Information
    Anna Maria Island, Florida 34217
    5 of 5 stars Reviewed 2 September 2015
    My family and some friends rented this home for an extended weekend and it was all it was advertised to be. Comfortable, "beach" with a Cape Cod feel, located in a tropical yard...
    5 of 5 stars Reviewed 23 August 2015
    The house was perfect for my family and I. We enjoyed the beach and beautiful sunsets. The house had a pool for the kids and toys to play with. The game room was an absolute...
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    1 / 35
    3.5 of 5 stars (3) Average
    Anna Maria
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Ocean Views
    • Wi-Fi
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    A private single family residence of 4300 square feet under roof and 2800 square feet of air conditioned area. One short block to beach access to Tampa Bay. Executive Island home, located directly on beautiful and desirable Bimini Bay. Wonderful waterfront views of open water and large private... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 30 April 2016
    We had a wonderful time at this house! It met every need. It had anything you could imagine, pots, pans, dishes and seasonings of high quality. The beds were amazingly...
    5 of 5 stars Reviewed 16 March 2016
    This place felt like home from Day 1. Steve took the time for several personal messages to orient us before our stay and when we arrived we immediately fell in love with the open...
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    1 / 24
    5 of 5 stars (5) Excellent
    Holmes Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    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... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 2 June 2016
    Awesome, already booked this for next year! Easy to fond, easy to get to beach, great people to work with.
    4 of 5 stars Reviewed 19 January 2016
    We were there in January 2016 and we were very happy with the accommodations. The decor is a little dated but all the essentials were there. We enjoyed Holmes Beach and...
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    1 / 21
    5 of 5 stars (21) Excellent
    Bradenton Beach
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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
    Location Information
    Bradenton Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 2 weeks ago
    Great little cottage 50 yards from beach, Outside shower, great decor comfortable, includes all the bits needed for the beach, and the owner Betty is extremely helpful, clean tidy...
    5 of 5 stars Reviewed 26 May 2016
    Thoroughly enjoyed our stay at The Little Mermaid and AMI in general. The cottage had everything and more that we needed. Can’t think of a time where we thought of something we...
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    1 / 44
    5 of 5 stars (1) Excellent
    Bradenton Beach
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Exquisite, completely remodeled cottage located just a short walk to the beach. The cottage offers 2 bedrooms, 1 bath, top of the line amenities and tasteful decor. Kitchen has granite countertops and stainless steel appliances. This property has wireless internet, a large flat screen TV in the... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 31 May 2016
    My family of 6 with four boys ages 9-17 just returned from a week on Anna Maria Island. It was our first time in Florida and we are so glad we chose AMI! It feels as if you are...
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    1 / 23
    5 of 5 stars (1) Excellent
    Holmes Beach
    3 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    200 feet to the beach-a short one minute stroll - Gulf Views Three story with elevator, private pool and spa, gourmet kitchen with granite counter tops, double refrigerators, wine cooler, dishwasher, double oven, gas cook top, built-in microwave, disposal - all stainless steel appliances, cherry... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 13
    4.5 of 5 stars (4) Very good
    Holmes Beach
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Balcony
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    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    Location Information
    Holmes Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 19 February 2016
    beautiful apartment just a walk away from the beach! clean, well stocked, decorated in the perfect beach mode!
    5 of 5 stars Reviewed 4 July 2015
    We loved the house, very clean and tidy. The owner checked in multiple times about how things were. Loved the decor and the overall feeling of the place.
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    1 / 28
    5 of 5 stars (36) Excellent
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
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    • x
    About this property
    From the same owners of A Lime Cottage (p277325), who've been recognized as TripAdvisor "rated excellent" vacation rental, Flipkey 2012 and 2013 Top Vacation Rental, 2012 Top Rental Manager", we're delighted to now have Lemon Cottage. <BR><BR>Nestled in a quiet residential boating community across... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 26 April 2016
    Working with Chris was effortless and the best vacation rental experience. He welcomes you into his home that is stocked with any and everything you could possibly need. It has an...
    5 of 5 stars Reviewed 18 April 2016
    We have been home for a couple weeks now and really want to return! . This was our first stay on Anna Maria Island and we could not have made a better decision about where we...
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    1 / 23
    5 of 5 stars (9) Excellent
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Patio
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Overlooking the Gulf of Mexico Beach, these 1250 square feet each two bedroom beach townhouses (complex of 4 apartments) arranged on two elevated levels offer beautiful views of Anna Maria island sound. A nice yard with a access to a barbecue area and a six persons tub make our apartments an ideal... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 10 May 2016
    We stayed for 5 nights in April and were delighted with our choice. Large studio on 2 levels, spotlessly clean with great views from front and back balconies. Great location and...
    5 of 5 stars Reviewed 25 August 2015
    Great apartment with a gorgeous view of the beach! Perfect location.. walk to restaurants and bars. Very clean and equipped kitchen with everything we needed. We really enjoyed it...
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    1 / 10
    4.5 of 5 stars (7) Very good
    Bradenton Beach
    Studio, 1 Bathroom, Sleeps 5 | Quick View
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    • Balcony
    • DVD Player
    • Air Conditioning
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    • Waterfront
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Watch the sunsets over the Gulf of Mexico from your private beachfront balcony. Beautifully decorated studio apartment sleeps four adults and 1 child. King size bed and a new full size Murphy bed accommodate the adults and a fold-a-bed from the ottoman will sleep a child. The free trolley will pick... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island 34217
    4 of 5 stars Reviewed 22 December 2015
    The condo was perfect for the two of us. King size bed and the kitchen made it possible for us to not eat out for every meal. The view is spectacular and they had a nice pool. I...
    5 of 5 stars Reviewed 30 June 2015
    This vacation was absolutely perfect. The location is wonderful and my children and I had an awesome time. I did have to go buy a broom because of the sand traveling back to the...
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    1 / 36
    5 of 5 stars (1) Excellent
    Anna Maria
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Step into an ultra private, secluded, tropical paradise with a lush canal front setting in quiet cul-de-sac located on the north end of Anna Maria Island. There is a beautiful heated pool just steps outside your door. The back yard has multiple areas to relax away the day and enjoy the amazing view... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 30 September 2015
    I chose Island Oasis as it ticked every box. This is a beautiful island and the beach is very easy to access, as such I wanted a property with a pool, suitable for two couples...
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    Anna Maria
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    In a tropical setting, complete with pool and large sun deck. Just a short walk to the beach. Our visitors love biking the island and taking walking tours to the various places of interest on the island. There are four bedrooms and three baths. The master suite has a king bed and a Roman tub. The... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34217
    1 / 37
    4 of 5 stars (2) Very good
    Holmes Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    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... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    4 of 5 stars Reviewed 28 December 2015
    We've completed our trip and it was great, now we're wondering how we get our damage deposit back? Great house for our family. Nice short walk to the beach. Trolleys were very...
    4 of 5 stars Reviewed 2 October 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...
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Sauna
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Welcome to Your Anna Maria Island Paradise!! Vacation on a beautiful island that is surrounded by the warm Florida sun. This paradise getaway, known as Anna Maria Island, is seven miles of warm-white sandy beaches on the Gulf of Mexico where you can swim, walk, relax, and collect shells. This... View all property information
    Location Information
    Anna Maria Island, Florida 34217
    1 / 58
    5 of 5 stars (28) Excellent
    Bradenton Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    A unique beach cottage with a Caribbean flair and Oh sooo close to the open beach. This colorful beachy cottage features 3 bedrooms & 2 full baths with a large screened lanai overlooking a private tropical heated pool. High speed internet with domestic long distance calling is included. We provide... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 3 May 2016
    Imagine our surprise when us winter weary northerners pulled up in front of the cutest Florida bungalow we had ever seen! Three bedrooms, two full and beautifully appointed...
    5 of 5 stars Reviewed 10 July 2015
    It was everything they said and so much more.close to the beach and the bay my wife and I took a long walk every morning while waiting for the kids to get up trolly was a big help...
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    1 / 28
    5 of 5 stars (4) Excellent
    Bradenton Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Waterfront
    • DVD Player
    • Grill
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    • Satellite TV
    • Porch
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Overlook the Gulf of Mexico! Simply cross Gulf Drive South to the beach. Besides supplying all domestic necessities, we also have all the little extras: bbg grill beach chairs, towels and umbrellas, beach toys, fishing poles, a bicycle and kayaks. There are 3 apts. in this home; a 2 bedroom apt.... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 4 weeks ago
    I stayed a week at Lynn's home. We stayed in the apt on the second floor. We loved the location being within walking distance of Bridge st and being directly across the street...
    5 of 5 stars Reviewed 28 May 2016
    WELL worth every dollar plus more!!! Very impressed and well maintained! Kitchen was well stocked and everything was very clean. What's even better the beach is right across the...
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    1 / 27
    5 of 5 stars (5) Excellent
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This property is available for rentals 7 nights or more. 99 steps from the beach! Elegantly furnished two bedroom and two bath condo with brand new Tommy Bahama style furnishings. Sit by the heated pool after a stroll on the white, sandy beach of Holmes Beach just across the street! There are 18... View all property information
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    Holmes Beach, Anna Maria Island 33569
    5 of 5 stars Reviewed 22 March 2016
    The owners have provided a wonderful living space that was very clean cute and cozy. My guests were very complimentary. I can't emphasize enough the owners' responsiveness and...
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    1 / 20
    5 of 5 stars (1) Excellent
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    ANNA MARIA ISLAND #3 TOP 10 ISLAND'S IN U.S.A. Palm Isle 3203,our 2 bedroom island decorated condo is across the street from the beaches of Anna Maria Island. Steps from the heated pool and fully landscaped setting, along with all the amenities of home, your family will enjoy our beach get... View all property information
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    Holmes Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 1 December 2014
    LOVED, LOVED, LOVED this property! It's perfectly located right in the heart of Anna Marie island - easy in and out parking RIGHT in front of the villa. The villa was roomy for us...
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    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Overlooking the Gulf of Mexico Beach, on Anna Maria island 2 bedroom unit is arranged on two elevated levels for a total of 1,250 square feet. The apartment is beautifully decorated, fully furnished and has open view of the beach and is one of the Bird's Nest vacation apartments complex. The... View all property information
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    Bradenton Beach, Anna Maria Island 34217
    1 / 24
    5 of 5 stars (1) Excellent
    Holmes Beach
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    This newly remodeled Florida gem backs onto 17 acres of mangrove forest and is ideally located only 3 blocks from the beach. Reasonably priced, this quaint 3 bedroom, 1 bath cottage has a spacious backyard equipped with a pool, hammock, patio furniture, grill, brick fireplace, and picket fencing,... View all property information
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    Holmes Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 27 July 2015
    I will be going back! From reservations to communication, from check in to location and the property itself, this place is magnificent!
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    Holmes Beach
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Gulf Sound is a gulf side, ground level tri-plex located at 2814 Gulf Drive in the southern end of Holmes Beach. This five bedroom, three bath property is fully equipped with everything you need for your stay. Each unit has been updated and is comfortably furnished. It's quiet, yet close to... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 7
    5 of 5 stars (4) Excellent
    Bradenton Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Sat to Sat rentals. WE RENT SHORTER STAYS ONE WEEK BEFORE ARRIVAL DATE. Awesome tropical getaway. 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, and of course the sunsets every evening. Wifi... View all property information
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    Bradenton Beach, Anna Maria Island 34218
    5 of 5 stars Reviewed 8 September 2015
    We recently stayed here for the Labor Day holiday weekend. We have rented from Shelly before and we have always been pleased. Can't wait to go back.
    4 of 5 stars Reviewed 4 July 2015
    My small family of 4 recently rented the downstairs unit "Changes In Attitudes" from Ms. Shelley Wheeler. First off I'd like to say how incredibly helpful & understanding Shelley...
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    1 / 23
    4.5 of 5 stars (4) Very good
    Holmes Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    One bedroom one bath condo located in the courtyard. The Coconuts Beach Resort is directly on the Gulf Of Mexico Holmes Beach Anna Maria Island Florida.. 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... View all property information
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    Holmes Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 26 April 2015
    We had a wonderful few days. We were presently surprised and was upgraded to a great unit #110. We enjoyed the area very much. Looking forward to coming back next year.
    3 of 5 stars Reviewed 7 April 2015
    You are steps from a great beach, but the rental could use some updates. Mattress on one bed badly in need of replacement. A faulty air conditioner kept us awake every night.
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    5 of 5 stars (4) Excellent
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    Leave your shoes at home, step off the deck and sink your toes into the warm sand off our beach level deck. Enjoy wonderfull vistas any time of day with clear Gulf and Bay views, don't miss a minuite of our breath taking sunrise and sunsets on the roof top deck. , View all property information
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    Bradenton Beach, Anna Maria Island 34217
    1 / 21
    5 of 5 stars (6) Excellent
    Bradenton Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Anna Maria Island boasts one of the longest stretches of sugar white beaches in Florida, and clear, aqua-marine water. Enjoy the natural setting from this spectacular townhouse on Bradenton Beach. This three bedroom, two-and-a-half bath home offers direct Gulf views, a king size master suite,... View all property information
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    Bradenton Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 1 week ago
    We had a fab stay for a very relaxing week here after the madness of Disney. Everything was just perfect in the condo. The attention to detail just made it for us and all the...
    5 of 5 stars Reviewed 4 January 2016
    We traveled with our three children for what we hoped would be a completely relaxing vacation filled with sun, sand, laughter, good food and great memories. We were not...
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    1 / 31
    5 of 5 stars (1) Excellent
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    FIVE MINUTE WALK TO THE BEACH - BEACH CART PROVIDED 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,... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island 34217
    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 / 10
    5 of 5 stars (3) Excellent
    Holmes Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    510 Bayview - Private canal home 3 Bedroom / 3 Bath with private pool , maximum occupancy of 6 people. Island Elegance for the whole family!~ Come to Anna Maria Island, bring family, friends and your boat to enjoy the simple pleasures of life: sun, sand, and surf. Relax in well-appointed rooms,... View all property information
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    Holmes Beach, Anna Maria Island
    5 of 5 stars Reviewed 29 April 2016
    Had a fantastic week here nine adults and we did not bump into one another once 4double rooms and 1 twin all with their own bathrooms pool area great pity that the water display...
    5 of 5 stars Reviewed 30 December 2015
    I recently stayed at this beautiful house and it was the best decision I made for the holiday. First, the rental company was so easy to work with. There was no stress at all. Even...
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    1 / 6
    4.5 of 5 stars (2) Very good
    Bradenton Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    About this property
    Retro/surf style studio condo across from Bradenton Beach with a Gulf view that sleeps 2-4. Convenience is at your fingertips with this location. Just step out, cross Gulf Drive and you are on the beach in exactly 1 minute. A short 3 minute stroll behind the unit takes you to the bay front Public... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island 34217
    4 of 5 stars Reviewed 1 week ago
    This is basically a pleasant ground floor studio apartment with a small bathroom. Nice kitchen area (microwave and hot plate, no stove), memory foam-type king mattress, good size...
    5 of 5 stars Reviewed 8 April 2016
    What an amazing place to stay! Our family had a blast ,and would love to come back. Thank You !!!!!!
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    1 / 21
    5 of 5 stars (1) Excellent
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    Very contemporary condo (danish style), just refurnished and remodeled, and equipped with more than everything you need for a relaxing and unforgettable vacation in Paradise. The unit is inspiring and gives you a laid back feeling immediately after entering. A huge pool with lounges and sun... View all property information
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    Holmes Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 14 September 2015
    Beautiful condo with a very convenient location just a few blocks from the beach and close by shops. We stayed for more than a month and it was such a perfect getaway. Definitely...
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    1 / 21
    5 of 5 stars (2) Excellent
    Bradenton Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    Club Bamboo South is a beautiful beach front apartment resort right at the white beach of Anna Maria Island. Sarasota is only 15 minutes by car and gives access to many fantastic restaurants, cultural attractions, and ice-cream parlors. The elegant and spacious one-room studio suite features a full... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 7 March 2016
    Many Thanks, we had a great stay. The arrival was super flexible, we had no problems throughout the stay and of course the island Anna Maria is a fantastic spot for young couples...
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    1 / 25
    4.5 of 5 stars (11) Very good
    Holmes Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    If you search on Google for mahanarental it will take you directly to my website. Look for the Florida Home Tab. We installed a new heated pool and Spa in January 2016. Our island home just one block from the beach offers a one of a kind setting which gives you the pleasures of a spring-fed lake... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34218
    5 of 5 stars Reviewed 7 January 2014
    We have now stayed twice at this vacation house and loved it both times. Ken, the owner makes it so easy to book and is a real pleasure to deal with. Booking direct with the owner...
    5 of 5 stars Reviewed 23 February 2013
    Exactly as advertised. This is not someone's investment property - it is a home. It has every comfort you would need and more. Literally minutes walk from the beach, private back...
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    5 of 5 stars (1) Excellent
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    Bright and sunny condo on the second floor with view to the Palma Sola Bay and a peek-a-boo-view to the beach. Only some steps away from the white sandy beach and the turquoise water of the gulf. Ten miles of clean beaches invite you for swimming and snorkeling, walking, or only relaxing and... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 22
    5 of 5 stars (59) Excellent
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    If the dates you want are not available, please see the calendar in our other listing, the Lemon Cottage in Holmes Beach (p456143). Both homes are privately owned & managed, non-condo, residential houses in island residential neighborhoods.<BR><BR>'Old Florida charm' and 'a laid back vibe' best... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 6 days ago
    A Lime Cottage is a 5 Star Cottage. 1. Service - Chris So was outstanding. Quick to reply to email, calls or texts. Provided clear, concise communication. He made the renting...
    5 of 5 stars Reviewed 31 May 2016
    After looking for a good hotel to stay at on AMI and not finding anything that stood out I turned to a Vacation Rental. This cozy little 2 bedroom cottage popped up with 2 baths...
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    1 / 15
    4.5 of 5 stars (30) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    • x
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    • x
    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.<BR><BR>Honeyfish is surrounded by the water and is... View all property information
    Location Information
    Anna Maria Island, Florida FL 34216
    5 of 5 stars Reviewed 4 February 2016
    Anna Maria Island is a paradise away from the grind of everyday life. If you haven't been there, you must go to see and experience it for yourself! It was my family's first time...
    5 of 5 stars Reviewed 3 September 2015
    After one week at the Parks in Orlando (4 adults and 3 children aged, 9, 11 and 12), Honeyfish gave us a complete change of pace. Beautiful view and location with a pool that...
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    1 / 10
    4.5 of 5 stars (5) Very good
    Holmes Beach
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
    About this property
    517 Key Royal - Private canal home 5 Bedroom / 5 Bath with private pool, maximum occupancy of 10 people. Island Breezes and Magical Sunsets Await your arrival!~ 517 Key Royale - Beautiful View of Tampa Bay from upstairs Deck. Great house for large family - maximum 10 People, Handicap Friendly -... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
    5 of 5 stars Reviewed 27 February 2016
    This is the 1st review I've ever written! Our party of 10 absolutely loved our stay here! We loved the island and all it had to offer. This house is fantastic, so relaxing to be...
    5 of 5 stars Reviewed 4 September 2015
    Having stayed in a less than satisfactory house on the first leg of our Florida holiday, we arrived at Key Royale Drive with feelings of trepidation. OH MY!! What a fabulous...
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    1 / 17
    4.5 of 5 stars (5) Very good
    Holmes Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    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... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    4 of 5 stars Reviewed 19 August 2015
    Right on the beach! Perfect view and immediate access to the warm Gulf water. Basic accomodation, nicely done recent upgrades to unit. Mentioned to office staff under bed dust...
    4 of 5 stars Reviewed 15 August 2015
    great location , right on the beach, no need to drag beach equipment or look for toilets , Ideal for family with children, stayed in 106, access to the beach from unit, seen...
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    1 / 88
    4.5 of 5 stars (9) Very good
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    Enjoy our relaxed house with brand new heated pool and its integrated jet tubes. It is just a few steps from the beach and also to best restaurants and shops on the island. This is not a duplex, this is not a condo. This is a single family house with private garden an pool. A nice dining deck with... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    3 of 5 stars Reviewed 21 September 2015
    Having been to Anna Marie several times we decided on Turtle place and booked from the end of August until the 12th September, a total of six weeks. We enjoyed our time there but...
    5 of 5 stars Reviewed 6 October 2014
    Locally known as “The Turtle Place” its in a great location halfway up the island in a quiet residential area between Gulf Drive and Marina Drive. Very easy to find. Easy key...
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    1 / 44
    4.5 of 5 stars (6) Very good
    Bradenton Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • x
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    About this property
    Across the street from Beach! Southern exposure. Enjoy peaks gulf from top level! 4 bd 3 bath. Ample storage and ample covered parking. Enjoy the lap of luxury! Everything is like NEW. This home has had a $150K makeover with new granite counter tops. New FULL cherry wood cabinets. NEW... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 2 April 2016
    First, I must mention how kind the owner is and how easy he is to work with. It was a breath of fresh air to communicate with the owner and have him be so responsive. This...
    5 of 5 stars Reviewed 12 February 2016
    We had an amazing time on our vacation. The beach is a few steps away where we saw dolphins swimming in the ocean as the sun was setting. We spent the evenings sitting outside on...
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    1 / 20
    4 of 5 stars (1) Very good
    Holmes Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • ?
    About this property
    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 queen... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    4 of 5 stars Reviewed 4 March 2016
    The reservation, payment was easy and when we arrived things were ready for us. Staff was friendly and answered all questions, we had no problems. Property was nicely landscaped...
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    1 / 45
    3 of 5 stars (1) Average
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Adriel's Place in Anna Maria...located in upscale private golf club neighborhood, a stone throw from pristine beaches, restaurants and island entertainment ( less than 1 mile ). An expansive backyard dotted with majestic palms, papered terrace and pool overlooking sailboat water. Fishing and... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    3 of 5 stars Reviewed 8 October 2015
    The island is a wonderful place. The beaches are beautiful, plenty of things to do with your family: walking, biking, boating, and just enjoying the weather. I will now list the...
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    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.