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Holiday Rentals in Anna Maria Island, FL

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    ₹ 13,991 Average
    ₹ 67,000+
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    Travellers to Anna Maria Island are booking August 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 / 24
    5 of 5 stars (1) Excellent
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | 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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    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Satellite TV
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
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    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
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    Anna Maria Island, Florida 34217
    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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    • x
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    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 / 33
    5 of 5 stars (10) Excellent
    Bradenton Beach
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Patio
    • DVD Player
    • Porch
    • Air Conditioning
    • Outdoor Dining Area
    • Secure Parking
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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
    Location Information
    Bradenton Beach, Anna Maria Island 34217
    4 of 5 stars Reviewed 2 May 2016
    Anna Maria Island is fantastic. Our place, Beach House, was a short two blocks from a great beach with hardly no other people on the beach. The rental was not fancy but clean and...
    5 of 5 stars Reviewed 23 September 2015
    The house was very well equipped and nicely decorated. Everything was provided for us including bath & beach towels. There were even extra throw blankets for sitting and watching...
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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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    • 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 4 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 / 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
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    • 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 3 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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    Anna Maria
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
    • DVD Player
    • Satellite TV
    • Grill
    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Sea Waves cottage is located at north end of anna maria island. Brand new renovation, 3 bedroom with 2 bath room, with private dock, sailboat direct to bimini bay, unobstructed , natural view of bimini bay. Less than three minute walk to beach, walking distance to pine ave and the city pier and... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Anna Maria
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Beautiful, recently renovated 1700 sf home that accommodates up to 8 people. Only a few steps to amazing sandy gulf beach. Enjoy all the amenities of a single level well appointed home with no stairs where you can step out to the beautifully landscaped pool area from your master bedroom or open... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34217
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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
    • Grill
    • Parking
    • Patio
    Suitability
    • 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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    Anna Maria
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Porch
    • Washer
    • Air Conditioning
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    • Private Outdoor...
    • Balcony
    • DVD Player
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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 / 45
    4.5 of 5 stars (15) Very good
    Anna Maria
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
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    • Satellite TV
    • Balcony
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    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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 / 20
    4 of 5 stars (1) Very good
    Holmes Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
    • Waterfront
    • Air Conditioning
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    • Grill
    • DVD Player
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    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 / 27
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Satellite TV
    • Grill
    • Washer
    • Wi-Fi
    • Balcony
    • Air Conditioning
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Located in the heart of Anna Maria Island in the sun-drenched community of Holmes Beach is 'Seacrest' where you can enjoy island living at its best in this stunning destination.Our light & roomy 2 bedroom condo (one of only four in a quiet location being in a little cul-de-sac) is recently updated,... View all property information
    Location Information
    Anna Maria Island, Florida FL 34217
    5 of 5 stars Reviewed 8 October 2015
    We have visited Seacrest 2 condo 1 several times previously and it was even better than we remembered. It was spotless and beautifully decorated. All of the rooms are spacious and...
    5 of 5 stars Reviewed 22 September 2015
    when I say Home from home that's not strictly true as I do not have the fabulous views over Palm Trees and I can't hear the beautiful sound of the ocean from my home in the UK...
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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
    • Parking
    • Air Conditioning
    • Grill
    • Washer
    • Patio
    • Internet Access
    Suitability
    • 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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    Holmes Beach
    1 Bedroom, 1 Bathroom, Sleeps 8 | Quick View
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    • Terrace
    • Air Conditioning
    • Internet Access
    • Grill
    • Balcony
    • DVD Player
    • Washer
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    Two bedroom two bath condo located upstairs 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 6 to... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 21
    5 of 5 stars (2) Excellent
    Bradenton Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Terrace
    • Balcony
    • Parking
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    • Satellite TV
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    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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 / 21
    5 of 5 stars (6) Excellent
    Bradenton Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Air Conditioning
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    • Hot Tub
    • Wi-Fi
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    Location Information
    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 / 35
    5 of 5 stars (12) Excellent
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Washer
    • Ocean Views
    • Balcony
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    Suitability
    • 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
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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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    • DVD Player
    • Satellite TV
    • Waterfront
    • Air Conditioning
    • Internet Access
    • Washer
    • Patio
    • Sauna
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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 / 27
    5 of 5 stars (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Ocean Views
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Are you two families vacationing together or maybe grandparents that are traveling with children and grand children? Rent our two units that are located right beside each other, giving you a total of 4 br, 4 ba and 2662 sqft. You'll have the best combination of closeness and privacy! They are... View all property information
    Location Information
    Anna Maria Island, Florida 34217
    5 of 5 stars Reviewed 3 weeks ago
    My "significant" birthday involved me and my closest girlfriends truly unwinding from our very busy lives. The place is extremely clean and well appointed. We prefer to prepare...
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    1 / 20
    5 of 5 stars (1) Excellent
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Enjoy paradise in this 2 bedroom, 2 bath suite. Newly renovated with all the amenities. The master suite features a king size bed with new dresser and night stands. The second bedroom has a queen bed with new dresser and night stands with large double closet. Each bathroom is full with either walk... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 1 week ago
    Shared the condo with my wife, son, his wife and my beautiful grand daughter (16 months old) who we don't see often enough. Very comfortable accommodations. Nicely equipped...
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    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    Two bedroom two bath condo located upstairs 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 6 to... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 23
    5 of 5 stars (1) Excellent
    Holmes Beach
    3 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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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 / 10
    4 of 5 stars (8) Very good
    Bradenton Beach
    Studio, 1 Bathroom, Sleeps 5 | Quick View
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    • Balcony
    • DVD Player
    • Air Conditioning
    • Patio
    • Satellite TV
    • Waterfront
    • Grill
    • Internet Access
    Suitability
    • 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 / 29
    5 of 5 stars (18) Excellent
    Holmes Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Patio
    • Internet Access
    • Grill
    • DVD Player
    • Air Conditioning
    • Private Outdoor...
    • Satellite TV
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    http://www.villachezshell.com Villa Chez Shell is a newly renovated Mediterranean beach home that offers a luxurious getaway. The highlight of this newly renovated 3 bedroom and 3 bathroom property is its tropical private backyard complete with a lagoon shaped pool and a soothing stone waterfall.... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 3 days ago
    This was our second stay in this home and we have already booked for next year. The house is wonderful, the owners don't miss any detail to make this home a perfect find.
    5 of 5 stars Reviewed 6 days ago
    The property is well kept and clean the owners have thought of everything you can imagine ! We had all necessity's for the beach and information at our finger tips about the...
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    Holmes Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
    • Grill
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    • DVD Player
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    • Washer
    • Waterfront
    • Balcony
    Suitability
    • 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
    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 / 52
    5 of 5 stars (19) Excellent
    Holmes Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    A brand NEW 2300 sq/ft, 3 bedroom modern beach house with heated and very private pool. A perfect location just steps from the beach, marina and the main plaza with great shops, a grocery store and restaurants. No need to drive anywhere. Located in a quiet neighborhood with tropical greenery, large... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 4 weeks ago
    We stayed at the Happy Island Cottage for 5 nights. The location of the home is wonderful, very short distance to everything on the island. A few of our favorite things about the...
    5 of 5 stars Reviewed 4 June 2016
    Just had a lovely stay at Happy Island cottage. Everything was as described and we couldn't have been more comfortable. The attention to detail was superb with everything we...
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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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    1 / 11
    3 of 5 stars (1) Average
    Holmes Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    This lovely property features a tropical setting surrounding a heated swimming pool. The six unit complex is located one block from the beach. Great for family reunions or wedding parties. This unit is a one bedroom one bath full size apartment. King bed in bedroom and a sofa sleeper in the living... View all property information
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    Holmes Beach, Anna Maria Island 34217
    3 of 5 stars Reviewed 3 weeks ago
    Location is wonderful, villa is clean and nice pool. A little outdated, but had necessities. We have 2 adults and two teens. Would be much better suited for just two adults, as...
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    1 / 6
    4.5 of 5 stars (3) Very good
    Bradenton Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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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
    5 of 5 stars Reviewed 5 days ago
    Great little vacation spot. Located in a small shopping plaza however overall great place. Beach access across the street. Studio was very clean and perfect size for a couple...
    4 of 5 stars Reviewed 2 weeks 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...
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    1 / 19
    5 of 5 stars (1) Excellent
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    300 FEET TO THE BEACH 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... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 24 May 2016
    We have rented before in Bradenton Beach. This is our first time staying at Runaway Bay. We found everyone to be very helpful and friendly. Our unit was stocked with everything...
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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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    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 / 32
    4.5 of 5 stars (22) Very good
    Holmes Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Fantastic 2 bedroom / 1.5 bath townhome just 200 steps to the beach. Relax in Paradise at #116 52nd Street in Holmes Beach on Anna Maria Island and enjoy all the comforts that this beautifully furnished townhome has to offer. Newly decorated with granite countertops, stainless steel appliances,... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    4 of 5 stars Reviewed 30 August 2015
    Quite simply - we will be back! Having never been to AMI it was a lottery choosing where to stay. We won! Brilliant location. Shops and restaurants literally around the...
    4 of 5 stars Reviewed 21 August 2015
    Our week in Holmes Beach was amazing. The townhouse was exactly as advertised and photographed. We were delighted to find everything as clean and comfortable as hoped. Our family...
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    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
    Location Information
    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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    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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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 / 33
    5 of 5 stars (1) Excellent
    Bradenton Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Location, location, location. The 3 most important things to consider in a vacation rental. Tucked back on a VERY peaceful setting. Brick patio courtyard and PRIVATE outdoor covered patio set with umbrella. This is a desired ground level end unit in a Key West styled 4 plex. Nestled under several... View all property information
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    Bradenton Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 2 June 2016
    Myself, my husband and my 83 year old mother stayed in unit #4 (2 bedroom, 1 bath). It was a ground floor unit and was very clean and cozy. You don't generally meet the owners of...
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    1 / 13
    4.5 of 5 stars (5) Very good
    Holmes Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Apartment 8 is located on the upper level. It has one bedroom with a queen size bed and there is a pull-out sofa in the living room. The apartment has its own private balcony with stunning beach and sunset views. There is also a large shared deck with tables and chairs which overlooks the pool.... View all property information
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    Holmes Beach, Anna Maria Island 34217
    4 of 5 stars Reviewed 27 April 2016
    Very nice rental that allowed a 1 night stay for house hunting on Anna Maria Island.The owner was delightful and very accomodating!
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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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    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 / 11
    3.5 of 5 stars (2) Average
    Holmes Beach
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    About this property
    Located in Holmes Beach, on Anna Maria island. This one bedroom two bath unit is a full size apartment with full size kitchen all appliances dishwasher, stove full size refrigerator, living area, dinning area and a separate bedroom has a king size bed. Its just steps to the beach. Covered... View all property information
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    Holmes Beach, Anna Maria Island 34217
    3 of 5 stars Reviewed 8 September 2015
    It is very close to the beach. You don't have to cross a street when walking to the beach, which is a plus. The unit could benefit from some TLC. The furniture are dated. The...
    4 of 5 stars Reviewed 19 May 2015
    The location and price is what makes this place so great. It outdated, not the cleanest, and not the most comfortable BUT it's in a perfect location with all the necessities (cold...
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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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    • x
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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.<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 / 12
    5 of 5 stars (3) Excellent
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Welcome to paradise on Anna Maria Island! This 2 bedroom bayfront vacation condo has spectacular views stretching south from the Sarasota skyline all the way north to the Sunshine Skyway. Relax on the patio of this Bradenton Beach condominium rental, or in the pool and watch the dolphins play and... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 5 January 2016
    Wow! We rented unit 506 for the week of 26 Dec - 02 Janaury 2016. Bottom-Line, the unit was amazing! The heated pool, the sunrise from the balcony overlooking the bay, the...
    5 of 5 stars Reviewed 5 July 2013
    Typically speaking, we rely on reviews on TripAdvisor to decide where to stay. We took a chance on this one because there weren't any reviews, yet. Wow - are we thrilled we did...
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    1 / 25
    5 of 5 stars (14) Excellent
    Bradenton Beach
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • x
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    About this property
    Newly decorated 10/15/13. New AC unit 08/10/2014. Nice two bedroom, one bath Condo across the street from the Gulf of Mexico Beach. Very well furnished w/stainless steel appliances. Also WIFI for your enjoyment, cable T.V , bluetooth stereo and free US long distance. Condo has a queen bed in the... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 16 October 2015
    Location was perfect. Cross the street to a gorgeous, spotless, coral sand beach. Free trolley runs the length of the island and the stops are less than a block from the condo...
    4 of 5 stars Reviewed 30 September 2015
    The condo is very nicely decorated with a beach theme. Larry was very pleasant to work with. The beach is literally just across the street.
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    Holmes Beach
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    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
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    Holmes Beach, Anna Maria Island 34217
    1 / 12
    4.5 of 5 stars (5) Very good
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    Beachy and bright condo on the second floor of a small 2-story-building (20 units in total), overlooking the mangroves with view to the Palma Sola Bay. Only some steps away from the ocean and the wonderful wide and powder sanded beaches. The condo is recently refurnished; masterbedroom with a... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    4 of 5 stars Reviewed 5 August 2013
    We stayed for 4 nights at the appartment and enjoyed all our time there. The appartment is well situated on easy access routes, across the way from the Publix and a brisk walk...
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    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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    1 / 28
    5 of 5 stars (9) Excellent
    Holmes Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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 / 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
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    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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    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.