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Beach Rentals in Anna Maria Island, FL

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    Travellers to Anna Maria Island are booking March dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 43
    5 of 5 stars (10) Excellent
    Anna Maria
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    1 / 21
    5 of 5 stars (19) Excellent
    Bradenton Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 26
    5 of 5 stars (11) Excellent
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Holmes Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Ocean Views
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    About this property
    This Gulf Front is an elevated property with great gulf views. . We rent Saturday to Saturday until one week before arrival dates. If available at that time, we can rent less than the 7 days.Caribbean Casual is decorated with Tropical paintings and murals, to complete the ambiance of your... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 10
    4.5 of 5 stars (4) Very good
    Holmes Beach
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    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 - 5/5 Home on Canal w/Fenced Pool, no Cage, Pool Heat Optional @ $25 per Day Additional amenities include:... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
    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...
    5 of 5 stars Reviewed 26 July 2014
    We had an absolutely fabulous holiday at this property. Absolutely couldn't fault it. The house was perfect - very well fitted out with absolutely every you could need. The two...
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    1 / 23
    5 of 5 stars (2) Excellent
    Anna Maria
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
    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...
    5 of 5 stars Reviewed 25 August 2015
    These house is confortable,clean, cozy!! Confortable rooms!.You can see the fresh water from the window ! Walk 10 steps to a nice private deck, with beautiful birds, manatees...
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    1 / 10
    5 of 5 stars (2) Excellent
    Holmes Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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, dine alfresco, cruise from your private dock to the bay and private pool, or you simply cover yourself... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
    5 of 5 stars Reviewed 29 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...
    5 of 5 stars Reviewed 21 May 2015
    This house at 510 Bayview was phenominal!! We couldn't have picked a more perfect house for our vacation. It has everything...A beautifully landscaped inground swimming pool, 40...
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    1 / 23
    5 of 5 stars (8) Excellent
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Patio
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    • Satellite TV
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    • Balcony
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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 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...
    5 of 5 stars Reviewed 17 June 2015
    We had a great week in this lovely rental,the house was well equipped , very clean and ideally situated.The owners were very friendly and provided everything we needed.It was...
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    1 / 12
    4.5 of 5 stars (3) Very good
    Holmes Beach
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Balcony
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    • Pet-friendly
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    About this property
    Come relax and enjoy your beach vacation at The Cast Away! Located conveniently across from the Manatee Public Beach and the Gulf of Mexico. This two bedroom and one bath unit sleeps six with a queen size bed, two twin beds and a sofa bed. A full size kitchen and living room are included for your... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    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.
    4 of 5 stars Reviewed 11 May 2015
    Villa clean and very comfortable any queries were answered and delt with quickly. Downside was next busy road.
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    Bradenton Beach
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • DVD Player
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    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
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    1 / 41
    5 of 5 stars (2) 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, ½ 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 your feet off... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    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...
    5 of 5 stars Reviewed 4 November 2015
    This charming cottage was perfect for a relaxing getaway. The house is well kept, cute and fully met our needs. We took full advantage of the pool each day. I like that the owners...
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    1 / 20
    4.5 of 5 stars (3) Very good
    Holmes Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
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    • Pet-friendly
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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
    Location Information
    Holmes Beach, Anna Maria Island 34217
    4 of 5 stars Reviewed 3 weeks ago
    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...
    5 of 5 stars Reviewed 31 December 2015
    Perfect for a couple, off the main drag and steps to beach. Heated pool and a bench to watch the wonderful sunsets. Will come back to this place. Very affordable with all...
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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
    • Patio
    • Satellite TV
    • Waterfront
    • Grill
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    • Pet-friendly
    • Wheelchair access
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    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 29 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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    Anna Maria
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Balcony
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    About this property
    This gorgeous three story home in the city of Anna Maria, is an easy walk from Pine Avenue and the City Pier, with direct water views, front and rear, from all living spaces. With 5 bedrooms, 5 baths,4 balconies,3 living areas, an elevator, and a heated salt water pool, you have everything you... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 23
    4.5 of 5 stars (4) Very good
    Holmes Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
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    • Pet-friendly
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    • x
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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
    Location Information
    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 6 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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    1 / 28
    5 of 5 stars (8) Excellent
    Holmes Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Satellite TV
    • Internet Access
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    • Pet-friendly
    • Wheelchair access
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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 21 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...
    5 of 5 stars Reviewed 11 August 2015
    This condo was very comfortable, clean, beautifully decorated and fully furnished with all the comforts of home. The kitchen had everything we needed and more! We enjoyed eating...
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    1 / 32
    5 of 5 stars (13) Excellent
    Holmes Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    **DISCOUNTS FOR RENTALS OF 28 NIGHTS OR MORE ANY TIME OF YEAR** *****PLEASE ASK US ABOUT SPECIAL PRICING FOR YOUR STAY***** LARGE HEATED FREE-FORM, LUXURY POOL AND SPA WITH SPACIOUS PAVED SURROUND - ADDED AUGUST 2014 TOGETHER WITH TROPICAL LANDSCAPING, AUTOMATED GARDEN LIGHTING AND LARGE GROUND... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 21 December 2015
    Every since we booked this vacation rental we knew it would be great because of the interaction with the owners. They were on top of everything and went out of their to help us...
    5 of 5 stars Reviewed 15 October 2015
    My husband, parents and two boys decided to vacation in Florida this summer. We have always vacationed at hotels or all inclusive resorts. For this vacation we wanted to find a...
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    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
    1 / 33
    5 of 5 stars (9) Excellent
    Bradenton Beach
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Patio
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    About this property
    2br/1ba elevated turnkey steps from the bay, 2 blocks from the Gulf of Mexico. Fully furnished. Children's Park and kayak launch at end of street. Beach chairs, towels, grill provided. Gorgeous view of bay from front porch swing. Perfect place for relaxing family vacation. White sand beach, bay... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 22 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...
    5 of 5 stars Reviewed 21 September 2015
    My wife, 3-year-old daughter, and I thoroughly enjoyed our stay at this location. It is within a 5 minute walk to the beach and is a great location to easily access the...
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    On the Gulf of Mexico.. steps from the Beach. On Beautiful Historic Anna Maria Island, One BR.w/ sleep couch sleeps 4.on 2nd floor overlooking pool & garden Fullly equipped Kitchen, with Microwave . 2 TV's, wi-fi, cable New furnishings. Pool & Hot Tub, Washer & Dryer on site. Restaurants... View all property information
    Location Information
    Anna Maria Island, Florida 34217
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    1 / 33
    5 of 5 stars (8) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • x
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    About this property
    606 hampshire lane, holmes beach fl 34217... Exquisite home on a great extra wide canal across the street from the key royale golf club. Designer furnished with top of the line amenities. 3 king bedrooms with tvs in each, 2 bath and a bright sunroom overlooking the dock, pool and outside sitting... View all property information
    Location Information
    Anna Maria Island, Florida 34217
    5 of 5 stars Reviewed 14 March 2014
    As others have stated, the pictures do not do this home justice! The common space is allocated in such a way that there are four different conversational areas and an office...
    5 of 5 stars Reviewed 12 December 2013
    From the time you step into this spectacular home and thru the expanse of glass view the lagoon like location you will feel the special ambiance of Gail's Sanctuary. From the most...
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    1 / 21
    5 of 5 stars (5) 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
    Location Information
    Bradenton Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 3 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...
    5 of 5 stars Reviewed 31 May 2015
    We spent two weeks in this gourgeous place with our 3-year old and my parents in law. We all had a great time, the house was perfect and we really enjoyed the stay, all of us!
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    1 / 27
    5 of 5 stars (4) Excellent
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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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
    Location Information
    Holmes Beach, Anna Maria Island 33569
    5 of 5 stars Reviewed 29 May 2013
    We had such a relaxing time during our stay. The condo is very clean and comfy with lots of little touches to make your stay even better. Its cozy enough for a couple but also has...
    5 of 5 stars Reviewed 15 May 2013
    The accommodations were great! This unit is very accessible to the beach; it is right across the street and it was easy to walk to with my wife and 15 month old child. The unit is...
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    Anna Maria
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    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
    Bradenton Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Satellite TV
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    • Waterfront
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    • Pet-friendly
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    About this property
    Living on the beach is great !!!!! This lovely beach front 1 BR/1BA Condo is located at 1000 Gulf Dr., Bradenton Beach Fl. 1 flight of stairs from the beach with spectacular direct views of the Gulf of Mexico and Bay. Unit comes Turnkey Furnished with top of the line furnishings including a Queen... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island 34217
    1 / 46
    4.5 of 5 stars (9) Very good
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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 20 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 / 20
    5 of 5 stars (1) Excellent
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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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    1 / 7
    5 of 5 stars (4) Excellent
    Bradenton Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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 3 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 / 41
    4.5 of 5 stars (15) Very good
    Bradenton Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Delightful getaway located on Bradenton Beach on Anna Maria Island. This ground floor condo with beautiful views is directly across the street from the white powder sand beach. Slow down and experience the charm of 'Old Florida'. Enjoy beautiful sunsets. Walk to nearby unique shops and restaurants,... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 17 December 2015
    Very convenient to beach, restaurants, & shops. It has a nicely furnished kitchen, lots of beach accessories and we will likely return again.
    4 of 5 stars Reviewed 9 March 2015
    As beautiful as pictures presented. Very clean with adequate supplies furnished. A beautiful view of ocean across road from us....wonderful beautiful beach just a short walk...
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    1 / 15
    4 of 5 stars (1) Very good
    Bradenton Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Relax in the casual comfort of an island paradise, and have a true Old Florida experience on Anna Maria Island, where riding bikes is the preferred way to travel and indulging in the simple pleasures of life - sun, beach, scuba dive, Snorkel and relaxation are the favorite past times. Enjoy and... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island 34217
    4 of 5 stars Reviewed 9 March 2015
    We enjoyed our holiday on AMI. Our condo was very comfortable, clean and complete. We toured the island by bicycle and car. The beach is just across the street
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    1 / 19
    5 of 5 stars (1) Excellent
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Lovely Bayside Condo recently remodeled, 2 Bedroom, 2 Bathroom, fully air conditioned, screened lanai, heated pool and covered parking. Easy access to: retail shops, grocery store and restaurants. 200 hundred yards to Free Island Trolley. Five minute walk to white sand beaches. Bike to nearby... View all property information
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    Holmes Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 12 March 2014
    The moment we arrived, exhausted after many delays and problems, the Thomas' home became our home. The condo is well appointed, with comfortable beds, a wonderful kitchen and a...
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    Holmes Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    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
    Bradenton Beach
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Thank you for considering my home which has been recently updated to provide the warmth and feel of a true beach cottage. Wooden ceiling planks have been added along with pine beach chic cabinets and decor. I put many hours into the design of the home to provide a feeling of tropical relaxation.... View all property information
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    Bradenton Beach, Anna Maria Island 34217
    1 / 22
    5 of 5 stars (19) Excellent
    Anna Maria
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    4 Bedroom 5 bath luxury beach front house sleeping 8 with heated pool separate spa numerous decks and stunning beach views from every room. We are located on the desirable family friendly island of Anna Maria. The house is direct beach front on the quiet upmarket north end of the island. Recently... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 28 October 2015
    We couldn't have been happier with our vacation to AMI. Nigel and Maggie's home was perfect for our family! The home was pristine and stocked with anything we would need during...
    5 of 5 stars Reviewed 30 September 2015
    My family and I have enjoyed many high-end beach rental homes over the last 10 years and this home in Anna Maria is exceptional! A couple highlights that cause this property to...
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    1 / 9
    5 of 5 stars (1) Excellent
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Our Holmes Beach duplex, 2 bedroom and 2 bath home is just a short walk, (500 feet), from the beach. We are west of Gulf Drive and north of the Holmes Beach public beach. The downstairs living area has a full kitchen with appliances, spacious dining and living area and a full bath. Upstairs are... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 31 December 2015
    This was the most amazing place to stay. From the condo to the location and lets not forget to mention Fran and Bob who by the way was absolutely wonderful. Bob and Fran made us...
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    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    5 minutes walk to the beach! Totally renovated, furnished 2 bedroom / 2 full bath townhouse. Tile floors, new kitchen & breakfast bar area, granite countertops and stainless steel appliances. Ground floor has additional kitchenette, full bathroom, large living room area. 2nd floor - two large... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    Anna Maria
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Cute and Cozy Cottage just 200 steps to Beach. Walk to Shops, Free Trolley, Resturants, Pier, Museum and more. This apt is attached to another unit that shares the pool. Rent it for the whole family. All the comforts of home. Just bring you towel and suit. Beautiful Beach and Wildlife.... View all property information
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    Anna Maria, Anna Maria Island 34216
    1 / 27
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 / 13
    5 of 5 stars (1) Excellent
    Holmes Beach
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    Charming cottage-style duplex 2 blocks from beach with sugary sand and safe swimming in the beautiful Gulf of Mexico. Walk to restaurants, shops, library, laundry, & more. Clean & well appointed with tasteful modest furnishings provide a comfortable relaxing & quiet home away from home, or base... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 13 August 2015
    My girlfriend and I had a great experience the Dolphin Duplex. We were in town for a big family reunion and had a lot to coordinate. The owner of Dolphin Duplex was...
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    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Pristine Waters Await your Arrival!~ Gulf Watch Condo---2 bedroom, 2 bath condo in 32 unit complex with heated pool. Gulf to Bay setting. washer/dryer in unit. About 1200 square ft. Convenient walk to restaurants and shops. Covered parking. Week minimum. Additional amenities include: #of units... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island
    1 / 13
    4.5 of 5 stars (3) Very good
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Peaceful Easy Island Living!~ Two bedrooms with en suite full baths this 2nd floor sun filled end unit condo is in the quiet Gulf Watch 32 unit complex with heated pool and sun deck. Open floor plan with large great room. Has full kitchen, dishwasher and in unit washer/dryer. Cable TV, 42' HD... View all property information
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    Bradenton Beach, Anna Maria Island
    5 of 5 stars Reviewed 4 July 2015
    104 Gulf Watch was exactly what we were looking for. Location was superb. Close to restaurants, stores and most important right across from the beautiful gulf water. Unit was...
    4 of 5 stars Reviewed 16 March 2012
    We two retired couples had a great time staying on Anna Maria Island again for 2 wks. The condo was very nice and the owner very nice to work with. The pics as shown were just as...
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    Holmes Beach
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    This two bedroom, two-bath condo has been tastefully renovated and refurbished. The kitchen has new appliances and granite countertops. All the new furnishings make this a very comfortable home away from home. It has a private screened balcony off the living room and bedroom that overlooks the... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    Anna Maria
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Enjoy an old fashioned Florida beach vacation at this wonderful cottage just 4 houses from the beach! One Florida family has spent over four decades building happy summer memories right in this spot, and they invite you to create some of your own treasured moments on your next visit to Anna Maria.... View all property information
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    Anna Maria, Anna Maria Island 34216
    1 / 8
    5 of 5 stars (6) Excellent
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    This well-furnished two bedroom condo is next to a quiet nature preserve and has a fine view of the bay separating Anna Maria Island from Florida's mainland as well as the Sandy Pointe heated swimming pool. The beach is just 2 blocks away with its bright white sand and aquamarine waters. For... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 10 April 2015
    We loved our condo. It had plenty of room for our family which included 2 teens. The trolley stop a short walk a away and easy walk to the beach. Our condo was fabulous. Well...
    4 of 5 stars Reviewed 22 January 2011
    A very well appointed apartment in a great location that had everything you would wish for to enhance your vacation experience. A real home from home that is clean, well...
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    Holmes Beach
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    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
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    This gorgeouse condo, has balcony view of the beach. From the roof balcony you can see miles of beach and beautiful gulf waters. This spacious condo, has two nice size bedrooms, with two balconies, fully equiped kitchen, flat screen tv, really nice sofa that makes into sleeper. The complex has... View all property information
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    Holmes Beach, Anna Maria Island 34217
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Fantastic location at Runaway Bay on gorgeous Anna Maria Island. The resort has wonderful amenities including large heated pool, exercise room, tennis and bocce court, fishing pier and private access to the beach. This 2 bedroom 2 bath condo is quiet with a pretty lagoon view and has free wifi and... View all property information
    Location Information
    Anna Maria Island, Florida 34217
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    WELCOME TO YOUR ANNA MARIA ISLAND PARADISE! Vacation on a tranquil island embraced by the warm Florida sun. This quaint paradise getaway, known as Anna Maria Island, is complete with the 'Old Florida Style' charm. Seven miles of warm-white sandy beaches on the Gulf of Mexico to swim, walk, relax,... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Anna Maria
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    This unit is a Wonderful Beach Vacation Spot ! It is fully furnished, with 2 TV's, Wi-Fi, Cable , pool, hot tub, Patio with 2 grills, directly on the BEACH - with fabulous Gulf of Mexico blue water. There is a 5 Star Zagat rated resturant on the property. There is twice weekly maid service and... View all property information
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    Anna Maria, Anna Maria Island 34228
    1 / 24
    5 of 5 stars (4) Excellent
    Bradenton Beach
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    Located in a quiet neighborhood in a narrow part of Anna Maria Island. Being just 60 steps away from a wide and never crowded beach makes it easy to take numerous beach trips throughout the day. The free island trolley is close-by when you want to explore the island and don't feel like driving. An... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 3 weeks ago
    Alex is da man and so is his house. His website, Flip Key, is true and the pictures, etc. are exactly how things are. Alex is a gentleman. Loves his house and wants you to be...
    5 of 5 stars Reviewed 18 August 2015
    The house was great. It was very clean and had plenty of room for everyone that was with us. Alex was wonderful! He had great suggestions about places to eat and what to do 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.