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Pet Friendly Holiday Rentals in Anna Maria Island

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    Travellers to Anna Maria Island are booking December dates now. Secure your holiday home today, and have the perfect trip.
    226 Matching Rentals in Anna Maria IslandView all 1,277 rentals
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    Gorgeous views,spectacular home!1 / 46
    (34)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    250 Feet from the Beach1 / 25
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Cast Villa 11 / 31
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Ocean Views
    • DVD Player
    • Central Heating
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Anna Maria Island is still old Florida, I am on a half acre of very Tropical Palms and landscaping. Located in the heart of the Island. Directly accross from the Famous Manatee County Public Beach. Reasturants, Free trolley all right there. Also grocery, pharmacy, shopping within walking distance....
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Casa Playa West  is a Luxury 4 bedroom home with a pool and elevator!1 / 37
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Ocean Views
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home provides you with your own private pool. It has virtually EVERYTHING you need for a perfect Island vacation. This home has a private pool and is less than a block to the beach and 1 block to Sarasota Bay for fishing. Walk to Sarasote Bay and watch the big yachts and boats pass by on the...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Private Tropical Paradise in Holmes Beach!  Large home with Pool and fenced yard1 / 25
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Grill
    • Wi-Fi
    • Patio
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 April 2018
    We stayed at this house for 2 weeks. There’s a lot of room inside. House is well stocked with towels and any utensil you need. It is close to everything and the neighborhood is...
    Reviewed 21 March 2018
    Anna Maria Island is a friendly, eclectic place to visit. This is a very nice home with a fenced in yard and pool. It worked very well for our dogs and us!
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    About this property
    Tropical Paradise on Holmes Beach and ONLY 3 blocks to the beach. Anna Maria Island, noted for its old Florida ambiance, offers this Key West styled home, where you may awaken to greet the dawn sipping coffee on the balcony or swimming in your private pool. The modern interior arrangements add to...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
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    Sand Castle well appointed home steps from beaches1 / 25
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Grill
    • Private Outdoor Pool (Heated)
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 August 2017
    My family stayed in this home August 2016. The home is beautiful and we enjoyed our stay very much. The home was well equipped and pretty clean. I did has a couple issues at...
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    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...
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Anna Maria Island #2 Beachside Palms1 / 17
    (3)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Ocean Views
    • Housekeeping Included
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 May 2018
    The Rental was very relaxing, clean and easy to find. Location to the beach was excellent. The deadbolt lock was broken, this was unfortunate as one night someone was outside...
    Reviewed 24 February 2017
    Excellent spot. Immaculate. Close to beach (3 minute walk), Publix, Walgreens and CVS. Owner (Jerry) is super nice to deal with. You can book directly from Property...
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    About this property
    Beachside Palms Anna Maria Island Resort is extremely conveniently located directly across from the famous Manatee County Public Beach on the gorgeous Gulf of Mexico. All 3 of our units were completely updated in 2016. They feature new cabinets, stainless steel appliances and granite countertops....
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Casa Playa East is a Luxury 4 bedroom home with a pool and elevator!1 / 33
    (2)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Washer
    • DVD Player
    • Ocean Views
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 October 2017
    We booked our stay here for our family (6 adults, 2 kids) totally unfamiliar with Anna Maria Island, coming for a wedding at a nearby venue. We couldn't have been happier...
    Reviewed 8 August 2015
    We rent a home in Anna Maria every year. Hands down, for my active group, this is the best location. Two blocks from hopping Bridge Street. Beach access 1/2 block away. Bay...
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    About this property
    This Bradenton Beach vacation home provides you and your family or small group with your very own private swimming pool, and comes fully equipped with everything you need for a wonderful vacation on this beautiful barrier island. Your accommodations are less than 1/2 block from the beach and 1...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    White House Vacation Apartments1 / 15
    (7)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Reviewed 4 weeks ago
    This was a great place to stay. Clean and I’m a great location. Neighborhood was quiet and safe. Terri was a great host Check in and out was easy. We will definitely be...
    Reviewed 4 October 2017
    My family and I and of course our family dog were welcomed with open arms. The apartment was very roomy and comfortable and had all the comforts of home with full size...
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    About this property
    Just half a block to the beach and steps to our fishing dock on Sarasota Bay, these cute and cozy apartments offer a great vacation value on Anna Maria Island. Watch the sunrise from the dock every morning and cap your busy day with sunset over the Gulf of Mexico. White House Vacation Apartments...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    The Tree House1 / 22
    (6)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Grill
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 March 2018
    We had a family of 6 of us stay last week, had everything we needed there. it was close to the beach! It was clean and had ample room for us all to sleep. We would definitely...
    Reviewed 5 July 2017
    Nice quiet location Has everything you need. We enjoyed our stay and would come back. Easy access. Clean!
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    About this property
    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....
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Anna Maria Island Nantucket1 / 29
    (23)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 January 2018
    My extended family stayed here this past December, and it was perfect. The place is showing it's age a bit, and there is a rather steep set of stairs to get to the main floor...
    Reviewed 10 April 2017
    We rented this home over Spring Break with my brother and his family. The layout of this house is great as well as the location of the home on the island. There were 2 master...
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    About this property
    3 Story 'Nantucket' Style - 4 bedroom/ 3 bath villa is just a short walk to the beach - Nestled in a tropical setting, only a few blocks to the Gulf beach; heated private pool great for cooling off and a large sun deck. 4 Bedrooms/3 baths, large master suite with king size bed and a roman tub,...
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Cast Villa 31 / 24
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Private Garden
    • Parking
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Cast Villa sits in the heart of Anna Maria Island directly across from the famous Manatee County public beach W/life guard which features a gift/surf shop, restaurant, Tiki bar, live music and more. Beach is groomed daily and has lifeguards. Walk to Publix grocery store, CVS drug store and...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    On the Beach Paradise d1 / 13
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Ocean Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 July 2018
    We had such an amazing time at Mike's place. We rented the downstairs unit... it was right on the beach. It was clean and had everything we needed. Lots of stores are walking...
    Reviewed 30 January 2018
    Steps to the beach with lots of beach seating. A great outside dining area complete with grill. Our only problem was finding a comfortable bed. Some people like the foam...
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    About this property
    This cottage is located 'on the beach' 3007 Avenue F, beautiful Holmes beach. It is the downstairs unit (1 of 2). The cottage is very comfortable and sleeps 4 comfortably with additional space for a pull-out. This quaint cottage is hidden away on a dead end street, away from it all yet close...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • Wi-Fi
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Ocean Views
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bay view Home, located at 404 21st Place in Bradenton Beach is a hidden treasure! This wonderful home features 4 bedrooms and 3 bathrooms on a quiet street ending at the water. Best of all, this beautiful home is canal front with beautiful views of the bay! It features a private heated pool, BBQ...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Housekeeping Included
    • Ocean Views
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beachside Palms Anna Maria Island Resort is extremely conveniently located directly across from the famous Manatee County Public Beach on the gorgeous Gulf of Mexico. All 3 of our units were completely updated in 2016. They feature new cabinets, stainless steel appliances and granite countertops....
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Patio
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the SS Salamander located at 121 50th Street in Holmes Beach. This recently updated duplex is just a one block stroll down a side street to the beautiful white, sandy beaches. It’s located in a quiet and preferred residential neighborhood yet it's easily within walking distance to...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Parking
    • Patio
    • Grill
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Alamanda Villas, located at 102 39th Street in Holmes Beach is a charming beachside complex featuring eight units surrounding a heated pool, tropical landscaping, multi-level decks and built in BBQ area. Anna Maria's white sandy beaches and the emerald green water of the Gulf of Mexico are just...
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    Holmes Beach, Anna Maria Island 34218
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
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    • Private Garden
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cast Villa #4 is the most private on this lush tropical Half acre property. Located directly across from the famous Manatee County Pubic Beach. Swim with Life guards present. Known for the pristine sugar white sand beaches. Dine early breakfast or have a beverage listening to live music daily....
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    104 75th Street, Holmes Beach, Anna Maria Island Wonderful 1 bedroom townhouse apartment located just steps to the beach. This tasteful apartment is the 'guest quarters' to the main house. Built in the 1940's and transformed into a vintage and eclectic getaway. Decorated with antiques and...
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Casa Playa - Combo1 / 52
    (3)Very good
    8 Bedrooms, 8 Bathrooms, Sleeps 20 Quick View
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    • Cable/satellite TV
    • Washer
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Patio
    • DVD Player
    • Ocean Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 January 2015
    We stayed at Casa Playa for the week after Christmas over New Years! The location is amazing...close to everything you need except a grocery store. The weather was perfect, the...
    Reviewed 10 April 2014
    We stayed here for the full month of March and very much really liked this unit. The owners ( Scott Deb ) were very nice, as they were wanting to make sure we had everything we...
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    About this property
    This Bradenton Beach vacation home is actually two rentals in one, in the middle of all the fun and beaches that Bradenton Beach can offer. The rental package sleeps up to 20, and everyone can enjoy the 2 private swimming pools. This is a fully equipped rental home on Anna Maria Island, with...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 20
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A Wright Place, located at 6803 Holmes Blvd., is a comfortable two bedroom, two bath duplex with poolside den which can easily serve as a third bedroom. It's exactly what you are looking for in a peaceful Anna Maria Island retreat. Located in a quiet, lakeside residential neighborhood, this unit...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ss Salamander North1 / 21
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Patio
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 June 2017
    We truly enjoyed staying here. It's within great walking distance to the beach. The kitchen was fully stocked with almost anything you can think of and they also had plenty of...
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    About this property
    Welcome to the SS Salamander, North unit at 121 50th Street in Holmes Beach. This recently updated two bedroom and one and one half bath unit is just a one block stroll down a side street to the beautiful white, sandy beaches. It’s located in a quiet and preferred residential neighborhood yet it's...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come discover 'Paradise Cottage' with all it's old Florida charm as well as newly updated appliances and decor.  This lovely and colorful two bedroom, two bath home feels brand new.  You'll enjoy tile floors throughout, a large eat-in kichen, comfortable and attractive furnishings with an updated...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Amazing beachfront Studio on Bradenton Beach, Anna Maria Island. Step out your door and your feet are in the sand. I doesn't get any better than this. This small studio has everything you need to enjoy your time in the Florida Sunshine. Many restaurants and shops nearby and even take the...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Grill
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    • Cable/satellite TV
    • Washer
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Beach Breeze Hideaway! This cute island property is just perfect for your laid-back Anna Maria Island retreat! Newly updated throughout, this 2 bedroom/2 bathroom beach duplex is just a short walk  to the fabulous Gulf beaches of Anna Maria Island! The living area is spacious...
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    Location Information
    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Anna Maria Island #3 Beachside Palms1 / 12
    (1)Terrible
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Central Heating
    • Washer
    • Grill
    • Housekeeping Included
    • Patio
    • Ocean Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beachside Palms Anna Maria Island Resort is extremely conveniently located directly across from the famous Manatee County Public Beach on the gorgeous Gulf of Mexico. All 3 of our units were completely updated in 2016. They feature new cabinets, stainless steel appliances and granite countertops....
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    Location Information
    Holmes Beach, Anna Maria Island 34209
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Grill
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    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Azure Seas is a glorious three bedroom, two bath Gulf front home located at 779 North Shore Drive in the much desired and tranquil northern end of Anna Maria Island. Tropical paradise found!! This is the perfect place to forget your troubles and soak in the unbelievable views of the Gulf of...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
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    • DVD Player
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunseeker Haven located at 302 24th St North Unit B in Bradenton Beach is a light, bright upscale two bedroom two bathroom vacation getaway. It is nestled between beautiful Anna Maria Sound and the turquoise Gulf waters. Enjoy the entire spacious upper floor of the two unit condo. You have French...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    BAY FRONT HOUSE WITH PRIVATE DOCK1 / 17
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Private Garden
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    House was perfect for the 2 of us plus 17 yoa son and dog. Walking distance to a couple of great restaurants and beach was about 2-3 min walk. Fished off the dock nearly every...
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    About this property
    Two Bedroom/2bath Home in Bradenton Beach Sleeps 6. This is a two bedroom/2bath home in Bradenton beach, with washer/dryer, new kitchen (granite counters), big screen/WiFi, great fishing on your own dock, on a quiet street, five minute walk to bridge street shopping area, two minute walk to the...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    Sunset View is a three bedroom, two bath home located at 100 7th Street South in Bradenton Beach. This home has been totally renovated and features a large heated pool. Sunset View is directly across the street from a wide expanse of beach – no houses, just beautiful water views! It's a perfect...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled on the far north end of Anna Maria Island, three houses from beach access, is The Lady Fish, a newly remodeled three bedroom, two bathroom vacation home. Guests will enjoy a full gourmet kitchen with gas oven, cook top and ice maker, perfect for mid-day snacks and cooking up your catch...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pet friendly
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    Smoking allowed
    About this property
    The Anna Maria Escape located at 725 North Shore Drive in Anna Maria city is just that - a peaceful, relaxed place to get away from it all. You can stroll on the beach for miles in either direction! It’s a perfect Anna Maria Island vacation home! This spacious and charming two bedroom, two...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Siboney located at 3700 Gulf Drive in Holmes Beach, is an exquisite, executive level home with a private heated pool set amidst tropical, native landscaping. Its 2000 square feet of luxury! The beach is approximately one half block away with no major roads to cross. You can enjoy views of the...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Ocean Views
    • Washer
    • Shared Outdoor Pool (Unheated)
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pelican Cove Condominium, located at 901 Gulf Drive South in Bradenton Beach offers it all! This smaller complex features full bay views, boat dock, heated pool, spa and tennis. There is a large, screened lanai where you can enjoy your morning coffee while watching the sunrises. Located close to...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Alamanda Villas, located at 102 39th Street in Holmes Beach is a charming beachside complex featuring eight units surrounding a heated pool, tropical landscaping, multi-level decks and built in BBQ area. Anna Maria's white sandy beaches and the emerald green water of the Gulf of Mexico are just...
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    Holmes Beach, Anna Maria Island 34218
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Alamanda Villas, located at 102 39th Street in Holmes Beach is a charming beachside complex featuring eight units surrounding a heated pool, tropical landscaping, multi-level decks and built in BBQ area. Anna Maria's white sandy beaches and the emerald green water of the Gulf of Mexico are just...
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    Holmes Beach, Anna Maria Island 34218
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Sweet Escape is located at 111 4th Street South in Bradenton Beach. If you want to have the best of both worlds on Anna Maria Island, look no further. This beautiful beach property is located right in the middle of everything! It’s just three houses from either the beach or bay. Historical...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to this charming, dog-friendly Anna Maria Island house. With the private heated pool and hot tub, you will feel like you're miles away from your worries. There is a large, fenced-in backyard with lush landscaping, where you can soak up the warm island sun from a pool-side lounge chair....
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Valhalla located at 3216 Gulf Drive in Holmes is a wonderful five bedroom, three bath Gulf front duplex on a secluded beach. While the Valhalla is tucked away in a quiet area, it is within walking distance to shopping and restaurants. The location is perfect! Each unit features a large...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 13
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Beach House Resort #9, located at 1000 Gulf Drive in Bradenton Beach is in a totally renovated gulf front complex. The white, sandy beach stretches for miles in either direction! It features a large, private spa and spectacular beach views from virtually every room. Unit 9 even has a view of...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Patio
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Valhalla upstairs unit, located at 3216 Gulf Drive in Holmes is a wonderful three bedroom, two bath Gulf front duplex on a secluded beach. While the Valhalla is tucked away in a quiet area, it is within walking distance to shopping and restaurants. The location is perfect! The large...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Pool Party North side, located at 314 61st Street in Holmes Beach, is a beautiful two bedroom, two bath duplex with a pool area that is unsurpassed! This unit features a heated pool with a spa surrounded by mature, native plantings as well as a shaded hammock and an outdoor bar with charcoal...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is a ground level private home with five bedrooms, three full bathrooms, and private heated pool. One of the best values on the island with so much to offer! The bedrooms are perfectly situated with three on one end and two on the other. This house has been completely remodeled and...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Coco Cabana located at 309 A 58th St in Holmes Beach is a beautiful three bedroom two bathroom home with a private heated pool. This ground-level home has everything you could want, just a few blocks to the beach, and close to shopping and dining. After a day at the beach come back and continue to...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Bay Breeze, located at 402 20th Place North, is a lovely, two bedroom and two bath canal front home with a new large deck, boat dock and davits. It has undercover parking and a large screened lanai overlooking the natural canal. There is a gas grill on the new deck. This is a perfect home for...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Balcony
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    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our property is located on beautiful Anna Maria Island on Florida's Central Gulf Coast, at the entrance to Tampa Bay, and offers the finest in Florida Gulf Coast vacation rentals and area real estate sales. We feature rental homes and condos on Holmes Beach, Bradenton Beach and the City of Anna...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Valhalla downstairs unit, located at 3216 Gulf Drive in Holmes is a wonderful two bedroom, one bath Gulf front duplex on a secluded beach. While the Valhalla is tucked away in a quiet area, it is within walking distance to shopping and restaurants. The location is perfect! The large...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Cable/satellite TV
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Bman Beach Cottage located at 2812 Avenue B in Holmes Beach is a cute 2 bedroom 2 bath private home. This ground level home has two screened lanais one overlooking the pool and Jacuzzi. The kitchen has been newly updated as well as one of the bathrooms. This property has long distance and WiFi...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Seagrass Flats Condo #3 is a upper level, pool side unit located at 101 25th Street North in Bradenton Beach. It is a four unit complex located near one of the widest beaches on the island and features a heated pool and barbeque area. Immediately across from the beach, you can be on the sand in...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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