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Holiday Rentals in Anna Maria

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    Travellers to Anna Maria are booking December dates now. Secure your holiday home today, and have the perfect trip.
    All 217 Rentals in Anna Maria
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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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    Crescent Wave1 / 120
    (24)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Patio
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    • Cable/satellite TV
    • Balcony
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Skimmer unit at the Blue Dolphin Inn, located at 404 Alamanda in the Historic Village of Anna Maria is a wonderful two bedroom, one bath downstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with fountains and nearby tiki...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    5 Star - Private Pool & Dock, and Steps Away from the Beach - Fall Availability1 / 39
    (5)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    • Waterfront
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2017
    The house was gorgeous. Pretty and comfortable furnishings. Loved all the Anna Maria touches. Fantastic kitchen appliances - I wish my washing machine was so good! We all loved...
    Reviewed 28 October 2016
    We had a fantastic time exploring Anna Maria Island and coming home to such a fantastic place made the holiday even more special.
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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...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Cast Villa 11 / 31
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Grill
    • Washer
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 August 2017
    Was absolutely wonderful. Couldn't ask for better vacation. Very close to beach. Unit had everything we needed. Owner was very friendly and accomidating. Will definately be back.
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    About this property
    Anna Maria Island, This property is located directly across from the famous Manatee County Public Beach. Groomed daily, Lifeguards, restaurants, surf shop and more.. Free trolley stops there both northbound and south every 20 minutes. The location is also right in the heart of the island. Walk to...
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Terrace
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    742 Jacaranda- Single Family home 3 bedrooms/ 2.5 baths, maximum occupancy of 6 people. Distance to the Beach: 50 yards This well appointed home has recently been renovated. The balconies have all been redone, new stairway and all new furniture in the living room and bedrooms The master bedroom...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    744 Jacaranda Rd1 / 32
    (9)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Terrace
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 May 2013
    We loved this house for the week we spent in it. it was very clean and had all the little extras that make a holiday let in the U.S. ideal for a U.K. family - i.e. lots of beach...
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    About this property
    744 Jacaranda - Private home 3 Bedroom/ 3 Bath with private pool, maximum occupancy of 6 people. Distance to the Beach: 1 1/2 block Rates just reduced!! Book your holiday getaway today. $200 off any booking for the first two weeks in December 2018. Exclued the Holidays.(December 22, 2018 -January...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Blue Heron Waterfront House Anna Maria island1 / 23
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Ocean Views
    • Washer
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 June 2017
    We stayed for a week at the end of May 2017 after spending 10 days in Orlando. We were met at the property (even though we were a little late) and it was beautifully presented...
    Reviewed 22 May 2017
    The location is perfect. Walk 2 blocks to beach. Supermarket, drug store, bank, restaurants, salon, spa, less than 5 min. away. Many choices to dine/shop 3-10 min drive. The...
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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...
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 3 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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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Ocean Views
    • DVD Player
    • Central Heating
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    • Patio
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    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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Terrace
    • DVD Player
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    209 Spring - Private home 3 Bedroom / 2 Bath with private pool, maximum occupancy of 8 people. Distance to the Beach: 1 Block Spring into the waves!~ 209 Spring. 3 bedroom, 2 bath raised home in quiet, residential area of Anna Maria. Private pool. Pool heat optional * $20/day. 1 block to...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Patio
    • Balcony
    • Washer
    • Private Outdoor Pool (Unheated)
    • Terrace
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Manatee Cottage is a newly remodeled two bedroom, two bathroom private home with a pool and spa. This fabulous house is only a short walk to the white sand beaches of Anna Maria and also a short walk to Bay Front park.  Stroll down to Pine Avenue and dine out at one of the many fine...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Charming 2 Bedroom/2 Bath Cottage on a Canal1 / 22
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Grill
    • Washer
    • DVD Player
    • Central Heating
    • Hot Tub
    • Waterfront
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    We thoroughly enjoyed our stay at this lovely cottage located on the northern tip of Anna Maria Island. The home is charming and well-cared for. The shaded yard was on the...
    Reviewed 26 April 2017
    I loved that the owner went our of her way to reserve pack and plays for our two little ones. They had everything for beach trips including a wagon, beach toys, and umbrellas...
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    About this property
    Our 2 bed/2 bath cottage is the perfect home to spend your vacation. Located on a canal, you can bring your boat or rent kayaks. Fishing is great from the dock. House and yard is very private. Soak in the jacuzzi after a long day at the beach or relax in the hammock. We have 2 bikes, beach...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Sauna
    • Washer
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Marisol, located at 797 North Shore Drive at the north end of Anna Maria Island and nestled on the shores of the Gulf of Mexico, offers breathtakingly beautiful views of the crystal blue waters of the gulf. This is unquestionably one of Anna Maria's loveliest homes. This spectacular home...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Charming cottage w/ island views, entertainment & nearby beach access!1 / 33
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • Internet Access
    • Patio
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    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    If your looking for a laid back beach cottage in a laid back beach community this is it. Little delay getting in the door because the key pad didn’t work, but once I stepped...
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    About this property
    A dose of sunshine and relaxation awaits you at this comfortable cottage on Anna Maria Island, featuring island views, entertainment, and easy access to the beach. Located immediately east of Gulf Drive, a quick 200-yard walk will bring you right to the white-sand beach and crystal-clear waves. Go...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Beach to Bay Getaway! Anna Maria Island was a quaint historic fishing village and has become one of the top travel destinations by travelers from around the world. Known for world class beaches, top rated restaurants, fishing/boating and laid back stmosphere. This...
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    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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    • Internet Access
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    7201 Palm Drive, Holmes Beach, Anna Maria Island Palm Cottage ... Lovely 2 bedroom, 2 bath recently updated home. This ground level home offers a beachy decor, a new pool , granite countertops, and a great screened in porch. Just a short walk to the beach. Pool heat is additional....
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, 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
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    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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Flamingo unit at the Blue Dolphin Inn, located at 780 Jacaranda in the Historic Village of Anna Maria is a wonderful and spacious three bedroom, two bath upstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with fountains...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    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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    Anna Maria, Anna Maria Island 34216
    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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    • Wi-Fi
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    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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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    9 Bedrooms, 6 Bathrooms, Sleeps 26 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Blue Dolphin Inn, located at 780 Jacaranda and 404 Alamanda in the tranquil City of Anna Maria features four units surrounding a tropical heated pool with tiki huts, grills, rooftop observation decks and loads of charm. Each unit has its own private patio and charcoal grill for an evening of...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 9 Bedrooms, 6 Bathrooms, Sleeps 26
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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
    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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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Grill
    • Balcony
    • Washer
    • Patio
    • Private Outdoor Pool (Unheated)
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Deja Vu is just a short stroll to the beautiful beaches of Anna Maria!  This gorgeous home is a 3 bedroom 3 bath with a private heated pool. The pool area is very inviting with the sun on it throughout the day.  After a long day at the beautiful beaches of Anna Maria freshen up with the...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    BEACHFRONT HOME, TRUE PARADISE , DOGS STAY FREE, GREAT VIEWS, WALKING BEACH1 / 22
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 November 2017
    Awesome pet friendly beach house right on the water. It has amazing views of the Sunshine Skyway bridge and we enjoyed watching the boat traffic in the distance! So relaxing...
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    About this property
    This stunning BEACHFRONT home was designed by an award winning Architect and is true paradise. The plan is open with the Living, Dining, Kitchen and Master Bedroom on the Waterfront adjacent to the deck which runs the entire length of the home. The elevated deck is a mere 10' from the waters edge....
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Washer
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    • Grill
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The desirable North end of Anna Maria and a peaceful canal front setting make this beautiful home a perfect vacation getaway! Gladiolus on the Water was recently updated with new furnishings and fresh paint, all tied together with a festive and tropical theme! With a comfortable couch and...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Patio
    • Private Outdoor Pool (Unheated)
    • Washer
    • Terrace
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tarpon Pointe is a gorgeous newly remodeled 2 bedroom 2 bath island home located on the north end of Anna Maria Island. You’ll enter the home from a large front deck with sliding glass doors into the living area. The living area features a large 65 flat screen HDTV with plenty of seating for the...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Grill
    • DVD Player
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    • Balcony
    • Washer
    • 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 6 Quick View
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    • Patio
    • Wi-Fi
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Washer
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Heron unit at the Blue Dolphin Inn, located at 404 Alamanda in the Historic Village of Anna Maria is a wonderful two bedroom, two bath upstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with fountains and nearby tiki...
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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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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • DVD Player
    • Terrace
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Brand New Rental!   Sea Haze is a mere 212 steps to the beach and the crystalline gulf! As you take your short walk to the gulf beaches, you will take in the sights of the dense banyans, spectacular homes of Park Avenue and the tropical sea grapes. Sea Haze is perfectly located - west of Gulf...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    19 Palms. Quaint Old-Florida Charm1 / 23
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Secure Parking
    • Wi-Fi
    • Private Garden
    • Washer
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 March 2018
    My husband and I come to Anna Maria Island annually and always stay here. It’s spotless, beautifully decorated, ultra comfortable beds and new shower heads. The location...
    Reviewed 4 March 2018
    The location of the house is close to the beach and you can also walk to all the shops and dinning or bike ride. Parking is right at the doorstep and it is on a quiet street...
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    About this property
    This quaint, old-Florida style rental is nestled in the north shore area of Anna Maria Island. Shabby chic style, located 2 blocks from the beach and 2 blocks from the bay! Only one block from Pine Ave., with its old-time feel with shops and salons. Steps from fine dining, the historic city pier,...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
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    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the Pier House! What a location and north of Pine Avenue! An old style florida three bedroom/two bathroom cottage on the north end of the Island! Pier House is right around the corner from the Rod and Reel Pier where you can enjoy the famous grouper sandwich. The Cottage is a short walk...
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Balcony
    • Washer
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled right in the midst of Anna Maria Island is this 3 bedroom 2 bath single family home with private pool. The pool area is very inviting with sun on it throughout the day... Enjoy evening cocktails in the large screened in poolside patio. Enjoy a hot outside shower when you get home from the...
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    Location Information
    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Grill
    • Cable/satellite TV
    • Parking
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    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, 2 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Flamingo unit at the Blue Dolphin Inn, located at 780 Jacaranda in the Historic Village of Anna Maria is a wonderful and spacious three bedroom, two bath upstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with fountains...
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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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    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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    9 Bedrooms, 6 Bathrooms, Sleeps 26 Quick View
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    • Central Heating
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Blue Dolphin Inn, located at 780 Jacaranda and 404 Alamanda in the tranquil City of Anna Maria features four units surrounding a tropical heated pool with tiki huts, grills, rooftop observation decks and loads of charm. Each unit has its own private patio and charcoal grill for an evening of...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 9 Bedrooms, 6 Bathrooms, Sleeps 26
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lime In De Coconut- Downstairs. Adorable, ground level two bedroom, two bath in a 2 unit cottage. Cheery beach decor and a shared heated pool in a tropically landscaped courtyard. This unit also offers a screened lanai, flat screen TVs, wireless internet access, washer & dryer, dishwasher and a gas...
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    Location Information
    Anna Maria, Anna Maria Island 34217
    Cabin Holiday Rental - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lime in De Coconut - Upstairs..... Adorable, one bedroom, one bath in a 2 unit cottage. Cheery beach decor and a shared heated pool in a tropically landscaped courtyard. Flat screen TV, wireless internet access, washer & dryer, and a gas grill (propane is guest's responsibility). Located just a...
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    Location Information
    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Terrace
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    • Grill
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    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minnow 2  is a ground level, beautiful, tastefully decorated, polished terrazzo throughout, two bedroom, one bathroom bungalow offering a secluded and private screened in patio! It is only a short 2 minute stroll over to the beautiful white sandy beaches and a 45 second walk to the Rod and Reel...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Seagull Way!  This beautiful designer home is on Bimini Bay.  Seagull Way is a well appointed 4 bedroom/4 bath home that is comfortably furnished.  Sit back and relax in the high quality formal living room and dining room with luxurious furniture.  Enjoy a quiet night watching a movie in...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Heron unit at the Blue Dolphin Inn, located at 404 Alamanda in the Historic Village of Anna Maria is a wonderful two bedroom, two bath upstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with fountains and nearby tiki...
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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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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
    • Grill
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Ibis unit at the Blue Dolphin Inn, located at 780 Jacaranda in the Historic Village of Anna Maria is a wonderful two bedroom, one bath downstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with fountains and nearby tiki...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Brand New Renovation Sea Waves Cottage1 / 16
    (8)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Waterfront
    • Patio
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 April 2018
    My wife and I stayed at this nice, updated rental and really enjoyed our time. The location was great, with a deck right on a canal. We were walking distance to the beach.The...
    Reviewed 23 March 2018
    The beach house was awesome!!! Had everything we needed. It was true to the pictures on line. Jenny the owner was awesome, got back to we when I had questions right away. We...
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    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...
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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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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Central Heating
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Skimmer unit at the Blue Dolphin Inn, located at 404 Alamanda in the Historic Village of Anna Maria is a wonderful two bedroom, one bath downstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with fountains and nearby tiki...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Central Heating
    • Grill
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    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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Terrace
    • Washer
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Sea Mist! his beautiful 3 bedroom 2 bathroom property has 1,742 square feet of living space and the ability to accommodate 6 guests very comfortably inside and out. From the quality quilts and linens on the beds, to TV's in the living room, Master bedroom, and the fully...
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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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Central Heating
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    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 bath...
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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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