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Vacation Rentals near Anna Maria City Pier

100 S Bay Blvd, Anna Maria, Anna Maria Island, Florida 34216
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    Travelers to Anna Maria are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    All 239 Rentals in Anna Maria
    19 Palms. Quaint Old-Florida Charm1 / 23
    (4)Excellent
    0.2 miles from Anna Maria City Pier
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Beachfront Paradise w/ Private Beach, Dogs Stay Free, Beach in Backyard1 / 42
    (9)Excellent
    0.2 miles from Anna Maria City Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Gorgeous views,spectacular home!1 / 49
    (37)Very good
    0.3 miles from Anna Maria City Pier
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    'Island Oasis'  A single family North end canal home with pool1 / 68
    (2)Excellent
    0.2 miles from Anna Maria City Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Washer
    • Air Conditioning
    • Waterfront
    • DVD Player
    • Ocean Views
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 14, 2018
    The location is amazing for boats/jet skis. The house is perfect for up to two families with two master suites and an additional half bath. The kitchen is well-equipped with...
    Reviewed September 30, 2015
    I chose Island Oasis as it ticked every box. This is a beautiful island and the beach is very easy to access, as such I wanted a property with a pool, suitable for two couples...
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    About this property
    Step into an ultra private, secluded, tropical paradise with a lush canal front setting in quiet cul-de-sac located on the north end of Anna Maria Island. There is a beautiful heated pool just steps outside your door. The back yard has multiple areas to relax away the day and enjoy the amazing view...
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    Anna Maria, Anna Maria Island
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Charming 2 Bedroom/2 Bath Cottage on a Canal1 / 22
    (3)Excellent
    0.2 miles from Anna Maria City Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
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    • Central Heating
    • Hot Tub
    • Waterfront
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 16, 2019
    We stayed here for 4 nights in May and I must say I was surprised at how nice this place was. It’s in a great location for local amenities but still really private which was...
    Reviewed August 2, 2018
    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...
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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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    0.2 miles from Anna Maria City Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Shared Outdoor Pool (Unheated)
    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 a brand new mastersuite. Enjoy new furnishings and fresh paint, all tied together with a festive and tropical theme! The...
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    Anna Maria, Anna Maria Island
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    0.2 miles from Anna Maria City Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully renovated beach cottage in the heart of the village of Anna Maria. Walk to the beaches, shops and restaurants. Enjoy amazing sunsets at the beach or sip a glass of wine in the lush tropical gardens surrounding the cottage. 2 bedrooms with 2 full bathrooms. Quaint beach cottage in a...
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    Anna Maria, Anna Maria Island
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.3 miles from Anna Maria City Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Welcome to Gladiolus House! What a location, North of Pine Avenue with a glimpse of the Bay! This old style Florida two bedroom/two bathroom cottage on the north end of the Anna Maria Island offers ground level living. Enjoy Island life and all the best of Anna Maria without the North end prices!...
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    Anna Maria, Anna Maria Island
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    0.3 miles from Anna Maria City Pier
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    • Hot Tub
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful luxury beach front condominium for rent for the first time. There's only 2 condo's on the entire property. This condo is 3500 square feet including gourmet kitchen, dining room, living room with fireplace and built in flat screen TV. screened in lanai overlooking the Gulf of Mexico, den...
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    Anna Maria, Anna Maria Island
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    0.3 miles from Anna Maria City Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Haupia House is a newly remodeled two bedroom, two bathroom elevated canal front home with a pool, spa and a new boat dock in the city of Anna Maria. This fabulous house is only 2 short blocks to the white sand beaches of Anna Maria Island and a short walk to the restaurants and shops on Pine...
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    Anna Maria, Anna Maria Island
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Gulf Front Guest House1 / 15
    (3)Very good
    0.5 miles from Anna Maria City Pier
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
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    • Terrace
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    Pet friendly
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    Smoking allowed
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    Anna Maria, Anna Maria Island
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    0.2 miles from Anna Maria City Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    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 restaurants....
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    Anna Maria, Anna Maria Island
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.2 miles from Anna Maria City Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Smoking allowed
    About this property
    LOWER RENTAL RATES! Take advantage while it lasts! Bird of Paradise is a newly remodeled two bedroom, two bathroom, home north of Pine Avenue in the City of Anna Maria. Enjoy easy Island life surrounded by tropical landscaping. It sleeps up to 4 guests. The open floor plan streamlines the living...
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    Anna Maria, Anna Maria Island
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    0.2 miles from Anna Maria City Pier
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    **THE CITY OF ANNA MARIA HAS ISSUED AN ORDER OF A 30 DAY MINIMUM RENTAL FOR NEW RESERVATIONS THROUGH JUNE 30, 2020.** Manatee Manor is a newly remodeled two bedroom, two bathroom, pool, and canal front home in Anna Maria. Enjoy easy Island life surrounded by tropical landscaping and a sailboat...
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    Anna Maria, Anna Maria Island
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 6
    0.1 miles from Anna Maria City Pier
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly Renovated Bathrooms and Fabulous New Flooring and up-dates throughout the whole property! Welcome to Canario Cottage! This beautiful 3 bedroom, 3 bathroom property has 1254 square feet of elevated living space and the ability to accommodate 6 guests very comfortably inside and out. Canario...
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    Anna Maria, Anna Maria Island
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    0.2 miles from Anna Maria City Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Island Priva-Sea! If it is privacy you are looking for you will get plenty in this North-end island house. Tucked away in a cul-de-sac the location North of Pine Ave and a peaceful canal front setting make this beautiful home a perfect vacation getaway! Island Priva-Sea has a convenient...
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    Anna Maria, Anna Maria Island
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    0.3 miles from Anna Maria City Pier
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    • Shared Outdoor Pool (Unheated)
    • Parking
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    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Lazy Hammock! This amazing north-end canal front home has everything you need to make this your best Anna Maria Island vacation ever. Park your car in the circular drive, enter through a jasmine pergola to this stunning ground level beach house and never leave! The vacation home is...
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    Anna Maria, Anna Maria Island
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    0.2 miles from Anna Maria City Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Wi-Fi
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spring Haven This lovely island home, newly built, is a perfect place to spend your family vacation. Its spacious layout is complemented with island decor and modern amenities, from brand new appliances in the kitchen to large, flatscreen tv's. When not enjoying the comfortable interior take a...
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    Anna Maria, Anna Maria Island
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Bay-facing condo w/amazing view, shared pool & beach across street1 / 36
    (1)Excellent
    0.0 miles from Anna Maria City Pier
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Smoking allowed
    About this property
    South Bay Inn 2 This spacious condo with spectacular views of Tampa Bay offers wonderful access to some of the best attractions in Anna Maria! Located right across the street from the beach and the bayshore, this property comes equipped with a shared swimming pool, a full kitchen, a game table for...
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    Anna Maria, Anna Maria Island
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    0.3 miles from Anna Maria City Pier
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Hibiscus House! This is a four bedroom, three bathrom vacation rental home which is spacious and family friendly. Located directly across from the Bay with views of the Intercoastal waters and children's playground, you'll love this location. It's a few minutes walk to the Rod 'n Reel...
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    Anna Maria, Anna Maria Island
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    0.3 miles from Anna Maria City Pier
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Beach to Bay Getaway This Anna Maria home is a great place to spend your island time. Spread out in the living room includes that features a 48' flat screen TV and BlueRay player which include Netflix and Hulu Plus access (need your own login). The house is nicely equipped with everything from...
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    Anna Maria, Anna Maria Island
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    0.1 miles from Anna Maria City Pier
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    South Bay Inn 1 This romantic getaway is a great place to spend some time on Anna Maria Island. Located right across the street from the bay, this rental is just a short stroll from the beach! It comes with a shared pool and comfortable outdoor furniture for relaxing in the island breeze. What's...
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    Anna Maria, Anna Maria Island
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    0.1 miles from Anna Maria City Pier
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    South Bay Inn 3 This condo's location makes it a great place for a romantic getaway on Anna Maria Island. Situated right across the street from the bay, this property puts the beach just a short walk away! It comes equipped with great amenities including a shared pool, an updated, full kitchen,...
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    Anna Maria, Anna Maria Island
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    0.3 miles from Anna Maria City Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Mon AMI Beach House Welcome to your new vacation home away from home on Anna Maria Island! Offering four parking spots and a private, pristine pool, this home is perfect for the whole crew to come enjoy! Located on bustling Pine Avenue, you’ll be in the heart of Anna Maria's shopping, dining,...
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    Anna Maria, Anna Maria Island
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    0.1 miles from Anna Maria City Pier
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Welcome to Bodacious Oasis! This beautiful 4 bedroom 2 and 1/2 bath property can accommodate 8 guests very comfortably inside and out. Larger families will enjoy the open floor plan, providing plenty of room to spread out and enjoy comfortable island style furnishings and entertainment features....
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    Anna Maria, Anna Maria Island
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    0.2 miles from Anna Maria City Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Waterfront
    • DVD Player
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    Pet friendly
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    About this property
    Grant's View You'll be able to spot this adorable mint-green bungalow from down the street! This charming home's dazzling location backs up to the bay with wide-open views of the waves. Keep an eye out for dolphins from your deck or bring a book out to the beach chairs and stick your toes in the...
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    Location Information
    Anna Maria, Anna Maria Island
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Vacation Home with pool/canal front/3 blocks to Gulf beach on Anna Maria Island1 / 16
    (34)Excellent
    0.4 miles from Anna Maria City Pier
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Anna Maria, Anna Maria Island
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Gulf front, charming home right on the beach - stunning views & dogs welcome!1 / 30
    (75)Excellent
    0.5 miles from Anna Maria City Pier
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Anna Maria, Anna Maria Island
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    $200  towards a private fishing charter with Captain Josh with 2020 reservation1 / 18
    (50)Excellent
    0.2 miles from Anna Maria City Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Anna Maria, Anna Maria Island
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Tucked Away 7165506 - Bungalow Bobs1 / 50
    (32)Excellent
    0.4 miles from Anna Maria City Pier
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Anna Maria, Anna Maria Island
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Reduced Rates 25% OFF! 30 Second Walk to the Gulf Beaches! Heated Pool1 / 34
    (1)Excellent
    0.7 miles from Anna Maria City Pier
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Anna Maria, Anna Maria Island
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 8
    *Fall Specials* New Luxury-Prof. Decorated Pool/Spa 5 Minutes walk to beach1 / 36
    (15)Excellent
    0.5 miles from Anna Maria City Pier
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Anna Maria, Anna Maria Island
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Waterfront home near beaches with private pool, spa, and more!1 / 50
    (28)Excellent
    0.5 miles from Anna Maria City Pier
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Anna Maria, Anna Maria Island
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Charming Cottage! Quiet North- End Oasis, Steps To Bay And Gulf. Heated Pool.1 / 22
    (47)Excellent
    0.5 miles from Anna Maria City Pier
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Anna Maria, Anna Maria Island
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Dream Vacation Destination! 8 bd Luxury Home with stunning Views! Pool and Spa!1 / 49
    (25)Very good
    0.0 miles from Anna Maria City Pier
    8 Bedrooms, 6 Bathrooms, Sleeps 18 Quick View
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    Anna Maria, Anna Maria Island
    Rental Home - 8 Bedrooms, 6 Bathrooms, Sleeps 18
    Visit AMI in Luxury! 5 bedroom home with pool and spa, AMAZING Rooftop Deck View1 / 45
    (18)Excellent
    0.6 miles from Anna Maria City Pier
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Anna Maria, Anna Maria Island
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    0.1 miles from Anna Maria City Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Anna Maria, Anna Maria Island
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Reduced Rates 25% OFF! 3 Minute Walk to Gulf Beaches!1 / 29
    (10)Excellent
    0.4 miles from Anna Maria City Pier
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Anna Maria, Anna Maria Island
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 14
    Luxury 3 bedroom beach bungalow with pool and spa! Canal front with dock!1 / 40
    (12)Excellent
    0.3 miles from Anna Maria City Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Anna Maria, Anna Maria Island
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Vacation in Luxury at this Beautiful home, great for families, close to beach!1 / 49
    (15)Very good
    0.2 miles from Anna Maria City Pier
    7 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    Anna Maria, Anna Maria Island
    Rental Home - 7 Bedrooms, 5 Bathrooms, Sleeps 16
    Beautiful, well-maintained home w/private pool - walk to beach, dining, & more!1 / 43
    (39)Excellent
    0.6 miles from Anna Maria City Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Anna Maria, Anna Maria Island
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Beach, Private Fishing dock, Heated Pool, Tropical Paradise1 / 29
    (47)Excellent
    0.4 miles from Anna Maria City Pier
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Anna Maria, Anna Maria Island
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    YOU Need a Getaway!! Waterfront and new city pier less than a block!1 / 38
    (43)Excellent
    0.6 miles from Anna Maria City Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 1 Quick View
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    Anna Maria, Anna Maria Island
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 1
    NEW HUGE Luxury Canalfront Home w/Canal &Bay Views, Pool/Spa, Bikes, Kayak, SUP!1 / 48
    (9)Excellent
    0.3 miles from Anna Maria City Pier
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Anna Maria, Anna Maria Island
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Spoonbill Hideaway-NOW FULLY OPEN!/Huge Pool/Spa/Across from Gulf Beach1 / 50
    (54)Excellent
    0.5 miles from Anna Maria City Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Anna Maria, Anna Maria Island
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Short stays and Dog friendly!1 / 19
    (13)Very good
    0.5 miles from Anna Maria City Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Anna Maria, Anna Maria Island
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Blue Heron Cottage - Anna Maria Island1 / 37
    (17)Excellent
    0.5 miles from Anna Maria City Pier
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Anna Maria, Anna Maria Island
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Seaside Maison, Family Friendly, 3 Blocks to Gulf, 2 Blocks to Rest. & Pine St.1 / 50
    (19)Excellent
    0.2 miles from Anna Maria City Pier
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Anna Maria, Anna Maria Island
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    30 Second Walk to the Beach ☼ Heated Pool1 / 31
    (5)Excellent
    0.7 miles from Anna Maria City Pier
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    Anna Maria, Anna Maria Island
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Reduced Rates 25% OFF! Just Steps from the Gulf Beaches with Private Pool/Spa!1 / 39
    (2)Excellent
    0.8 miles from Anna Maria City Pier
    4 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    Anna Maria, Anna Maria Island
    Rental Home - 4 Bedrooms, 6 Bathrooms, Sleeps 8
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