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Duplex

Sunny Side Down

Sunny Side Down

Sunny Side Down Unit B by Anna Maria Vacations 2214 Avenue B, Bradenton Beach, Florida Welcome to Sunny Side Down! This colorful and cozy vacation rental is perfect for families or small groups in search of a tranquil beach escape. With two spacious bedrooms and two bathrooms, Sunny Side Down provides a harmonious balance of comfort and convenience, allowing you to unwind and enjoy your time together. Highlights • 3-minute walk to the Beach • 3-minute walk to Trolley Stop • Beach Chairs and Cart • Private Washer and Dryer • Dog friendly with approval and additional fee Spend your sun-soaked days lounging on the beach with the convenience of beach chairs and a cart provided to carry your essentials. The nearby Anna Maria Island Trolley stop enables you to access must-visit spots, including the Rod and Reel, AMI City Pier and Jail, and the vibrant shopping and dining areas at Bridge Street and Pine Avenue—all just a trolley ride away. Ascend to your private living quarters, featuring a bright and open layout that radiates warm coastal charm. The cozy seating area encourages relaxation, and the fully equipped kitchen, complete with island seating and a dining table for four, sets the perfect stage for quality family meals and shared laughter. Sunny Side Down boasts a primary bedroom with a king-sized bed and an ensuite bathroom designed for your convenience, featuring a shower-tub combination. The second bedroom is fitted with two twin beds, providing the ideal space for children or friends. A conveniently located hall bathroom with a shower-tub combo ensures all guests feel right at home. Room Details -Primary Bedroom, 2nd floor: King bed and ensuite bathroom with shower-tub -Second Bedroom, 2nd floor: Two Twin beds Don’t miss your chance to experience the serenity and joy of Sunny Side Down in beautiful Bradenton Beach! Reserve your stay now to create unforgettable memories in this delightful duplex oasis on Anna Maria Island! Traveling with friends and family? The next-door unit, Sunny Side Up, is also available for rent! Rent separately for an intimate getaway or combine both units for a larger group under the name “Sunny Side” on our All Rentals page. - Please note that nearby construction projects. This property allows pets - there will be an additional pet fee associated. Anna Maria Vacations Pet Policy: Dogs are allowed under certain conditions and ALL animals, including service animals, must be disclosed and approved prior to arrival. We cannot accept cats. *Please note that there will be an additional non-refundable pet fee charged upon approval by Anna Maria Vacations.* Weight limit of 50 lbs max total for 1 or 2 dogs combined. No dangerous breeds allowed. Please see our Anna Maria Vacations Rental Policies for full details. 2 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. This home is managed by Anna Maria Vacations, an Anna Maria Island property management company. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Anna Maria Vacations Rental Policies for full details. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

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Duplex

Sunny Side Up

Sunny Side Up

Sunny Side Up (Unit A) by Anna Maria Vacations 2214 Avenue B, Bradenton Beach, Florida Discover Sunny Side Up, a vibrant and inviting duplex rental in the heart of Bradenton Beach, perfect for families searching for a relaxing beach vacation. With two spacious bedrooms and two well-appointed bathrooms, this vacation home ensures a comfortable and enjoyable stay for all guests, and it's dog-friendly, too! Highlights • 3-minute walk to the Beach • 3-minute walk to Trolley Stop • Beach Chairs and Cart • Private Washer and Dryer • Dog friendly with approval and additional fee Spend sun-soaked days on the beautiful beaches, using beach chairs and a cart provided for effortless trips to the sand. The Anna Maria Island Trolley, just a short stroll away, offers easy access to local hotspots such as Rod and Reel, AMI City Pier and Jail, and the popular shopping and dining areas of Bridge Street and Pine Avenue. Ascend the stairs to your private living space, designed with an open layout that creates a warm and welcoming ambiance. The cozy seating area allows for relaxation while gathering with family and friends. The fully equipped kitchen includes island seating and a dining table for four, making it the perfect spot for enjoying meals together and creating lasting memories. Sunny Side Up features a spacious primary bedroom outfitted with a king-sized bed and an ensuite bathroom, complete with a shower-tub combination for your convenience. The second bedroom includes two twin beds, making it ideal for children or friends sharing the space. For additional comfort, a hall bathroom with a shower-tub combo is also available to accommodate all guests. Room Details -Primary Bedroom, 2nd floor: King bed and ensuite bathroom with shower-tub -Second Bedroom, 2nd floor: Two Twin beds Don’t let this perfect opportunity slip away! Experience the tranquility and joy of Sunny Side Up A in beautiful Bradenton Beach, where unforgettable memories await. Reserve your stay now and start planning your dream beach getaway on Anna Maria Island! - Please note that there are nearby construction projects. This property allows pets - there will be an additional pet fee associated. Anna Maria Vacations Pet Policy: Dogs are allowed under certain conditions and ALL animals, including service animals, must be disclosed and approved prior to arrival. We cannot accept cats. *Please note that there will be an additional non-refundable pet fee charged upon approval by Anna Maria Vacations.* Weight limit of 50 lbs max total for 1 or 2 dogs combined. No dangerous breeds allowed. Please see our Anna Maria Vacations Rental Policies for full details. 2 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. This home is managed by Anna Maria Vacations, an Anna Maria Island property management company. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Anna Maria Vacations Rental Policies for full details. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

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Duplex

Sunny Side

Sunny Side

Sunny Side by Anna Maria Vacations 2214 Avenue B, Bradenton Beach, Florida Welcome to Sunny Side: Your Ultimate Family Vacation Home on Anna Maria Island! Experience the ideal group getaway at Sunny Side, featuring both Sunny Side Up and Sunny Side Down, a spacious and inviting duplex located in the heart of beautiful Bradenton Beach on Anna Maria Island. Perfect for larger families or groups of friends, this super unit boasts a combined total of 4 bedrooms and 4 bathrooms, providing ample space for relaxation and connection. Highlights • 3-minute walk to the Beach • 3-minute walk to Trolley Stop • Beach Chairs and Cart • Two Private Washer and Dryer • Dog friendly with approval and additional fee • Two Separate Living Spaces • Perfect for Groups Spend your sunny days soaking up the sun on the beach, shopping along Pine Avenue and Bridge Street, exploring local history at the AMI City Pier and Jail, and indulging in acclaimed restaurants. After a day of adventure, retreat to your spacious, separate accommodations. Each unit boasts an open layout with cozy seating, fully equipped kitchens, and inviting dining spaces, creating the perfect hub for shared meals and cherished moments with family and friends. Sunny Side Up and Sunny Side Down offer mirrored bedroom layouts, each featuring a king suite with an ensuite bathroom that includes a shower-tub combo alongside a twin bedroom and a hall bathroom with a shower-tub combo. This thoughtful design ensures that every guest feels comfortable and at home during their stay. Room Details Sunny Side Up: -Primary Bedroom, 2nd floor: King bed and ensuite bathroom with shower-tub -Second Bedroom, 2nd floor: Two Twin beds -Bonus: Sleeper Sofa Sunny Side Down: -Primary Bedroom, 2nd floor: King bed and ensuite bathroom with shower-tub -Second Bedroom, 2nd floor: Two Twin beds -Bonus: Sleeper Sofa Don't miss the chance to experience the joy and tranquility of Sunny Side, where you can create unforgettable memories with those who matter most. Reserve your stay now for the ultimate beach getaway on Anna Maria Island! - Please note that there are nearby construction projects. This property allows pets - there will be an additional pet fee associated. Anna Maria Vacations Pet Policy: Dogs are allowed under certain conditions and ALL animals, including service animals, must be disclosed and approved prior to arrival. We cannot accept cats. *Please note that there will be an additional non-refundable pet fee charged upon approval by Anna Maria Vacations.* Weight limit of 50 lbs max total for 1 or 2 dogs combined. No dangerous breeds allowed. Please see our Anna Maria Vacations Rental Policies for full details. 4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. This home is managed by Anna Maria Vacations, an Anna Maria Island property management company. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Anna Maria Vacations Rental Policies for full details. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

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Condo

Tropical Terrace 3

Tropical Terrace 3

Tropical Terrace 3 by Anna Maria Vacations 3100 Gulf Dr #3 Holmes Beach, FL 34217 Just a 2-minute stroll from the beautiful beaches of Anna Maria Island, Tropical Terrace 3 is the perfect retreat for a memorable vacation. This newly renovated two-bedroom, two-bathroom rental features coastal décor and is close to fantastic dining, shopping, community parks, and entertainment centers including The Island Players and The Center of Anna Maria Island. Embrace relaxation and create lasting memories in this amazing location! Highlights • 2-minute walk to the beach • 2-minute walk to Trolley stop • Shared heated pool • Nearby recreational rentals • Balconies • Private washer and dryer • Beach chairs, wagon, cooler, and toys • Shared outdoor seating area • BBQ Grill At Terrace 3, guests are invited to take full advantage of fantastic community amenities! Dip into the sparkling swimming pool, relax on comfortable lounge chairs, and gather around the outdoor table. Plus, enjoy the convenience of a private enclosed garage with plenty of pool and beach amenities, including a BBQ grill and cooler, perfect for beach days and delicious cookouts! Step into a welcoming living room with a 55-inch TV designed for relaxation and comfort, seamlessly flowing into a chic dining area. The fully equipped kitchen has all the essentials for cooking up your favorite meals, complete with island seating and a Keurig to savor your morning coffee and tea. Tropical Terrace 3 features two comfortable queen bedrooms, each beautifully decorated with beach-themed touches and Cariloha pillows, complete with 42-inch tvs with Roku sticks and balcony access. The downstairs bathroom includes a walk-in shower, while the upstairs bathroom has a shower-tub combination. Additionally, the living room provides a convenient sleeper sofa for accommodating extra guests. Room Details -Primary Bedroom: Queen bed and balcony access -Second Bedroom: Queen bed and balcony access -Living Room: Sleeper Sofa Don’t miss the chance to experience the beauty of Anna Maria Island from the comfort of Tropical Terrace 3! Input your desired dates now and take the first step toward planning your perfect vacation with Anna Maria Vacations. - This home is managed by Anna Maria Vacations, an Anna Maria Island property management company. This property does not allow pets of any kind. 2 cars maximum are able to park at this homes enclosed garage. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Anna Maria Vacations Rental Policies for full details. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

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House

Somewhere in the Sun

Somewhere in the Sun

Highlights • Less than a 5-minute walk to the beach • Rooftop deck • Pool with in-ground spa • Outdoor living space • Brand new construction Somewhere in the Sun by Anna Maria Vacations 2410 Avenue B Bradenton Beach, Florida Welcome to Somewhere in the Sun, a stunning seven-bedroom and six-and-a-half-bathroom brand-new home! Every inch of this getaway has been thoughtfully designed with comfort and luxury in mind, and we can't wait for you to experience it. From the awe-inspiring rooftop deck boasting stunning views of the beach and bay to the lush tropical backyard, complete with a private pool and spa, you'll have everything you need for a perfect vacation. The open living space radiates vacation vibes with a coastal seating area with two sofas and side chairs. To create an even calmer atmosphere, open the sliding doors leading to the main floor balcony, where you might get a glimpse of the Gulf. The kitchen is fully equipped with stainless steel appliances, essential cookware, and a large kitchen island with barstools, perfect for sipping wine while dinner is cooking. Additionally, there is a formal dining room table. The primary bedroom is designed for ultimate relaxation and has a deluxe mattress and a balcony that offers stunning island views. The primary ensuite bathroom has a double vanity and a spacious walk-in shower. There are five king bedrooms, three featuring ensuite bathrooms with walk-in showers and one that shares a jack-n-jill bathroom with a walk-in shower with the bunk bedroom. Additionally, there is a loft area that has a comfortable sofa (that can convert into a sleeper sofa!) and a large TV for entertainment. -Primary Bedroom, 3rd floor: King bed and ensuite bathroom with walk-in shower -Second Bedroom, 3rd floor: King bed and ensuite bathroom with walk-in shower -Third Bedroom, 3rd floor: King bed and ensuite bathroom with walk-in shower -Fourth Bedroom, 2nd floor: King bed and ensuite bathroom with walk-in shower -Fifth Bedroom, 3rd floor: King bed -Sixth Bedroom, 2nd floor: King bed and Jack and Jill bathroom with walk-in shower -Seventh Bedroom, 2nd floor: Twin over twin bunk and Jack and Jill bathroom with walk-in shower -Common Area, 3rd floor: Queen Sleeper Sofa We are thrilled to offer our guests the ultimate outdoor oasis at Somewhere in the Sun. When you're not on the rooftop deck or at the beach, relax in style on our high-end outdoor sectional, dip in the sparkling pool, and savor delicious meals cooked on the BBQ grill at the outdoor dining table. Discover the beauty of Anna Maria by hopping on the free trolley, walking, or renting a golf cart. Hang out with the locals on the historic City Pier, dine under the stars at beachfront restaurants, visit the shops along Pine Ave., and create endless memories at the dreamy beaches. - This property has an active Ring doorbell at the main entrance. This property does not allow pets. 4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. This home is managed by Anna Maria Vacations, an Anna Maria Island property management company. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Anna Maria Vacations Rental Policies for full details. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

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Condo

Beachy Butterfly

Beachy Butterfly

Beachy Butterfly by Anna Maria Vacations 600 Manatee Ave #219, Holmes Beach, FL 34217 Welcome to Beachy Butterfly, a recently refreshed 2-bedroom, 2-bathroom condo perfect for families looking for a relaxing beach getaway. Nestled in the heart of Holmes Beach, this charming property offers a serene escape just a 10-minute walk from the beautiful sandy shores, with nearby restaurants and a grocery store for added convenience. Highlights • 10-minute walk to the Beach • Community Pool • Community Tennis/Pickleball Court • In-unit Washer and Dryer • Near Shopping and Dining • 3-minute walk to Anna Maria Island Trolley stop • 30-night minimum stay Enjoy the beautiful Florida sunshine and scenic views from the outdoor shared pool and tennis and pickleball court, perfect for some fun in the sun. Your private Florida room overlooks the spacious landscape and pool area, providing a relaxing space to unwind after a day at the beach. This inviting condo features a bright living room drenched in natural lighting that flows into a fully equipped kitchen, complete with a refrigerator, stove, dishwasher, Keurig coffee maker, toaster, and microwave – perfect for preparing meals or enjoying your morning coffee. The dining area comfortably accommodates six family members. Beachy Butterfly boasts a coastal-inspired primary bedroom equipped with a king-sized bed, an ensuite bathroom featuring a walk-in shower, and a spacious walk-in closet. The second bedroom is perfect for the little ones or extra guests, featuring two twin beds, an ensuite bathroom with a shower-tub combo, and a walk-in closet. Room Details -Primary Bedroom: King bed and ensuite bathroom with walk-in shower -Second Bedroom: Two Twin beds and ensuite bathroom with shower-tub Don’t miss out on your chance to create unforgettable vacation memories at Beachy Butterfly! Book your stay today through Anna Maria Vacations and enjoy all the comforts of home in an ideal beach town! - This home is managed by Anna Maria Vacations, an Anna Maria Island property management company. This property does not allow pets of any kind. 1 reserved parking spot is provided. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Anna Maria Vacations Rental Policies for full details. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

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Condo

Island Tropical Villa

Island Tropical Villa

Highlights • 5-minute walk to the beach • Community pool access • BBQ grill • Washer and dryer • Multiple outdoor decks with seating • Dog Friendly • Screened-in lanai • Beach chairs • Outdoor shower Island Tropical Villa by Anna Maria Vacations 237 64th St, Holmes Beach, FL 34217 Escape to Island Tropical Villa, your perfect vacation home situated on the beautiful Anna Maria Island. This newly updated three-bedroom, two-bath retreat offers everything you need for a relaxing getaway, including North Beach Village community pool access. Located just minutes from Florida's best beaches, you can easily enjoy sun, sand, and surf. The main living floor features a cozy seating area with a large TV, a fully equipped kitchen with quality appliances, a 10-cup traditional coffee maker, a 4-slice toaster, and more. Gather around the indoor dining table that seats six for a family meal or take advantage of the beautiful Florida evenings by dining al fresco on the screened-in lanai, where another dining table awaits. The primary suite offers a plush king bed, a closet, and an ensuite bathroom with a walk-in shower. Guest rooms on the upper floor have delightful decor all done by a professional interior designer, emphasizing a relaxing and inviting atmosphere. There is a shared bathroom with a walk-in shower. Room Details -Primary Bedroom, 2nd floor: King bed and ensuite bathroom with walk-in shower -Second Bedroom, 3rd floor: Queen bed -Third Bedroom, 3rd floor: Double bed Enjoy the provided beach chairs and rinse off after a beach day with the outdoor shower featuring hot and cold water. Two decks wrap around the house, offering ample space to unwind. The community pool area with lounge chairs and bathrooms for guest use is just a minute away. Pack your beach towel and head to Island Tropical Villa for an unforgettable vacation! - This home is managed by Anna Maria Vacations, an Anna Maria Island property management company. This property allows dogs with host approval prior to arrival. Please note there will be an additional pet fee associated, see our Anna Maria Vacations Rental Policies for full details. 4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

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Condo

Dolphin Baycation at Runaway Bay

Dolphin Baycation at Runaway Bay

*pool and tennis courts are currently unavailable* Dolphin Baycation by Anna Maria Vacations 1801 Gulf Dr. N #290, Bradenton Beach, FL 34217 Welcome to Dolphin Baycation, your perfect Anna Maria Island condo for families and small groups! This charming 2-bedroom, 2-bathroom condo is ideally situated just a leisurely 4-minute walk from the stunning beaches of Bradenton Beach. Experience breathtaking bay views and enjoy the convenience of being close to the Anna Maria Island trolley stop, which makes it easy to explore beloved island restaurants, shops, and landmarks. Highlights • 4-minute walk to the beach • Community Heated Pool • Community Tennis/Pickleball Court • Community Bocce Ball and Shuffleboard Court • Private Balcony with Bay Views • In-unit Washer and Dryer • Beach Chairs At Runaway Bay Condominiums, enjoy excellent outdoor amenities that make the most of island life. Relax at the large heated pool, play tennis or shuffleboard, or unwind in the scenic picnic area with BBQ grills. With a fitness facility, kayak launch, and fishing pier on-site, you’ll find the perfect blend of leisure and recreation. Step inside Dolphin Baycation to discover a welcoming living room with comfortable seating and a soothing coastal ambiance, perfect for unwinding after a day of sun and sand. The open-concept kitchen is fully equipped with modern appliances, ideal for preparing home-cooked meals, and it flows into a cozy dining area. Enjoy your morning coffee or evening sunsets on your private balcony overlooking the bay. Retreat to the primary bedroom, a luxurious space featuring a king bed, bay views, a spacious walk-in closet, and an ensuite bathroom with a walk-in shower. The second bedroom is designed for versatility, offering a queen bed and a twin bed, perfect for children or additional guests. A conveniently located hall bathroom with a shower-tub combo ensures that everyone has ample space. Room Details -Primary Bedroom: King bed and ensuite bathroom with walk-in shower -Second Bedroom: Queen and Twin bed Ready to experience the ultimate beach getaway? Book your stay at Dolphin Baycation today and create unforgettable memories with family and friends in this beautiful condo! - This home is managed by Anna Maria Vacations, an Anna Maria Island property management company. This property does not allow pets of any kind. One reserved parking spot is provided. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Anna Maria Vacations Rental Policies for full details. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

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