Holiday Rentals in Anna Maria Island, FL

Secluded in northwest Bradenton, this apartment offers a private retreat just a short drive from the shores of Anna Maria Island beaches and the natural beauty of Palma Sola Botanical Gardens.
This pet-friendly apartment boasts a generous 169 square meters of living space, accommodating up to 10 guests with a private pool and an expansive fenced backyard, ideal for families with dogs.

Just 160 metres from the bay in Bradenton Beach, this elevated two-level duplex offers a prime location for exploring the seaside.
This spacious, pet-friendly apartment sleeps up to 12 guests and boasts a tropical garden with a fire pit and sundeck, plus a private two-car garage and ample storage for recreational vehicles.

Boasting a private swimming pool and a spacious, fenced garden, this pet-friendly apartment in Palmetto offers an excellent user rating and is perfect for families or friends, located just over 5 kilometres from Tampa Bay and Bradenton Beach.
This dog-friendly accommodation features three bedrooms, two bathrooms, a dedicated movie room, and is conveniently situated near LECOM Park and Ellenton Ice and Sports Complex, ensuring a comfortable stay for up to eight guests with ample amenities including WiFi and air conditioning.

Ideally located in a quiet Bradenton residential neighbourhood, this dog-friendly apartment is conveniently situated between the beaches of Anna Maria Island and downtown's Riverwalk, offering easy access to the Riverwalk (2.3 kilometres) and Smuggler’s Cove Adventure Golf (2.2 kilometres).
This spacious 149 square meter apartment comfortably accommodates 8 guests with 3 bedrooms and 2 bathrooms, featuring a newly renovated interior, a fully equipped kitchen, central air conditioning, and an oversized, fully fenced backyard perfect for pets.

This pet-friendly apartment in Bradenton boasts a prime location, just 11 kilometres from the famous beaches of Anna Maria Island and a mere 5.5 kilometres from the IMG Academy.
Offering 118 square metres of living space for up to 8 guests, this dog-friendly apartment features a private fenced garden with outdoor dining and a fire pit, alongside essential beach gear for a comfortable stay.

This apartment in Holmes Beach is just a 4-minute walk from the white sands of Holmes Beach, offering a prime location near shops, dining, and water activities.
Enjoy a pet-friendly holiday with a heated community pool featuring a tropical waterfall and tiki hut, a private patio, and a fully equipped kitchen, conveniently located near boat rentals and sunset cruises.

This dog-friendly cottage in Holmes Beach is just 200 meters from the beach path, offering a serene botanical courtyard with a fountain and tropical landscaping.
Completely remodelled in 2025 with Old Florida charm and mid-century modern design, this pet-friendly accommodation features a spacious private porch, a new gym, and ground-level access.

Just 150 meters from the ocean beach, this Holmes Beach apartment offers prime access to dining and shops, with the Anna Maria Island Beach Cafe and its beachfront live music just a stroll away.
This 130 square meter, pet-friendly apartment boasts two bedrooms and two bathrooms, a fully equipped kitchen with granite countertops, and a private garden with a patio and grill, alongside ample parking and convenient access to the free island trolley.

Just steps from the beach path, this pet-friendly cottage in Holmes Beach offers direct access to Anna Maria Island's sugar-white sands and is within walking distance of local shops and restaurants.
This 75 square meter cottage boasts two bedrooms, two bathrooms, and a secluded patio with a stunning orchid wall, providing a private oasis alongside shared amenities including a gym and laundry facilities.

Directly on the powder-soft sands of the Gulf of Mexico, this Holmes Beach apartment in the Ilexhurst neighbourhood offers unparalleled beach access, just a minute's walk away and a short stroll to Publix, local shops, and dining.
This pet-friendly apartment, which allows small dogs, boasts 126 square meters of living space, a private patio with a gas grill, and high-speed Wi-Fi, comfortably accommodating up to four guests with the option to rent an adjoining unit for larger groups.

Perfectly situated in Bradenton, this pet-friendly house is just 2.7 kilometres from Palma Sola Causeway Park and 17.7 kilometres from The John and Mable Ringling Museum of Art.
This spacious 5-bedroom house offers a private swimming pool and garden, ideal for families and guests travelling with pets, alongside free WiFi and air conditioning for a comfortable stay.

Cortez Gardens Cottage 11 is located in Bradenton, just 6.4 kilometres from the Greens of Manatee Golf Club and 14.5 kilometres from the John and Mable Ringling Museum of Art.
This pet-friendly apartment offers a garden and is conveniently situated near the beach, making it ideal for a seaside getaway with your dog.

This canal-front house in Bradenton offers a private outdoor swimming pool and is located 17.7 kilometres from Sarasota International Convention Centre and 19.3 kilometres from the John and Mable Ringling Museum of Art, making it a perfect pet-friendly choice for your holiday.
With a floor area of 139 square metres, this air-conditioned accommodation boasts three bedrooms, two bathrooms, and a fully equipped kitchen, alongside free WiFi and on-site parking, ensuring a comfortable stay for up to 19 guests and their pets.

This pet-friendly apartment in Bradenton boasts a private heated saltwater pool and a dedicated pickleball court, offering fantastic recreation on its over 0.6-acre fenced yard.
Conveniently located 7 kilometres from Anna Maria Island beaches and 2.9 kilometres from IMG Academy, this family-friendly apartment with 4 bedrooms accommodates up to 10 guests and features a fully stocked kitchen.

This tropical house in Bradenton is located 2.6 kilometres from Palma Sola Causeway Park and 14.9 kilometres from Sarasota Bradenton International Airport.
This pet-friendly accommodation offers air conditioning, a heated swimming pool, and free Wi-Fi, making it ideal for families and travellers with pets.

This pet-friendly apartment is located on a private island in Bradenton, just a 2-minute drive from Manatee Beach on Anna Maria Island, offering a tranquil setting near essential amenities and natural beauty.
Spanning 138 square meters, this dog-friendly accommodation boasts two bedrooms, two bathrooms, and a guest capacity of five, featuring a fully equipped kitchen, air conditioning, a swimming pool, and a screened-in lanai for enjoying the seaside.

Just 1.1 miles from Cortez Beach and 6.7 kilometers from Anna Maria City Pier, this pet-friendly house offers a convenient base for exploring Cortez.
This air-conditioned house boasts a garden, spa, and a kitchen with a fridge, microwave, and dishwasher, ensuring a comfortable stay for you and your pets.

Just 500 metres from Cortez Beach, this pet-friendly house in Bradenton Beach offers excellent access to the seaside, being only 9.6 kilometres from Anna Maria City Pier.
This dog-friendly accommodation features a garden with barbecue facilities, complimentary WiFi, air conditioning, and a kitchen equipped with a fridge and microwave oven, ensuring a comfortable stay for families and their pets.

Boasting a private in-ground pool and outdoor seating, this pet-friendly apartment is conveniently situated just a 12-minute drive from Anna Maria Island and an 11-minute drive to Bradenton Beach, with a Publix grocery store and restaurants only 3 minutes away.
This spacious 143 square meter apartment accommodates up to 6 guests with 3 bedrooms and 2 bathrooms, featuring a fully stocked kitchen, comfortable living area with a large flat-panel TV, and a propane grill for outdoor cooking.

This canal-front house in Bradenton offers direct access to a boat dock and slip, conveniently located just 6.6 kilometres from The Ringling Museum and 6.3 kilometres from the Van Wezel Performing Arts Hall, making it an ideal pet-friendly base.
With 135 square meters of living space, this family-friendly property boasts 3 bedrooms, 2 bathrooms, a fully equipped kitchen, air conditioning, a swimming pool, a hot tub, and a garden, ensuring a comfortable stay with your pets.

This recently remodelled single-storey house is located near Anna Maria Island, offering a quick drive to its beaches, shopping, and restaurants, and is a truly pet-friendly destination for your holiday.
Boasting 241 square meters of living space, this dog-friendly home accommodates up to 8 guests with 4 bedrooms and 3 bathrooms, featuring a private heated pool, hot tub, resort-style outdoor kitchen, and a mini putting green for year-round enjoyment.

Just a short walk from the Gulf, this pet-friendly house in Holmes Beach offers a prime location for enjoying coastal life.
This elevated island retreat boasts 143 square meters of living space, accommodating up to 6 guests with 3 bedrooms, a heated community pool, a spacious deck with a grill, and extensive beach gear, making it ideal for families and their two pets.

This pet-friendly apartment in Bradenton is conveniently located within walking distance to GT Bray Park and just a 5-minute drive to IMG Academy, with area beaches like Bradenton Beach and Longboat Key a mere 10-minute drive away.
Offering a generous 158 square meters of living space for up to 9 guests, this dog-friendly apartment boasts a private outdoor oasis with a heated pool and spa, a wheelchair-accessible design, and an additional in-bathroom hot tub Jacuzzi for ultimate relaxation.

Boasting a prime West Bradenton location in the Palma Sola Bay area, this apartment is situated just 8 kilometres from the beautiful beaches of Anna Maria Island, Bradenton Beach, and Holmes Beach, offering a fantastic seaside escape.
This pet-friendly apartment provides ample space for up to 14 guests across its 4 bedrooms and 3 bathrooms, featuring a private heated swimming pool, hot tub, and extensive outdoor entertainment options including Giant Jenga and Cornhole.

This pet-friendly house in Holmes Beach offers excellent proximity to Anna Maria Island's shores, being just a 4-minute walk away and 3.4 kilometres from the historic Anna Maria City Pier.
With 167 square meters of floor area and featuring a swimming pool, fitness centre, and tennis court, this dog-friendly accommodation ensures a comfortable and active stay, complete with complimentary Wi-Fi.

Located in South Bradenton, this apartment is just a 10-15 minute drive from Downtown Bradenton and Sarasota, with Anna Maria Island also within easy reach and IMG Academy only 6 kilometres away.
This dog-friendly apartment offers 116 square meters of space for up to 8 guests, featuring 4 bedrooms and 4 bathrooms, alongside resort-style amenities including a swimming pool with a water slide and putt-putt, making it ideal for families and their pets.

Boasting a private, resort-style heated saltwater pool, this pet-friendly apartment in Bradenton's Palma Sola area is ideally situated on a cul-de-sac just 8 kilometres from the gulf beaches of Anna Maria Island, Holmes Beach, and Longboat Key, offering excellent value near local attractions and Palma Sola Bay beach.
This spacious 187 square meter apartment features 3 bedrooms and 2 bathrooms, accommodating up to 10 guests with a sleeper sofa, and includes a fully screened lanai overlooking a lush, fenced yard perfect for pets, along with provided beach gear for your convenience.

Just 500 meters from Palma Sola Bay and Anna Maria Island, this pet-friendly apartment in Bradenton offers easy access to beaches and water activities, making it ideal for dog-friendly holidays near the seaside.
This 177 square meter apartment boasts a private backyard with a lanai, gas grill, and heated pool (available for a nightly fee), alongside extensive beach gear and family amenities, accommodating up to 10 guests.

Cortez Gardens Cottage 15 is located in Bradenton, 14.5 kilometres from the Ringling Museum and 14.3 kilometres from the Sarasota International Convention Centre.
This pet-friendly, renovated 3-bedroom cottage offers a fully equipped kitchen, garden access, and is conveniently situated near the beach, making it ideal for families and those travelling with pets.

Conveniently located in Bradenton, this pet-friendly apartment is a short drive from theme parks and a water park, with Tampa Bay 34 kilometres away and Lido Beach 61 kilometres away.
This spacious 130 square meter apartment offers 4 bedrooms, 2 bathrooms, and accommodates up to 9 guests, featuring a garden with outdoor furniture, a deck, patio, and BBQ grill for an enjoyable stay with your pets.

This pet-friendly apartment in Bradenton is centrally located, just 12.9 kilometres from Anna Maria Island and 9.7 kilometres from Robinson Preserve, with a Publix supermarket only 4.8 kilometres away.
Enjoy a spacious 137 square metre, family-friendly apartment with 3 bedrooms, 2 bathrooms, and a guest capacity of 8, featuring a private heated pool, a screened lanai, and essential beach gear for your convenience.

Perfectly located in west Bradenton, this apartment offers easy access to Bradenton Beach, just 9.6 kilometres away, and IMG Academy, 3.2 kilometres distant.
This pet-friendly apartment boasts a privacy-fenced garden with a deck and a full kitchen, ideal for families and guests with electric vehicles, sleeping up to six people across two bedrooms.

Boasting a private resort-style backyard with a heated screened pool, hot tub, and fire pit, this pet-friendly apartment is situated in Bradenton's city centre, just 12-16 kilometres from the popular beaches of Anna Maria Island and Bradenton Beach.
This spacious 4-bedroom, 2-bathroom apartment comfortably accommodates up to 10 guests, offering a fully stocked kitchen, high-speed Wi-Fi, and is conveniently located within 11 kilometres of SRQ airport.

Palma Paradise, a pet-friendly apartment in Bradenton, is located in a quiet, family-friendly neighbourhood, just 10 minutes from Anna Maria Island and 10 minutes from IMG Academy.
This accommodation boasts a private, heated saltwater pool and spa, a fully equipped game room with air hockey and arcade games, and provides extensive beach equipment, making it ideal for families and their dogs.

Boasting an excellent location in Bradenton, this house is situated 2.7 kilometres from Palma Sola Causeway Park and a short drive from local beaches, with Sarasota Bradenton International Airport 13.9 kilometres away.
This pet-friendly house offers a private swimming pool and air conditioning, with a fully equipped kitchen and 3 bedrooms comfortably accommodating up to 10 guests for a memorable family holiday.

Conveniently located in Bradenton, this recently renovated house is just 10.0 kilometres from Sarasota Bradenton International Airport and 13.5 kilometres from the John and Mable Ringling Museum of Art.
This pet-friendly house boasts 181 square metres of living space, accommodating up to 15 guests with 3 bedrooms and 2 bathrooms, and offers a swimming pool, jacuzzi, spa, fitness centre, and tennis court for a complete holiday experience.