Holiday Rentals in Anna Maria Island, FL

Award-winning waterfront resort living on a private island offers a pet-friendly three-bedroom condo overlooking Anna Maria Sound, just a short distance from the charming shores of Anna Maria Island.
This spacious 153 square metre apartment boasts three bathrooms, accommodates up to seven guests, and features a fully equipped kitchen with a wine refrigerator, a large screened lanai perfect for watching Florida sunsets, and access to excellent resort amenities including a heated swimming pool and a deep-water marina.

This pet-friendly apartment in Palma Sola, Bradenton, is conveniently located just 7.1 kilometres from Anna Maria Island's beaches and 8.4 kilometres from IMG Academy, with Palma Sola Bay and Portosueno Park within walking distance for manatee spotting.
Boasting a generous 158 square metres of living space, this apartment offers four bedrooms, two bathrooms, and accommodates up to ten guests, featuring a private backyard with a swimming pool, a screened porch, a BBQ grill, and included beach gear.

This pet-friendly house in West Bradenton offers a delightful coastal escape, conveniently located just 2.6 kilometres from Palma Sola Causeway Park and a short drive from Sarasota Bradenton International Airport and The John And Mable Ringling Museum Of Art.
Boasting a generous 148 square metres of living space, this three-bedroom, two-bathroom holiday home comfortably accommodates up to 13 guests and features a private entrance, a balcony, air conditioning, a fully equipped kitchen, and on-site spa and swimming pool facilities.

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.

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.

Enjoy private beach access with a hammock and fire pit at this pet-friendly apartment, located just 3.2 kilometres from west coast beaches in Bradenton, near St. Armands Circle and Mote Marine Laboratory & Aquarium.
This spacious, newly decorated 5-bedroom, 2-bathroom apartment offers a fully stocked kitchen, complimentary beach essentials, and on-site parking, making it ideal for families or groups of up to 16 guests.

This pet-friendly apartment in West Bradenton is located in a quiet residential community, offering easy access to Anna Maria Island beaches, the DeSoto National Memorial, and Robinson Preserve, all within a few kilometres.
Boasting 259 square meters of space, this dog-friendly accommodation features a private heated pool, a large living area with an 82" SMART TV, and an updated kitchen, perfect for families of up to 10 guests with pets allowed.

Just a 6-minute stroll from the world-renowned white sands of Anna Maria Island, this Holmes Beach apartment offers a prime location near popular eateries like Ugly Grouper and The Feast Restaurant, making it a fantastic dog-friendly base for exploring the island.
Boasting a newly renovated kitchen with high-end appliances and a newly installed heated saltwater pool, this pet-friendly apartment comfortably accommodates up to six guests across 102 square meters, featuring two bedrooms and two bathrooms, with beach essentials and parking for two cars included.

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.

Just 300 meters from the powdery white sands of Anna Maria Island, this pet-friendly apartment in Holmes Beach offers a prime location near popular dining spots like The Ugly Grouper and The Feast.
This modern 2-bedroom apartment comfortably accommodates up to 6 guests and boasts a completely updated interior, a private heated pool with colour-changing lights, and a spacious tropical patio with outdoor dining and a Weber grill, making it ideal for seaside holidays with your dog.

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.

Boasting an excellent location in Bradenton, this apartment offers convenient access to popular beaches like Coquina Beach and Bean Point Beach, and is just a short drive from shopping at St. Armands Circle and the Mall at University Town Center.
This pet-friendly apartment features a private patio with a grill, a shared community pool with a waterslide, and is a fantastic choice for families and those travelling with their dogs, ensuring a comfortable and enjoyable stay near the seaside.

Located in a quiet and safe district of West Bradenton, this apartment offers a peaceful retreat, just a short drive from the coast.
This dog-friendly apartment features 3 bedrooms, 2 bathrooms, and accommodates up to 9 guests, boasting a swimming pool and garden for ultimate relaxation.

Just steps from the beach path, this pet-friendly cottage in Holmes Beach offers easy ground-level access and is conveniently located near Bradenton Beach and Bean Point Beach.
This dog-friendly cottage boasts a recently remodeled kitchen, a private garden patio, and access to a shared gym, comfortably accommodating two guests with its 64 square meters of floor area and one king master suite.

This apartment is located in Islands West Resort, just a 2-minute walk from Holmes Beach and close to shops, dining, and the island trolley.
This pet-friendly apartment accommodates up to 4 guests and offers a shared heated swimming pool and complimentary beach gear for a perfect seaside getaway.

Just a 5-minute walk from Anna Maria Island, this pet-friendly house in Holmes Beach offers excellent access to the seaside, located 26 kilometers from Sarasota International Convention Center and Sarasota Bradenton International Airport.
This spacious 130 square meter house features air conditioning, a swimming pool, a terrace, a garden, and a fully equipped kitchen, making it ideal for a dog-friendly holiday with free Wi-Fi and private parking.

This pet-friendly house in Bella Villa, Bradenton, is conveniently located 12.4 kilometres from Sarasota International Convention Centre and 12.6 kilometres from the John and Mable Ringling Museum of Art, with Sarasota Bradenton International Airport just 9 kilometres away.
Offering 110 square meters of space with 3 bedrooms and 2 bathrooms, this dog-friendly house boasts a swimming pool, a garden, an on-site restaurant, and excellent facilities for disabled guests, making it ideal for families travelling with pets.

Directly on Anna Maria Island, this pet-friendly house in Holmes Beach offers immediate beach access and is just 3.86 kilometres from the historic Anna Maria City Pier.
This dog-friendly accommodation boasts air conditioning, a swimming pool, a garden, and a spa, ensuring a comfortable and enjoyable stay for you and your pets.

Located in Bradenton, this cottage is just 2 kilometres from Anna Maria Island, offering a bike ride to the beach and Bridge Street, and less than 1 kilometre from the renowned Cortez Fishing Village and its seafood restaurants.
This dog-friendly cottage boasts a private outdoor oasis with a heated pool, hot tub, BBQ, fire pit, and entertainment options, accommodating up to 11 guests across three bedrooms and promising a phenomenal, pet-friendly stay.

Perfectly situated in Palma Sola, NW Bradenton, this apartment offers exceptional proximity to Anna Maria Island, the Manatee River, and Palma Sola Bay, all within a 1.6 kilometre walk or bike ride.
This pet-friendly apartment boasts a huge verandah and a lush fenced garden, ideal for families and offering 3 bedrooms accommodating up to 8 guests, with a fully outfitted kitchen and complimentary cruise bikes for exploring the nearby seaside attractions.

Boasting stunning sunset views over Anna Maria Sound, this pet-friendly apartment is located on a private island in Bradenton, just a 2-minute drive from Manatee Beach and local amenities.
This new, fully furnished 139 square meter condo offers an open layout for up to 5 guests, featuring resort-style amenities including a heated swimming pool, BBQ area, and complimentary bikes, making it ideal for a dog-friendly seaside escape.

Ideally situated in Holmes Beach, this pet-friendly holiday home is merely a 1-minute walk from the shores of Anna Maria Island, offering easy access to the seaside.
This 42 square meter house boasts a private swimming pool, spa facilities, and a garden, providing ample space for up to 7 guests and their pets to enjoy a comfortable stay with complimentary Wi-Fi and parking.

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.

Offering a private Old Florida oasis, this Bradenton apartment is conveniently located near IMG Academy and the Gulf beaches, a short drive away.
This spacious 223 square meter pet-friendly apartment boasts 3 bedrooms, 4 bathrooms, and accommodates up to 10 guests, featuring a private heated pool, an outdoor kitchen with a BBQ grill, and a unique mango tree platform with sunset views.

Just 500 meters from Holmes Beach's renowned white sand shores, this pet-friendly house offers a luxurious coastal retreat perfect for your family holiday.
This dog-friendly accommodation boasts a private heated pool and spa, along with three king bedrooms accommodating up to six guests, ensuring a comfortable and relaxing stay.

This pet-friendly apartment in west Bradenton is conveniently located just 800 meters from Anna Maria Island's beaches, dining, and activities, and only 24 kilometers from Sarasota Airport.
Offering 147 square meters of living space, this family-friendly apartment accommodates up to six guests with three bedrooms and two bathrooms, boasting a heated saltwater swimming pool, a garden, and a fully stocked kitchen with new stainless steel appliances.

Located in West Bradenton, this apartment offers convenient access, being just 10-16 kilometres from Anna Maria Island beaches, Downtown Bradenton, IMG Academy, and Robinson Preserve.
This **pet-friendly** apartment boasts 3 bedrooms, 2 bathrooms, and sleeps up to 8 guests, featuring a heated swimming pool, on-site mini-golf, a game room, and a fire pit for year-round enjoyment.

Just 50 metres from the white sandy beach, this newly updated 2-bedroom duplex apartment in Holmes Beach offers a prime location for your holiday.
This pet-friendly accommodation boasts a fully equipped kitchen, a garden with a BBQ, and is conveniently located near local attractions, making it an excellent choice for families and pets alike with its dog-friendly policy.

Runaway Bay, a peaceful district, places this 2-bedroom apartment just a short walk from Bradenton Beach and local shops, offering excellent walkability with a car being unnecessary.
This pet-friendly apartment boasts a newly remodelled interior with an open-concept layout, a private balcony with tropical views, and access to a heated outdoor pool and tennis courts, making it ideal for families and dog owners.

This pet-friendly house in Bradenton offers a private swimming pool and is located 5.9 kilometres from the beach, with free private parking and complimentary WiFi.
Boasting a fully remodelled interior, this 3-bedroom house accommodates up to 6 guests and features a kitchen with a dishwasher and oven, plus a washing machine for a comfortable stay.

Offering unobstructed water views of Anna Maria Sound and Tampa Bay, this luxury apartment in Bradenton is located within the area's only premier development, making it an excellent choice for a pet-friendly seaside escape.
This dog-friendly apartment boasts a gourmet kitchen, high-end furnishings, complimentary bikes, and abundant beach gear, perfect for a comfortable 7-guest stay with easy access to local attractions.

Ideally located in NW Bradenton, this pet-friendly house is under 5 kilometres from IMG Academy and Anna Maria Island, and 11 kilometres from the John and Mable Ringling Museum of Art and Sarasota International Convention Centre.
This comfortable 1-bedroom house, offering 1000 square meters of floor area, features air conditioning, free WiFi, a fully equipped kitchen with a dishwasher and oven, and a garden with an outdoor dining area, perfect for families and those travelling with pets.