The widest selection of unusual accommodations in Anna Maria Island, FL

About: This smoke-free cabin is situated in Holmes Beach, within a 10-minute walk of Bradenton Beach and Island Gallery West. With excellent user, location, and cleanliness ratings, this cabin offers a comfortable and convenient stay.

The cabin features a well-equipped kitchen, a private patio, barbecue grills, and a DVD player. It has a 2-bedroom layout to accommodate up to four guests and it includes a swimming pool, a garden, a restaurant, air conditioning, internet, a terrace or balcony, and parking.

About: This Holmes Beach vacation home is centrally located in the city center, within walking distance of supermarkets and restaurants and steps to the Gulf of Mexico. It has been rated as excellent by previous guests.

This 1800 square feet property has 3 bedrooms and 2 bathrooms, and can accommodate up to 6 guests. It features a large kitchen with granite countertops, a huge laundry room, and TVs in all bedrooms. Guests can also enjoy a gas BBQ on the back patio, an outside shower with hot/cold water, and a tennis court.

About: This bungalow is a quiet and intimate one-bedroom, one-bathroom beach house located directly on Bradenton Beach. It is within walking distance of Aluna Wellness Center & Spa and Fish Hole Adventure Golf (less than 0.5 miles) and close to Coquina Baywalk and Robinson Preserve (within 1 mile). It has an excellent user rating.

It is perfect for a romantic getaway or a small family vacation, accommodating up to 4 guests. The bungalow features a full kitchen, queen sleeper sofa, and jacuzzi jet bathtub. It also offers access to a shared courtyard with a barbecue area and fire pit.

About: This bungalow is located in Holmes Beach on Anna Maria Island, just a block from the Gulf of Mexico beaches. It has an excellent user rating and can accommodate up to 6 guests in its 3 bedrooms and 2 bathrooms.

The bungalow has a private deck, a well-equipped kitchen, air conditioning, a swimming pool, a garden, a spa, and parking. It is also pet-friendly and has wireless internet and cable TV.

About: This boat is located in Cortez, Florida, one block from the Cortez Bridge and the beach, and just steps away from the beach, bay, piers, park, shopping and restaurants. It has excellent user ratings.

The boat has a floor area of 3000 square feet, 3 bedrooms, 3 bathrooms, and a guest capacity of 10. It features a modern and elegant interior design with plenty of natural light and stunning views of the ocean and sunsets. Amenities and features include free Wi-Fi, two kitchens, two dining rooms, two living rooms, flat-screen TVs in every room, a baby crib, a game room with a ping pong table, a six-burner BBQ grille, a custom-designed pool with waterfalls, jets, bubblers, colored lights, extra-large sun shelves, and state-of-the-art equipment, a full garage with six bicycles, kayaks, beach chairs, boogie boards, beach toys and floats, boat and fishing supplies, more games, ice chests, frisbees, footballs, and more vacation supplies.

About: This bungalow is located on 68th Street in Holmes Beach, just one block from the beach and within walking distance of restaurants, pubs, and shops. It has an excellent user rating, and it's pet-friendly, allowing up to 2 dogs with a non-refundable fee.

The bungalow has 4 bedrooms, 3 full bathrooms, and can accommodate up to 8 guests. It features a large heated pool, a massive outdoor covered cabana with a big screen TV and patio, and a newly landscaped patio with parking for 4 cars, a barbecue grill, and outdoor seating. It also has modern amenities such as 5 flat-screen TVs, stainless steel appliances, granite countertops, free phone/cable/wireless internet, and a fully equipped kitchen.

About: Casa Del Mar is a Key West-style home located on the north end of Holmes Beach, within walking distance of white sandy beaches, shopping, and restaurants. The home has received excellent user ratings and offers a comfortable and welcoming atmosphere.

The home has four bedrooms, three bathrooms, and a floor area of 1850 square feet, making it suitable for up to eight guests. Amenities include a fully-equipped kitchen, air conditioning, a heated pool, a terrace/balcony, a spa, and parking. The home also offers supplemental services such as pre-stock grocery shopping and babysitting.

About: CabAnna Maria is a 4-bedroom vacation home located in Anna Maria, near the beach, Island Players, and Anna Maria Island Museum and Historical Park. It has excellent user ratings.

The cabin has a floor area of 2120 square feet and can accommodate up to 8 guests. It features a private heated pool and spa, stand-up paddleboards, kayaks, life vests, bicycles, helmets, beach chairs, umbrellas, and fishing poles. It also includes a custom-built bunk room and professional linen service.

About: This Holmes Beach bungalow is located in a peaceful neighborhood with mostly second homes, providing a quiet and relaxing ambiance. It's just a short walk from the beach and close to family-friendly activities, nightlife, public transport, and the airport.

The bungalow has received excellent ratings for its location, cleanliness, and amenities. It has one bedroom, one bathroom, and can accommodate up to three guests. The kitchen is equipped with a fridge, freezer, and microwave oven. The bungalow also has air conditioning, a garden, and parking. It's a great option for travelers looking for a comfortable and convenient place to stay in Holmes Beach.

About: This Holmes Beach bungalow is just 469 feet from the Gulf of Mexico, in the heart of Holmes Beach, within easy reach of shops, restaurants, and other amenities. It has excellent user, location, and cleanliness ratings.

The one-bedroom, one-bathroom bungalow accommodates up to three guests and features a well-equipped kitchen, air conditioning, a garden, parking, and a private deck or patio.

About: Pine Avenue HideAway is a secluded beach bungalow on historic Pine Avenue in Anna Maria's North End, steps from the beach, restaurants, boutiques, and the Anna Maria City Pier. It has excellent user ratings.

The bungalow has a modern and stylish interior with two bedrooms, two bathrooms, wood floors, stainless appliances, granite countertops, and a cozy coastal feel. It has a floor area of 1050 square feet and can accommodate up to 4 guests. Amenities include an oversized private deck with a hot tub, propane grill, and outdoor dining for four, as well as three flat-screen TVs with cable access, Wi-Fi, and a full-size washer and dryer.

About: This house is situated in Bayshore Gardens, within a 3-mile radius of attractions like State College of Florida and IMG Soccer Academy. It has an excellent user rating.

The house has 3 bedrooms, 2 bathrooms, a sofa bed, and a fully equipped kitchen. It can accommodate up to 8 guests. It also has a private outdoor pool, a garden with barbecue grills, and a terrace/balcony. The house is pet-friendly, family-friendly, and has free WiFi.

About: The H2O Bungalow is situated in Anna Maria, a short walk from Gulf Drive's shops and restaurants, and just two blocks from the white-sand Gulf beach. It has received excellent user ratings, making it a highly sought-after vacation rental.

The bungalow features a spacious 1840 square feet layout with three bedrooms and three bathrooms, accommodating up to eight guests. It boasts a gourmet kitchen, a private lazy river pool with a hot tub, and a massive outdoor space with a charcoal grill, loungers, and tables. Guests can also enjoy amenities such as air conditioning, internet, a dishwasher, a microwave oven, a fridge, beach chairs, umbrellas, and a cart for easy beach access.

About: This bungalow is located in Anna Maria, a quiet and family-friendly area known for its beautiful beaches and charming atmosphere.

The bungalow has a floor area of 1050 square feet and can accommodate up to 4 guests in 2 bedrooms. It features a fully equipped kitchen, air conditioning, a swimming pool, a jacuzzi, a garden, and parking.

About: This bungalow is a luxurious and welcoming retreat in Holmes Beach, Anna Maria Island. It is a short distance from popular destinations such as Bean Point and historic Bridge Street, and just a 2-minute walk from the beach.

The 4-bedroom, 3-bathroom bungalow has a unique beach decor, with luxurious touches such as 5 flat-screen TVs, stainless steel appliances, beautiful wood tile floors, and granite countertops. It accommodates up to 8 guests and features a 32-foot heated pool with a waterfall, sun step for children, and a relaxing spa. Guests will also appreciate the convenience of having a fully stocked garage with kayaks, bikes, a wagon, toddler tricycle, beach chairs, umbrellas, and toys.

About: Bayfront Paradise is a luxurious 5-bedroom, 7-bathroom vacation home situated in Bradenton Beach, Florida, just a short walk from the beach. It has received excellent user ratings, making it a top choice for travelers seeking a comfortable and enjoyable stay.

The home boasts a spacious 2,640 square feet of living space, comfortably accommodating up to 14 guests. It features two fully equipped kitchens, a private heated pool with a spa, multiple porches for outdoor relaxation, and a private boat dock for convenient access to the bay. Guests can also enjoy stunning bay views from multiple areas of the home, including a rooftop deck with panoramic views of the bay and Gulf sunsets.

About: The Pirate's Den is a 1-bedroom, 1-bathroom bungalow located steps from the Gulf of Mexico beach access in Holmes Beach. The bungalow has an excellent user rating, location rating, and cleanliness rating.

The Pirate's Den has a full kitchen and living area, a private backyard oasis with a heated saltwater pool and spa, and a shared backyard space. The bungalow also has free Wi-Fi, air conditioning, and a starter set of supplies.

About: The Captain's Quarters bungalow is located in Holmes Beach, just steps from the Gulf of Mexico beach and one block from the free trolley stop. With excellent user, location, and cleanliness ratings, this one-bedroom, one-bathroom bungalow can accommodate up to four guests.

The bungalow features a heated saltwater pool and spa, a gas grill, a spacious layout, and a starter set of supplies. Guests can also enjoy the coastal-inspired interior design, access to shops and restaurants, and the free trolley service nearby.

About: The Pirate's Den bungalow is a duplex-style bungalow located in Ilexhurst, Holmes Beach, a block away from the free trolley stop and within easy reach of shops and restaurants. It has an excellent user rating.

This one-bedroom, one-bathroom bungalow has a spacious layout with a trundle and full kitchen and living area. It can accommodate up to four guests and has a floor area of 680 square feet. The bungalow also features a shared backyard space with a heated saltwater pool, spa, and gas grill.

About: The Pirate's Den bungalow is a beachfront property located in the Ilexhurst neighborhood of Holmes Beach, just steps away from Gulf of Mexico beach access and one block from the free trolley stop. It has received excellent user ratings and offers a unique vacation experience.

The bungalow has a floor area of 680 square feet and can accommodate up to 4 guests. It features 1 bedroom, 1 bathroom, a fully equipped kitchen, a living area with a sleeper sofa, and a private patio. Guests can enjoy amenities such as a heated saltwater pool and spa, a gas grill, and free Wi-Fi.

About: This lighthouse vacation rental in Holmes Beach is a unique accommodation option for travelers seeking a charming and memorable stay. Just a 6-minute walk from the beautiful Gulf beach, this lighthouse offers excellent user ratings.

With 3 bedrooms, 3 bathrooms, and an open plan living area, the lighthouse has a floor area of 1750 square feet and can accommodate up to 6 guests. The private pool, retro decor, and proximity to attractions like Bean Point Beach and Anna Maria Beach make this lighthouse an excellent choice for families and groups seeking a comfortable and entertaining vacation experience.

About: Salty Dog is a two-bedroom, one-bathroom bungalow located in Holmes Beach, Florida, a short two-minute walk from the Gulf of Mexico. It has an excellent user rating.

This 840-square-foot bungalow can accommodate up to six guests and features a fully equipped kitchen, a comfortable living room with a queen sleeper sofa, a primary bedroom with a king-sized bed, a second bedroom with two twin beds, and a private backyard with a saltwater pool, ample lounge chairs, a BBQ grill, and an outdoor seating area. Amenities include air conditioning, internet, a washer and dryer, and parking for up to two cars.

About: Situated on the tranquil Anna Maria Island, Mango Mews offers a luxurious vacation home experience in Holmes Beach. This spacious 4-bedroom, 3-bathroom property is just a short walk from the pristine emerald coastline, providing guests with easy access to the island's award-winning beaches.

The home features a private pool and heated spa, a gaming area, and a spacious balcony with panoramic views. Inside, the modern interior boasts a fully equipped kitchen, comfortable living areas, and a dining area that steps out to the outdoor lounging area. The home accommodates up to 8 guests, making it perfect for families or groups seeking a memorable beach getaway.

About: This spacious 3-bedroom vacation home is located in Bradenton, a 10-minute drive from Bradenton Beach, within easy reach of Holmes Beach and numerous attractions. It has an excellent user rating.

The cabin features a spacious living area, a fully equipped kitchen, an outdoor pergola, a master bedroom with a queen-size bed and a private bathroom, guest bedrooms featuring a queen-size bed and two twin-size beds, a bright and calming Florida room, and a garage with a second fridge, washer, and dryer. It has a floor area of 1500 square feet and a guest capacity of 6.

About: Tina's Piece of Paradise is a vacation rental located in Holmes Beach, within walking distance to the pristine Gulf of Mexico beaches. This four-bedroom, three-bathroom accommodation comfortably accommodates up to eight guests.

The rental features a private heated pool, a patio area, a game room, and a fully equipped kitchen. Guests can also enjoy the coastal décor, premium hotel-quality linens, comfortable beds, and flat-screen televisions in each bedroom.

About: This Holmes Beach bungalow is a perfect choice for families seeking a comfortable and convenient vacation rental. With a very good user rating, this 4-bedroom bungalow sleeps up to 8 guests and offers 1800 square feet of living space.

The bungalow features a fully equipped kitchen, air conditioning, a private swimming pool, a Jacuzzi, a garden, a fitness center, and parking. Guests can also enjoy free Wi-Fi and access to a variety of amenities and activities.

About: Benny's Bungalow is a luxury waterfront vacation home located on Bradenton Beach, a quick 5-minute walk from the pristine shores and less than a mile from Bridge Street Pier. The bungalow has received excellent user ratings and can accommodate up to 16 guests in its seven en suite bedrooms and seven and a half bathrooms, with a total floor area of 3120 square feet.

The bungalow features a private heated pool and jetted spa for relaxation, a rooftop deck with breathtaking Gulf views, a gourmet kitchen with top-of-the-line appliances, and an open floor plan on the second floor with inviting living and dining areas. Guests can also enjoy complimentary AMI Trolley service to explore the island's North End, as well as exclusive amenities such as a private dock, kayaks, and paddleboards.

About: This houseboat is located in Cortez, a 10-minute walk from Canal Anna Maria Sound and a 9-minute walk from Florida Maritime Museum at Cortez. It has 2 bedrooms, 1 bathroom, and a guest capacity of 6.

The houseboat has a private dock, a private deck with outdoor furniture, air conditioning, a desk, and a water dispenser. Towels, toilet paper, and soap are provided. On-site activities and amenities include a boat, water sports equipment, and a heated pool.

About: This bungalow in Bradenton Beach is a perfect choice for families seeking a coastal retreat. Just steps from the beach and a short walk from Bridge Street Pier, it offers a prime location with excellent user and location ratings.

The bungalow features two bedrooms, two bathrooms, and a spacious layout that can accommodate up to six guests. It is fully equipped with modern amenities, including a well-stocked kitchen, comfortable beds, free Wi-Fi, and air conditioning. Guests can also enjoy a private patio or balcony, a garden, and on-site parking.

About: Island listing from $417 for up to 6 guests with an excellent rating of 100% based on 1 reviews. You will stay in Holmes Beach.

Services and facilities: a barbecue, a washing machine and a dish washer. Enjoy free parking with this accommodation in Holmes Beach!

About: Centrally located in Holmes Beach on Anna Maria Island, just 2.5 blocks from the beach, this 2 bedroom, 2 bathroom home is the perfect place to stay for your next vacation. With excellent user ratings, this home offers a unique location near numerous restaurants and bars, and close to Anna Maria City Pier, Aluna Wellness Center & Spa, Coquina Baywalk, Robinson Preserve, AMI Paddleboard Adventures, and Fish Hole Adventure Golf.

The well-appointed 1/2 duplex home has a fully equipped kitchen and TVs in both living rooms. It also has a keyless entry system, full-size washer and dryer, WiFi, cable, and parking for two cars. The home has a floor area of 1500 square feet and can accommodate up to 6 guests. Guests can enjoy the heated pool, outdoor shower, gas BBQ grill, beach chairs, and free island trolley service.

About: Parrot Landing is located in the Sunny Shores neighborhood of Bradenton, just a short distance from Cortez Beach and the beaches of Anna Maria Island. It has an excellent user rating.

Parrot Landing has 3 bedrooms, 2 bathrooms, and a floor area of 1440 square feet. It can accommodate up to 10 guests. The island has a large living room, a well-equipped kitchen, and an outdoor cooking area. It also has a heated above-ground pool, a garden, and a spa. Guests can enjoy unique tropical plantings and Adirondack chairs on the deck for gathering and relaxation. They also have access to the free Anna Maria Island Trolley for exploring the island.

About: Mango Beach House is a beachfront paradise located on Bean Point in Anna Maria, offering direct access to the Gulf of Mexico. It is within walking distance to the Sand Bar Restaurant and a short drive from Historic Pine Ave. It has an excellent user rating.

The open floor plan with colorful furnishings and flat screen TVs in all bedrooms and living area creates a comfortable and inviting space for up to 8 guests. The fully air-conditioned home features a kitchen with modern appliances, a large patio with gas BBQ grill, two bathrooms with walk-in showers, a stacked washer and dryer, free WiFi, and CCTV cameras for security and privacy. Guests can enjoy beach activities, free trolley service to explore Anna Maria Island, and more.

About: Anna Maria Island offers a unique and serene waterfront vacation experience. Just steps from Bean Point Beach and a short walk from the charming Pine Avenue, this vacation home provides easy access to the island's attractions. With a very good user rating, the island guarantees a comfortable stay.

The 1350 square foot island has two comfortable bedrooms with Samsung Smart TVs, two bathrooms, and a guest capacity of six. The fully equipped kitchen, screened-in lanai, and private dock with saltwater pool and tanning shelf make it an ideal choice for families and groups seeking a relaxing and enjoyable vacation.

About: Southern Breeze #4 is a 2-bedroom, 1-bathroom vacation rental at the end of Anna Maria Island. This island offers a blend of relaxation and convenience, being within walking distance of Bean Point Beach and Bayfront Park, as well as restaurants and shops on Pine Ave. It is also just a short drive from Tampa Bay.

The vacation rental has a user rating of excellent and can accommodate up to 6 guests. It features a chic living room with a large sectional for relaxation, an updated kitchen with granite countertops and essential appliances, and two bedrooms with king-sized cooling hybrid gel mattresses. Other amenities include air conditioning, a swimming pool, a garden, parking, and a shared laundry room and BBQ grill.