Anna Maria Island, Florida


Properties Available 392 properties available
Bask in cool coastal breezes and indulge in spectacular Gulf sunsets at this Bradenton Beach retreat. Perfect for a group getaway, this spacious six-bedroom getaway is comprised of upper and lower living spaces, each equipped with its own full kitchen, gas grill, patio, and a private washer and dryer to accommodate separate families. Located just a
Tropical Daze (290915)
Bradenton Beach, FL
House
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 18 guests
Overflowing with whimsical accents and colorful design, this Bradenton Beach duplex boasts a fantastic outdoor space, stunning Gulf views, and an unforgettable escape! Conveniently located just steps from the sand, spend your sun-filled days on the shore building sandcastles, paddleboarding, or embarking on deep-sea fishing adventures. Keep an eye
Beach Break (597666)
Bradenton Beach, FL
House
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Sunset Azul is a 2 bedroom/1 bath gulf-side ground level villa on the southern end of Holmes Beach. This unit has just been completely updated (October 2019) with all new floors, paint and beautiful coastal furnishings. It's quiet, yet close to shopping, restaurants and trolley stops. Best of all, this unit is only a few short steps to the white s
SunSet Azul by SeaBreeze Vacation (424828)
Holmes Beach, FL
Condo
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 6 guests
Two homes make for twice the fun at this inviting Holmes Beach hideaway! Comprised of twin duplexes, this convenient retreat offers double the living space and double the home essentials for friend groups or families traveling together. Gift shops, golf cart rentals, and great local food-and-drink options are within walking distance. The beach is a
Holmes Beach Bungalow (578725)
Holmes Beach, FL
House Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 12 guests
Come to historic Anna Maria Island and remember days gone by when you stay in this three-bedroom Key West-style cottage. With a sparkling cocktail-style pool, close proximity to the beach, dining, and Bayfront Park, you'll soon see why this beautiful rental is such a special place! You'll also have room for two cars in the driveway. The beach at Be
Harmony House (243783)
Anna Maria, FL
House
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Leave your responsibilities behind and fill your days with sun-kissed relaxation when you book your trip to this gulf-adjacent Anna Maria Island home. Boasting amenities like a shared pool, easy beach access, a communal sauna, and one parking spot, this home makes it a piece of cake to slip into vacation mode! Nestled in the Water's Edge Communit
Water's Edge 105 South (250522)
Holmes Beach, FL
House
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 2 guests
Look no further for your next home-away-from-home, as this coastal escape has everything you need to feel welcome and relaxed in no time mere blocks from the beach. Pack a picnic and walk to sugar-white sand as soon as the sun comes up. When you want to cool off a bit, return to home base and take a dip in the private pool with a favorite beverage
Mermaid Sunset (272835)
Holmes Beach, FL
House
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Anna Maria Beach House offers a 5 bedroom and 6.5 bathroom, pet-friendly property, making it a perfect vacation retreat for your whole family. Situated close to the beach, shops, and restaurants, this property is an ideal choice. Just a brief stroll away from the beach, the house boasts a pool and hot tub for your enjoyment. Cap off your day by hea
Anna Maria Beach House by SeaBreeze Vacation (597340)
Anna Maria, FL
House Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 7 baths
Guests 8 guests
Come live the island life when you stay in this charming 'Old Florida' style cottage with a private saltwater pool and close proximity to the beach. You'll also have room for three cars in the roomy carport and access to Anna Maria's free trolley. With only one house between you and the glittering quartz sand on the Gulf of Mexico, start your morni
Mangrove Cottage (243786)
Anna Maria, FL
House Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Whether you're hanging ten or just hanging loose, this breezy suite in the heart of Holmes Beach is the ideal choice for your next Gulf Coast getaway! From the beach only a short stroll away to a fantastic array of bars, restaurants, and local shopping options, the best of Anna Maria Island and its bustling nightlife is at your doorstep. You'll als
Longboard (580138)
Holmes Beach, FL
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 1 baths
Guests 6 guests
Welcome to your dream vacation home on Anna Maria Island - a luxurious 5-bedroom, 4.5-bathroom canal front retreat that promises an unforgettable getaway! Beach à la Mode is an exquisite newly built property that offers a perfect blend of comfort, style, and convenience for your ultimate vacation experience. Located just a short 7-minute walk from
Beach a la Mode | Luxury Canal Front Home on AMI w/ Private Pool & Spa (310721)
Anna Maria, FL
House
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 8 guests
The Beach Sands condo is completely surrounded by water with the Gulf of Mexico to the west, the Intra-Coastal Waterway to the east, Tampa Bay to the north and Sarasota Bay to the south. The Beach Sands offers the best location on Anna Maria Island where the island is only 150 yards wide. Our complex stretches from the Gulf to the Intra-Coastal Wat
Anna Maria Island Beach Sands (301993)
Bradenton Beach, FL
United States - FL - Bradenton Beach
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests

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