Featured Anna Maria Island Rentals and Bradenton Rentals

Porch and pool area of a vacation rental on Anna Maria Island

Embrace the allure of summer with our exclusive Anna Maria Island and Bradenton area rentals! This season, explore our diverse collection of properties, from quaint beachfront villas to expansive luxury homes, some offering newly discounted rates. Our portfolio extends to the city of Bradenton, Florida, renowned for its lively arts community and scenic parks, Longboat Key, and beyond.

To make your stay even more unforgettable, our Anna Maria Island rentals come equipped with an array of amenities to cater to your comfort and pleasure. Enjoy the convenience of fully equipped kitchens, perfect for home-cooked meals, and unwind in private pools after a day soaking up the Florida sun. Each rental encapsulates a unique fusion of homely comfort and upscale luxury, guaranteeing a vacation you'll cherish. Conveniently situated, these properties provide easy access to local attractions, retail boutiques, and gourmet eateries, ensuring your adventure never ends.

Our experienced Reservations team, available at 941-757-8226, is eager to help you find your perfect vacation home to enjoy a visit to Anna Maria Island and Bradenton.

25 properties available

Kismet by the Sea by AMI Locals Experience your perfect island escape at Kismet by the Sea, a charming three-bedroom, two-and-a-half-bathroom villa just a short walk from Anna Maria Islands beautiful Gulf beaches! Nestled in the heart of Holmes Beach, this coastal retreat features relaxed boho decor, a shared pool, private balconies, and endless n

Tidal Daze by AMI Locals VRC22-000087 Welcome to Tidal Daze! This four-bedroom, three and a half bath Anna Maria Island retreat is just a two minute walk to the soft sands of Holmes Beach. With a private pool, putting green, outdoor games, and multiple lounge areas, this home was designed for family fun and relaxation. Whether you’re soaking up the

Bradenton Beach Club 232 by AMI Locals Vacation Rental License #TPL22-000091, CND5105469Welcome to Bradenton Beach Club 232, a two-bedroom plus den, two-bath vacation condo offering the perfect blend of comfort, convenience, and coastal charm! Located in the tropically landscaped Bradenton Beach Club community, this retreat provides direct beach ac

Bradenton Beach Club 232

Casa Bella by AMI Locals VRC22-000114 Experience the ultimate island retreat at Casa Bella, a luxurious corner lot vacation home located just three blocks from the pristine Gulf in Holmes Beach. This stunning four-bedroom, three-bath home offers modern coastal elegance, a private pool, and easy access to parks, beaches, and local attractions. Perf

Blue Coral Beach House by AMI Locals VRC23-000024 Welcome to Blue Coral Beach House, a vibrant four-bedroom, three-bath coastal casita located in a quiet neighborhood of Holmes Beach! Just a 7-minute walk from the white sand beaches and sparkling ocean waters, this beautifully styled home features lush landscaping, a private heated pool, and a je

Blue Coral Beach House

Serenity at Bay Palms by AMI Locals Discover the charm of Anna Maria Island at Serenity at Bay Palms, a newly updated coastal retreat just a short walk from the stunning Gulf beaches on Anna Maria Island! This four-bedroom, four-ensuite bath home offers modern luxury, a private heated pool with in-ground spa, and easy access to local dining, shopp

Serenity at Bay Palms

Mermaids Watch by AMI LocalsVRC18-000086Welcome to Mermaids Watch, a beautiful ground-level bungalow just minutes from Holmes Beach and Anna Maria Island’s stunning Holmes beach! This three-bedroom, two-bath retreat offers a private heated pool, in-ground spa, lush landscaped backyard, and comfortable coastal decor that blends Old World Florida cha

Welcome to Bayfront Retreat, a boater's paradise with a private dock on the bay, a sparkling pool and spa overlooking passing boats, and a stunning rooftop deck! This expansive five-bedroom, five-and-a-half-bath luxury beach home is perfect for water sports enthusiasts, fishers, and beach lovers seeking comfort, style, and spectacular views. Locate

HOT 136

One Happy Condo by AMI Locals Enjoy the luxury of Florida's Gulf Coast at One Happy Condo, a beautifully designed three-bedroom, three-bathroom condo located in the exclusive gated community of Harbor Isle Margaritaville Resort! This home features resort-style amenities, ocean views, and vibrant coastal decor, just one mile from the famous beaches

Palmetto Pointe by AMI Locals Vacation Rental License #VR19-000033 Welcome to Palmetto Pointe, a luxurious five bedroom, five and a half bath vacation home located just one block from Anna Maria Island Beach. This retreat features a rooftop deck with Gulf views, wraparound balconies, a large private pool with spa, and spacious bedroom suites; perfe

The Deckhouse by AMI Locals Vacation Rental License #VR20-000007 Welcome to The Deckhouse, a beautifully remodeled three bedrooms, three bathrooms home just three houses from the beach! With a brand-new heated pool and spa, multiple deck spaces offering Gulf views, and a stylish coastal interior, this luxury Anna Maria Island rental is perfect for

Oar House by AMI Locals Welcome to Oar House, a new 6-bedroom, 7-bath luxury home right on Pine Avenue on the north end of Anna Maria Island. It is made for easy group getaways, with a private heated pool, a large spa, and a rooftop deck with wide water views. You will also find plenty of fun, resort-style amenities. Step out the door to Pine Avenu

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