Holmes Beach Vacation Rentals

You are here No matter where you stay on Anna Maria island, you’ll experience beautiful views, especially from your Holmes Beach vacation rental. Spend time with the family at the local parks on the Manatee Public Beach or rent recreational equipment for loads of fun on the water! With miles of waterfront properties and homes in the neighborhood, you’ll find an Anna Maria vacation home that suits your needs anywhere on the island. Holmes Beach offers a small-town atmosphere with plenty of restaurants, shops, and nightlife activities away from the shore. Browse our Holmes Beach vacation rentals and book your island trip today!

Frequently Asked Questions

Where is Holmes Beach, Florida?
Holmes Beach is on Anna Maria Island, between Anna Maria and Bradenton Beach, along the Gulf of Mexico in Manatee County.

How far is Anna Maria Island from Orlando?
Approximately 2 to 2.5 hours via I-4 W and I-75 S.

What is Anna Maria Island known for?
Pristine beaches, crystal-clear waters, a laid-back atmosphere, historic landmarks, fresh seafood, and water activities like fishing, kayaking, and paddleboarding.

95 properties available

Highlights• 5-minute walk to the beach • Spacious backyard with Pool and Spa• Pet Friendly• Tiki hut and bar area Island Life by AMI Locals108 78th St Holmes Beach VRC#18-000083Welcome to Island Life, a fully renovated and updated vacation home with three bedrooms and two bathrooms. A private backyard tiki bar, a hot tub, and a heated pool await yo

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Stormalong Bay by Anna Maria Island Accommodations 308 56th St, Unit A, Holmes Beach, FL 34217 Welcome to Stormalong Bay by Anna Maria Island Accommodations, a vibrant two bedroom, two and a half bath vacation home with a bonus room, just a five-minute walk from the pristine sands of Holmes Beach. Perfect for families and groups, this island retrea

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South Seas by Anna Maria Vacations 307 A 66th Street, Unit A, Holmes Beach, FL 34217 VRC16-000311 Welcome to South Seas, a show-stopping three-level vacation home just a 5-minute walk to Holmes Beach! With six spacious bedrooms, four and a half bathrooms, and a private pool with an incredible waterslide, this luxury retreat is perfect for family

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Mermaid’s Retreat by Anna Maria Island Accommodations 104 29th St Unit 3, Holmes Beach, FL 34217 Welcome to Mermaid’s Retreat, a bright and inviting two-bedroom, one-bath Holmes Beach vacation rental by Anna Maria Island Accommodations, perfectly positioned just steps from the sugar-white sands of the Gulf of Mexico. This charming upper-level cond

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Gulf Pearl by AMI Locals 112 46th Street, Holmes Beach, FL 34217VRC21-000130Welcome to Gulf Pearl, an exquisite four-bedroom, three and a half bath vacation home on Anna Maria Island! This coastal paradise boasts a sparkling pool, relaxing in-ground spa, and an inviting backyard oasis with a tiki umbrella, poolside bar, and outdoor TV, the perfect

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Key Largo Cottage by Anna Maria Island Accommodations 315 62nd Street, Holmes Beach, FloridaDiscover the ultimate family getaway at Key Largo Cottage, a charming bungalow-style vacation rental perfectly situated along Anna Maria Island’s peaceful streets! This spacious home features three bedrooms, three modern bathrooms, and a private heated pool

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Addison’s Beach House by Anna Maria Island Accommodations 7203 Gulf Dr, South Unit, Holmes Beach, FL 34217 VRC16-000188 Welcome to Addison’s Beach House, your idyllic beach vacation escape just a three-minute walk from the breathtaking Holmes Beach on Anna Maria Island! This beautifully renovated, ground-level three-bedroom, two-bath home offers

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Addison's Beach House

Island Breeze by Anna Maria Island Accommodations235 64th Street, Holmes Beach, FL 34217Experience the perfect beach retreat at Island Breeze, a stylish three-bedroom, two-bath townhome just a two-minute walk from Holmes Beach’s pristine Gulf beaches! Perfect for relaxation or adventure, this coastal gem offers a private screened-in porch, outdoor

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Surf View by AMI Locals 209 54th St, Holmes Beach, FL 34217VRC18-000095Welcome to Surf View, an expansive eight bedroom, six bath luxury vacation home in Holmes Beach, perfect for large family gatherings, reunions, and group getaways. With a rooftop deck offering sweeping Gulf and Bay views, a resort style pool with waterslide and spa, and plenty o

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Pineapple Palms by Anna Maria Island Accommodations 308 64th St, Holmes Beach, FL 34217VRC17-000041Welcome to Pineapple Palms, the ultimate ocean-loving getaway just two-and-a-half blocks from the stunning beaches of Holmes Beach! Perfect for a small family or friends, this charming two-bedroom, two-bathroom home offers a private heated pool, lush,

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Simply Chic by Anna Maria Island Accommodations 214 67th Street, Holmes Beach, FL 34217 VRC16-000105 Discover Simply Chic, a stylish four-bedroom, three-bathroom ground-level vacation home located just a three-minute walk from Holmes Beach. Designed for relaxation and fun, this coastal retreat features a private pool, putting green, and outdoor ga

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Ob La Di Ob La Da by Anna Maria Island Accommodations 442 62nd St, Holmes Beach, FL 34217 Welcome to Ob La Di Ob La Da by Anna Maria Island Accommodations, a cheerful two-bedroom, two-bathroom ground-level retreat in the heart of Holmes Beach! This cozy bungalow radiates charm and good vibes, just like the iconic Beatles tune “life goes on.” Whethe

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