Imagine waking up to the sound of gentle waves and golden sunrises over the Gulf of Mexico. Welcome to Holmes Beach on Anna Maria Island, Florida, where charming cottages and luxurious beachfront homes await. We’ve curated the top Holmes Beach rentals, each offering unique amenities, stunning views, and easy access to the island’s best attractions. Whether you’re planning a romantic getaway or a family holiday, these rentals promise an unforgettable stay. Dive in to discover your perfect home away from home!
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The Best Holmes Beach Rentals
- Blue Sky Beach House – 5 Bedroom Vacation Rental
- Beach Paradise 5 – 2 Bedroom Vacation Rental
- Dream Weaver – 3 Bedroom Vacation Rental
- Luum at the Shore – 3 Bedroom Vacation Rental
- Swanky Bubbles – 9 Bedroom Vacation Rental
- Sea Dreams – 3 Bedroom Vacation Rental
- Sunset Shores – 2 Bedroom Vacation Rental
- Mariner’s Crossing – 6 Bedroom Vacation Rental
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1. Blue Sky Beach House
Experience luxury at Blue Sky Beach House, just a block from Anna Maria Island’s beautiful beaches. This 5-bedroom, 4-bathroom home features a private heated pool and spa, rooftop deck, coastal decor, and an open floor plan perfect for families or groups. Kids will love the bunk room, games, and puzzles. With top-notch amenities and a prime location near shops and restaurants, it promises a stress-free, unforgettable vacation. Book now!
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2. Beach Paradise 5
Stay at Beach Paradise 5, a beautifully renovated condo steps from the Gulf’s stunning sunsets. This 2-bedroom, 2-bathroom gem features a fully equipped kitchen and a private sun deck. Enjoy nearby shops, eateries, and the legendary Skinny’s Place for the best beach burgers and beer. With easy access to the free Island Trolley and local attractions, it’s perfect for a relaxing, adventure-filled getaway on Anna Maria Island.
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3. Dream Weaver
Escape to Dream Weaver, a custom luxury home in Holmes Beach, offering 3 oversized bedrooms and resort-style amenities. Relax in the infinity pool and spa, or enjoy family time in the spacious living areas. With a gourmet kitchen, elevator, and outdoor entertainment, including a 4K TV and putting green, it’s the ultimate retreat. Just a 7-minute walk to the beach, it’s perfect for your next family vacation!
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4. Luum at the Shore
Embark on a wellness journey at Luum at The Shore, where every detail fosters serenity and eco-conscious living. From organic mattresses to solar-powered shades, this 3-bedroom oasis offers luxury with a conscience. Indulge in Bali-inspired design, enjoy high-end appliances, and savor the convenience of provided organic products. Elevate your vacation experience with thoughtful touches and flexible cancellation policies. Book now for a transformative retreat on Anna Maria Island!
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5. Swanky Bubbles
Discover Swanky Bubbles, a luxurious 9-bedroom retreat accommodating up to 18 guests, steps from the beach. With spacious living areas, fully equipped kitchens, and ensuite bathrooms, comfort is paramount. Enjoy the private pool, swim-up bar, and rooftop deck for ultimate relaxation and entertainment. Benefit from professional linen services and thoughtful amenities. Make unforgettable memories with family and friends in this ideal vacation haven!
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6. Sea Dreams
Experience coastal paradise at Sea Dreams! This 3-bedroom home boasts a crystal blue pool, a putting green, sun deck, and space for your boat, offering the ultimate relaxation and waterfront living. Enjoy coastal decor, stainless steel appliances, and ample seating. With beach equipment provided, enjoy sun-soaked days by the sea. Benefit from professional linen services and thoughtful amenities. Create unforgettable memories in this dreamy retreat for a vacation you’ll never want to end!
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7. Sunset Shores
Experience oceanfront luxury at this newly remodeled, pet-friendly 2-bedroom cottage! Just steps from the Gulf of Mexico, it features a cozy living room, a fully stocked kitchen, and stunning sunset views. Relax on the wrap-around balcony, grill your favorite meals, and enjoy easy access to top beaches and local eateries with a complimentary golf cart. Sleeps up to 6 people! With high-speed Wi-Fi, smart TVs, and beach essentials included, this charming retreat offers everything you need for an unforgettable getaway.
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8. Mariner’s Crossing
Experience coastal elegance at Mariner’s Crossing on Anna Maria Island! This luxurious home features stunning Gulf views from almost every room, a rooftop deck, and a private heated pool with a spa. With six king bedrooms, a fully equipped kitchen, and beautifully decorated living spaces, it’s perfect for family gatherings. Enjoy alfresco dining, the game room, and easy access to local attractions at Mariner’s Crossing!
It’s great to get inspiration for holidays on Florida Rental By Owners. You can also get inspired through digital magazines that specialize in coastal retreats like Sugarsbeach.com who also showcases our holiday rentals.
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Whether you’re planning a family reunion, a getaway with friends, or a relaxing escape, our top Holmes Beach rentals offer the perfect combination of luxury, comfort, and convenience. From stunning Gulf views to private pools and beautiful interiors, each rental promises an unforgettable stay on Anna Maria Island. Explore the best of Holmes Beach and make your next vacation truly special.
Book your dream home today and start making lasting memories!
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