Picture yourself sipping a chilled glass of lemonade on a sun-drenched porch, the gentle sea breeze whispering through the palm trees, and the soothing sound of waves serenading your senses. Welcome to Anna Maria Island, Florida – a true slice of paradise! Here, we’re going to take you on a virtual tour of the top 10 coolest and most refreshing Anna Maria Island rentals for your next vacation. We’ve scoured the island’s private lagoons of luxury to bring you a handpicked selection of vacation rentals that will make your Florida escape unforgettable. So grab your swimsuits, slather on that sunscreen, and get ready for a stay that’s bound to make a splash!
A List of the Top Poolside Anna Maria Island Rentals
- Sirenia Beachhouse
- Coastal Breeze
- Fanta-Sea
- Coconut Cove
- Calico AMI
- Sandy Pants
- Pirates Bay
- Bateman’s Waterfront Home
- Blue Lagoon
- Sea La Vie\
- Beachside Pointe
- Lazy River Escape
- H2O Bungalow
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1. Sirenia Beachhouse
Experience the ultimate waterfront paradise at Sirenia Beach House! Nestled between two beautiful beaches and set on a tranquil cul-de-sac, this vacation rental is a water lover’s dream. With a private dock for fishing and boating, a kayak launch for aquatic adventures, and a resort-style backyard boasting a heated pool, spa, tiki huts, a mini-putt course and more, it’s a 5-star Caribbean escape. Relax on the outdoor decks, dine al fresco, or watch the game while floating in the pool. Inside, enjoy 4, plush bedrooms with 3 en-suite bathrooms, and even a Juliette balcony. Don’t miss the chance to unwind in this aquatic oasis!
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2. Cloud 9
Escape to Cloud 9, a luxurious 4-bed, 4.5-bath beachfront haven where shabby chic meets seaside elegance. Unwind in king-sized comfort, relish ocean views from the heated pool, hot tub, and covered porch. Explore the island with complimentary golf cart, bicycles, kayaks, and paddleboards. It’s not just a vacation; it’s an immersive experience. Book your 7-day minimum stay now and let Cloud 9 redefine your beachfront getaway with unparalleled luxury and outdoor bliss.
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3. Fanta-Sea
Indulge in paradise at Fanta-Sea! A 4-bed, 4-bath private oasis with a heated pool and your own beach volleyball court, just steps away from Gulf beaches. This renovated, ground-floor gem offers four bedrooms, four bathrooms, and a plethora of toys—from bikes to paddleboards. A golf cart awaits for island exploration. Grill up delights, soak in sunsets on the patio, and relish the playful dolphins at the North End of Anna Maria Island. A 7-day minimum stay awaits, promising the ultimate coastal escape. Book now and savor Fanta-Sea!
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4. Coconut Cove
Escape to the lavish tranquility of Coconut Cove, where luxury meets the comforts of home. On Anna Maria Island’s peaceful north end, this three-bedroom estate offers a short walk to the beach and local cafes. Enjoy a private resort-style pool, a putting green, and outdoor lounging spaces surrounded by swaying palm trees. Inside, find brand-new furnishings, a spacious kitchen, and multiple living areas perfect for families and large groups. Relax by the pool or on its sun shelf, unwind in the spillover spa, and savor the outdoor living area with two flat-screen TVs and a BBQ. Coconut Cove is your oasis in paradise!
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5. Calico AMI
Escape to paradise just 400 steps from the pristine beach! This exquisite home offers a tropical pool oasis with a waterfall, tiki hut, and family-friendly amenities. Experience luxury with an open layout, fully equipped kitchen, and bonus tower room. Enjoy Netflix on flat-screen TVs in every room, or unwind in the game room with ping pong and arcade fun. Conveniently located near shops and eateries, plus a private heated pool for ultimate relaxation. Your perfect beach retreat is here!
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6. Sandy Pants
Stay in style at this Holmes Beach gem, where your private heated pool and tropical patio await just moments from the Gulf of Mexico. With contemporary furnishings and vibrant accents, this multi-level house is a beach lover’s dream. Swim in the Gulf, explore Pine Avenue on the island trolley, and return home to relax on the deck or by the pool. Enjoy outdoor dining, the hammock, the pool’s waterfall, a gas grill, and indoor entertainment. With a range of 3 comfortable bedrooms to choose from, your island paradise awaits!
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7. Pirates Bay
On Anna Maria’s secluded North Shore lays Pirates Bay, a charming 2-bed, 2-bath beachfront home. This renovated ground-level retreat offers a private saltwater pool, direct Bay beach access, and enchanting views of the Sunshine Skyway bridge. Indulge in two king bedrooms, including a master suite with ensuite bath, and enjoy modern amenities like a fully equipped kitchen and cable TV. The highlight? An expansive waterfront pool deck leading to a sandy beach, perfect for kayaking or paddleboarding. Your beach getaway awaits at Pirates Bay – where relaxation meets coastal charm.
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8. Bateman’s Waterfront Home
Welcome to Bateman’s – a luxurious waterfront home on Anna Maria Island. This 4-bedroom, 4.5-bath gem offers 2543 sqft. of island paradise. Relax in the heated private pool with spa, outdoor bar room, and bonus games area. Boaters rejoice with a private dock, and the beach is just an 8-10 minute walk away. Indulge in the open layout, gourmet kitchen, and upscale furnishings. Elevate your island getaway at Bateman’s!
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9. Blue Lagoon
The epitome of island living at Blue Lagoon! This 2-bed, 2-bath duplex, just blocks from Pine Avenue, accommodates up to 6 with a sleeper sofa. A large shared heated pool awaits in your backyard oasis. Inside, find a fully stocked kitchen and comfy living area, while outside, the patio beckons with a gas BBQ and dining area. The expansive pool area is perfect for sun-soaked relaxation or entertaining. With separate entries, this home ensures privacy. Enjoy the convenience of a washer/dryer, WiFi, and a beach cart with chairs/umbrella. Unwind in style at Blue Lagoon!
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10. Sea La Vie
Luxury found at Sea La Vie Beach House, a 4-bed, 4.5-bath masterpiece on Anna Maria Island. This 2825 sqft. expanse boasts an open layout, gourmet kitchen, and en-suite bathrooms in every bedroom. The canal-front home offers a private pool, spa, and outdoor game room, creating the ultimate Floridian retreat. Smart-equipped and meticulously designed, this brand-new home invites you to unwind in style by the deep-water canal, just a short walk from Pine Avenue shops and restaurants. Your seaside escape begins at Sea La Vie!
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11. Beachside Pointe
Discover the perfect beach getaway at Beachside Pointe! This 2-bed, 2-bath condo offers a bright and spacious retreat in the heart of Holmes Beach. With a fully equipped kitchen, screened-in balcony overlooking the heated community pool, and easy access to the beach and island trolley, it’s an ideal family destination. Sleeps 6 comfortably, featuring a king master bedroom, a guest room with full and twin beds, and a queen sleeper sofa. Enjoy the beautiful scenery of the natural mangrove preserve, beach chairs, umbrellas, and the convenience of a washer/dryer.
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12. Lazy River Escape
Just a short stroll from the serene beaches, this newly remodeled duplex home offers the ultimate vacation experience. Enjoy the incredible lazy river pool, covered outdoor seating, and a wealth of amenities, including bikes, beach equipment, and a Nintendo Switch. Renovated with two new kitchens, stainless steel appliances, and granite countertops, our duplex provides comfort and convenience. With both sides available, it’s perfect for large families or can be rented separately. Experience worry-free relaxation in the most charming neighborhood!
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13. H2O Bungalow
The H2O Bungalow: a 3-bed, 3-bath delight. Immerse yourself in the unique backyard featuring your private lazy river that surrounds an island, waterfalls, hot tub, and tropical landscaping. Cookout on the grill, dine amidst the lush setting, and enjoy the fountains. Just two blocks from the Gulf beach, this dog-friendly retreat offers upscale interiors, a gourmet kitchen, and proximity to shops and restaurants. Your unforgettable Anna Maria Island escape awaits!
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Discover your dream poolside retreat with Anna Maria Island rentals on FLARBO. Whether you seek family-friendly fun or a romantic oasis, FLARBO offers the perfect vacation home rentals to make your island getaway unforgettable. Jump into the refreshing poolside paradise of your choice today! For your long-term trip to Florida, think about booking a vacation rental on a site that will allow you to “Book the Same Vacation Rentals for Less”.
Skip the traveler fees that are charged on other large online travel agency platforms like Airbnb, HomeAway, VRBO and Expedia. Reserve your vacation rental on FLARBO – Florida Rental By Owners where there are no booking fees for either traveler or property owners. FLARBO, it’s the best option for Florida travellers.
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